Keys Sea Heritage Journal

VOL. 25 NO. 1 FALL 2014 USS SHARK

OFFICIAL QUARTERLY PUBLICATION OF THE KEY WEST MARITIME HISTORICAL SOCIETY Dope Den on Duval Street. Following letters are from the Scott De Wolfe collection and were transcribed by Mary Haffenreffer. They include letters from Mrs. Gray L. O’Brien, also known as Mrs. W.D. Cantrell, writing to her husband in jail in Dade County in June 1921. One or more of the letters containing morphine were confiscated by law enforcement Mrs. O’Brien appears to have been a player in a major drug operation in Key West. The article incudes correspondences when the letters were confiscated by federal officials who forwarded them to the appropriate agency for investigation. Local law enforcement agencies were not included in any of the correspondences because the lack of trust. As often happens in history research, the whole story could not be found. A search of local records and of Miami newspapers failed to find any reference to this incident. The Jefferson Hotel in the 100 block of Duval Street. Photo credit: Monroe County Library. Special Agent in Charge dope charge. His time will be up in DEPARTMENT OF JUSTICE a few days, and there is now a check Bureau of Investigation Dear Sir: here to pay his fine. I have asked Miami, Fla. Enclosed are letters which were Moritz to delay collecting the fine intercepted this date by Deputy until day after tomorrow. June 4, 1921 Marshall Moritz. They were written As the thick letter indicates, Mrs. by Mrs. Gray L. O’Brien to her O’Brien is on the inside of a dope Howard P. Wright, Esq., husband, who is now in the county ring at Key West. The Manuel A. Box 32, Jacksonville, Fla. jail serving time on a possession of (Continued on page 3) SocietyNews by Tom Hambright of the war. The G.A.R. promoted voting rights for then called “Negro”/”Colored” black veterans, as many white veterans recognized their demonstrated patriotism and sacrifices, providing one of the first racially integrated social/fraternal organizations in America. Key West remained in the Union The Florida Keys Sea Heritage during the Civil War and after the Journal is published quarterly. war local veterans formed a unit of Subscription is available through the G.A.R. post named Major B.C. membership. Copyright 2014 by Lincoln Post No. 13, which in the the Key West Maritime Historical late 1800s may have been one of Society of the Florida Keys, Inc. the few integrated organization in The art on the masthead, the USS the state. The G.A.R. is listed in the Shark, was drawn by Bill Muir. A newspaper article with the with the city directories with the officers. The partial list of the G.A.R. listing in Maloney’s 1900 Directory Editor: Tom Hambright showed Dr. J.W.V.R. Plummer, PC; Anyone that studies history will Frank Shavers, S V C; Henry Colson, tell you that sometime you cannot J V C; James A. Roberts, adjt. Letters and articles are welcome. find the rest of the story. Our front After years of searching for more Please write to: Editor, Florida Keys page article is such a story, but information on the local unit of Sea Heritage Journal, KWMHS, there is a enough information for a the G.A.R. without success when P.O. Box 695, Key West, FL look at the drug trade in 1921. I found the above partial article in 33041 or visit our web site I have searched for years for the the Scott De Wolf Collection which Keywestmaritime.org. membership of The Grand Army list some of the original members of of The Republic in Key West. the Major B.C. Lincoln post being The Grand Army was a fraternal Key West Maritime installed by Frank N. Wicker, who Historical Society organization composed of veterans was Collector of Custom from 1873 Board of Directors of for the to 1883. Several more searches of Northern/Federal forces. Founded the De Wolf Collection has failed President: Corey Malcom in 1866 in Decatur, Illinois, and to find the missing piece, so far no Vice President: Bill Verge growing to include hundreds of luck. Secretary: Andrea Comstock posts (local community units) The members of the G.A.R. in the Treasurer: Tom Hambright across the nation, (predominately artical are: William H. Wood, John in the North, but also a few in the Williams, D.B. Mathews, Moses George Craig South and West), it was dissolved Thomas, John Scheurer, George H. J. Gregory Griffin in 1956 when its last member, Wood, Tony Laurie, Henry Linter, Bill Grosscup Albert Woolson (1847-1956) of Thomas Ponshot, Charles Williams, Mary Haffenreffer Duluth, Minnesota, died. Linking John Fletcher, Stepney Austin, Clark Sheri Lohr men through their experience Yarwood and Moses Crawford. Bruce Neff Wendy Tucker New Members John Viele Robert J. Wolz Peter Admas, Glenwood, MD; Mr. & Story, Dividson, NC; Alan Teitelan, Mrs. T.M. Arrasmith, Washington, Key West; Richard Vaughan, Kansas David Harrison Wright DC; Max Foster, Riverview, FL; City, MO; Alvin Whitaker, Waterloo, Herb Martin, Longwood, FL; James WI.

2 - FLORIDA KEYS SEA HERITAGE JOURNAL - FALL 2014 (Dope from page 1) I am sending some DeCastro is the Cuban who was Department of Justice correspondence turned over to me caught here some time ago with Bureau of Investigation today by Special Agent D. of J. a large quantity of morphine, and Miami, Fla. No doubt there is something to it who was recently sentenced (very but Key West is a hard place to get lightly). The Murphy mentioned is June 8, 1921 results. Joe Krause, who was also recently Respects, released from jail on a liquor charge. Howard P. Wright, Esq., There is little doubt that Krause and Box 32, Jacksonville, Fla. W. J. Maloy DeCastro are in Cuba to get a load Narcotics Inspector of dope. Dear Sir: You will also note the “one big block,” this being a large block of Gray L. O’Brien and wife alias TREASURY DEPARTMENT morphine crushed. This was sent Mrs. W. D. Cantrell Internal Revenue Service through the mails. The reference to Atlanta, Ga. “Garcia at the Victoria” means one Enclosed herewith are more of the Cuban waiters at the Victoria letters in one of which is some June 10, 1921 Restaurant in Key West. This man is morphine, and in another, a Office of Supervising Federal a dope seller. reference to sending the morphine. Prohibition Agent The O’Briens ran a dope den here Enclosed also is a note to Dr. L. Gulf Department all winter, and the arrest of O’Brien H. Martin, signed by B. C. Taylor, caused him to become acquainted a prisoner in the county jail. This HGJ. with Krause and DeCastro, while note was taken from the lining of all were in jail. The police recently the clothing of O’Brien when he Mr. C. E. Miller closed the house, and ordered was released from the County Jail Narcotic Inspector Krause and Mrs. O’Brien out of this morning on payment of a fine Atlanta, Ga. town. The Mitch mentioned is a by his wife. Miami dope runner who has never Kindly refer these matters to the Sir: been caught. nearest narcotic inspector. Enclosed you will find Kindly refer this matter to a information transmitted to this narcotic inspector, and impress Respectfully, office by Narcotic Inspector W. J. upon them the fact that they must Maloy. take immediate action if they wish Leon E. Howe In course of your investigations to catch DeCastro and Krause. I Special Agent in Florida please give this due suppose there will be no trouble attention. catching Mrs. O’Brien. She is TREASURY DEPARTMENT stopping at The Jefferson Hotel in Internal Revenue Service Respectfully, Key West under the name of Mrs. Atlanta, Ga. W. D. Cantrell. Jacksonville, Fla. W. J. Drautzburg (signed) You might warn the narcotic Head, Narcotic Unit, people not to go near the Federal Office of Narcotic Division Building, particularly the Customs. SUPERVISING FEDERAL Gulf Department. If possible they should not travel on PROHIBITION AGENT a ticket indicating “govt. request” GULF DEPARTMENT DEPARTMENT OF JUSTICE as they will be tipped off by the Bureau of Investigation railway conductor. June 9, 1921 407 - 9 - 11 Bisbee Building Jacksonville, Fla. Respectfully, Hon. D. J. Garett S. F. P. Agent June 14, 1921 Leon E. Howe (signed) Atlanta, Ga. Special Agent (Continued on page 4) Sir:

FALL 2014 - FLORIDA KEYS SEA HERITAGE JOURNAL - 3 (Dope from page 3)

D. J. Ganett, Esq. Supervising Federal Prohibition Agent, Federal Building, Atlanta, Ga. Dear Sir:

Re: GRAY L. O’BRIEN AND MRS. W. D. CANTRELL, Narcotic Matter.

I am enclosing you copy of letter from Special Agent Howe, of this An envelope from the Jefferson Hotel used by Mrs. W.D. Cantrell. Photo credit: office, dated June 8th, attached to Monroe County Library. which are several letters from Mrs. W. D. Cantrell, Key West, Fla., I am enclosing you herewith just count the days until I can see addressed to G. L. O’Brien, General some correspondence which is self- my Daddy. Dear, I love you more Delivery, Miami, Fla. It will be explanatory. and more each day. I am sick. noted that one of these letters Give the same such attention as Came so Friday and of course can’t contains several grains of powered you think it deserves. make any money for a day or so morphine sent through the mail. but will send you some tomorrow. Several similar letters containing D. J. Garrett (signed) Am sending you the receipt for the morphine were turned over to Supervising Federal Prohibition Lights. You can notify them to take Dr. Maloy, Narcotic Agent, by Agent. the meter out and get five dollars on me, several days ago, but I have that. If you need anything just let been unable to get in touch with your Baby know and she will see Dr. Maloy since that time and am The Jefferson that you get it at once. I just think of therefore sending these letters direct Key West, FLA. 29th you all of the time and dream about to you. My Own Dear Daddy, at night. Do you ever think of your Have not heard from you as yet Poor Little Baby way down here by Yours very truly, but hope I will do so by tomorrow. herself with no one to love her or How is my Daddy feeling? I do look after her at all? I do miss My Howard P. Wright (signed) hope you are well. Don’t you now Daddy so awful much. I want you Special Agent in Charge that little Old Jew is down here. to promise me that when you get out Followed me right on down here. I of there you will come to me on the HPW:B jumped on him about that other and first train that runs this way. Won’t encl. he denied everything of course but I you do that for me? Write and tell am not going to trust him anymore. me that you will tell me exactly the TREASURY DEPARTMENT Am having lots of trouble getting day you expect to get out so I can Internal Revenue Service The Stuff but will have it for sure look for you. Well, I am going out Atlanta, Ga. tomorrow. Lopez has been getting to supper and OH! How I wish you me just a little bit every [?] from were here to go with me but you June 15, 1921 a Dr. They have to wait for the will be before very long, won’t you boat from Cuba. As soon as I get Dear? I will write again tomorrow C.E. Miller Esq., it I will send you some. Will also and send those things to you. Narcotic Agent, send some “C” so as my Daddy can Answer at once and tell me how Jacksonville, Florida enjoy himself a little bit. Anyways, much you Love Your Baby. I want to see you so awful bad I With all my Love Sir: don’t know what to do. I get so lonesome and blue I nearly die. I The Jefferson

4 - FLORIDA KEYS SEA HERITAGE JOURNAL - FALL 2014 Key West, FLA. him at the train the day I left. I all I can use for myself and you was with Mitch and Mitch gave and he sells me the 25 gram boxes Dear Daddy, me $5.00 but no one else gave for $25.00 per box so we ought to What is the matter? Have not me one penny. See Mitch and make some money with it when you heard from you since Friday and I ask him all about it if you can’t come down here. He sure has been have written every day and sent two believe me. Do you want to take nice to me. Gives me all my meals wires. I was sure I would hear today a perfect stranger’s word to your and he have me an awful pretty hat but did not. Please write me and let own Baby’s word? It sure does yesterday. Bought it and sent it to me know what is wrong. Am wiring nearly kill me for you to treat me but it looks fine on your Baby you ten dollars today for railroad me that you and I have always and we are going to get me a dress fare. Be sure and get the money from stuck to you through everything today. I look like a tramp now but the Gas and Lights. Let me know if and always tried to treat you right you won’t know your Baby when you need anything at once. Am also and done all I could for you and you see her. I am ashamed to go on sending something else in another always will as long as you will the streets. I make him think I am letter. Please write me at once and let me. Please, Daddy, don’t go sick so he sends me my meals to my let me know when you are coming. back on your Baby, if you do it room and is so nice to me. When I Come just as soon as you get out on will just kill me for I have given get fixed up I can make some good the first train that runs for I do not up everything I hold dear in this money here in the hotel. Listen, want to see you so awful bad and I world for you but I don’t regret it Love, Big A’s place has closed up love you so good so please come to one bit – only wish I had more to on account of her Daughter dying me as soon as you can and I will see give. I would even give my life if and they locked her up for killing that you get everything that you want. it would help you in any way. You her daughter. She took too much of Write at once. know I would. Please, Dear, if you “M” and “C” mixed. Don’t know Always yours, have any love at all left for me, for what they will do with her. They got Baby God Sakes, don’t write me like all of her girls, too. Most of them that anymore. I am almost crazy use it, too, and they took all she had now and I am so sick I cried all that is why it is so scarce here now. The Jefferson night long. Thinking about you, is Well I know you are tired of reading Key West, FLA. there any one person in this world this but it is just pouring down rain My Own Dear Daddy, that has as much trouble? I guess outside and I am so lonesome and Oh! Daddy how could you write the Lord is punishing me as you blue for you. Listen, Dear, I want to your Baby like you did? It almost said he would but it is almost too you to see Mitch and ask him about broke my heart when I read your letter much for me to stand. I have not that and you and also send your yesterday. It is hard enough for me to been able to make any money, friend down here and ask anyone have to be away from you and then to have been sick since Friday, have you want to about me and I am sure think that you doubt me like that. You my hotel bill to pay and there is you will find out I am not lying to know I have always been true and no Stuff in town. I have been you and am willing to do anything square to you and it sure does hurt getting just a few little pieces at a you want me to. All you have to do me for you to talk that way for you time from Dr. They are expecting is just say so. Now, Dear, I want you know you are all I have left - to have some in every day from Cuba so I to write me at once and tell me you me and if you go back on me I will have been suffering and worrying are not mad with your Baby and you just kill myself for I love you better for that. Don’t know where the Love me a little bit. I have written than my life and I can’t live without next Shot is coming from. You you every day since I came. Don’t you. I will tell you why Joe told you know how it is - what you take know why you don’t get them. Will that. He asked me to stay with him don’t do any good but I will be send you $5.00 in another letter and I refused and he got mad so now fixed tonight and can get all I along with this. One it is all I have. he is trying to put you against me. I need of both and it won’t cost Will send more tomorrow with wrote you that Murphy was here but me anything, not one cent. I have something else. I will swear I never went with him at only one real friend here and that all. He and Manuel left Sunday for is Garcia at the Victoria. He will With all my love, from your Cuba to stay. He was only here two get in a supply and as long as I own, days. Dear, I swear I never spoke to treat him nice he will give me Baby

FALL 2014 - FLORIDA KEYS SEA HERITAGE JOURNAL - 5 Filibusters in the Keys

By John Viele proclamation, many Americans general finally decided to go ahead. were sympathetic to the Cuban As the general’s boat hit the beach, It is midnight, Christmas Eve, rebels’ cause. While a few joined the fort opened fire on the landing 1896, as a large unlit ocean-going the fighting in Cuba, others, party and on Three Friends. When tug cautiously feels her way towards motivated in part by financial gain, Broward’s crewmen refused to row a low-lying Key and drops anchor. took risks to ferry Cuban patriots any more fighters to shore, Broward Crewmen lower several boats and and arms from the U.S. to Cuba. In said he would do it himself. With load them with case after case of cities with large Cuban populations that, some of his leading crewmen rifles, ammunition, explosives, like Key West, Jacksonville, and said they would take the chance. and machetes. Spanish speaking New York, Cubans formed clubs Then Broward sighted a Spanish men climb down into the boats to raise money to support the approaching at high and clumsily row and then drag revolution, particularly to provide speed. He ordered a deck hand to the boats across a mile of shallow money to outfit and finance cut the anchor line and, as soon as water to the island. The boats move filibuster expeditions. In the the returning boats hooked on to steadily back and forth between the annals of filibustering, two men the davit falls, got underway. The tug and the shore through the night and two vessels stand out above gunboat commenced firing. Seeing and into the morning. Finally at the rest. They were Napoleon no way to escape, Broward told his noon, as the last boat departs, the Bonaparte Broward, who later crew he intended to ram the gunboat tug weighs anchor and runs rapidly became governor of Florida, and and all hands should prepare to out to open water. Left on shore, the tug Three Friends, and captain swim ashore. Just at that moment, collapsed among the mangroves, are “Dynamite” Johnny O’Brien and he remembered the big pine-wood forty-five exhausted men oblivious the tug Dauntless. knots piled on deck. He called to his to their surroundings. While most of the filibuster men to throw the pine knots in the The men and cases of arms and runs made by these two captains boiler furnace. A huge dark cloud of ammunition had landed on No originated in Jacksonville and other smoke belched from the tug’s stack. Name Key, just east of Big Pine north Florida ports, the Keys played Concealed by the smokescreen, the Key. They were a group of forty an important role in their operations Three Friends escaped. Cuban patriots and five Americans, as rendezvous harbors, escape On a subsequent run, Broward two of them reporters for major havens„ and arms caches. On his was scheduled to meet the newspapers, on an expedition to first filibuster run, Broward raced paddlewheel steamer City of Key help free Cuba from the yoke of the Three Friends out of the St. West carrying 449 cases of arms Spain. A Cuban revolution had Johns River under cover of darkness off Alligator Light. But before the begun in 1895 and was still ongoing to escape a revenue cutter on the rendezvous could be effected, a at the start of the Spanish-American lookout for him. At Indian Key, he revenue cutter surprised the two War in 1898. rendezvoused with two schooners vessels and ordered them into Key Soon after the start of the Cuban carrying arms, ammunition, and West to be searched. The more- revolution, President Cleveland sixty-five Cuban patriot volunteer than-tolerant Key West inspectors declared the U.S. would remain fighters. By previous arrangement, found several cases of arms on neutral and instructed collectors a Cuban pilot was taken aboard to board Three Friends, but decided of customs and the Revenue guide the tug to the planned landing there was not enough to constitute Marine (forerunner of the U.S. place. After almost causing the tug an “armed expedition.” and she was Coast Guard) to be on guard to to run aground, he piloted the tug released. Because the City of Key prevent armed expeditions bound into a bay and announced it was the West was not suspected of being for Cuba from leaving U.S. ports. proper place. But Broward sighted a involved in filibuster operations, These illegal attempts to support small fort and a village on the shore she was also let go. the Cuban rebels were known as not too far distant. He conferred with Undaunted by his narrow escape, filibuster expeditions. the Cuban general as to whether Broward immediately proceeded to Despite the President’s to proceed with the landing. The an unnamed key, probably Bahia

6 - FLORIDA KEYS SEA HERITAGE JOURNAL - FALL 2014 Honda, loaded forty-five Cuban volunteers, plus a large store of arms and ammunition, and successfully landed them in Cuba. As the Three Friends neared Key West on her return, she was sighted and chased by the US Navy cruiser USS Raleigh. Moving through a shallow passage in the reef where the cruiser could not follow, Three Friends once again escaped. According to one source, spectators on rooftops in Key West cheered The successful runs of Three Friends, Dauntless and other filibuster vessels were no secret. In fact, Broward was given a public hero’s welcome in Jacksonville when he returned from his second expedition. In the face of this, President Cleveland issued a second, sterner anti-filibuster order. He ordered more revenue cutters and two Navy cruisers to patrol Keys waters. Pinkerton and Treasury detectives followed the filibuster captains. More detectives, hired by the Spanish government trailed the senior Cuban military officers. General Weyler, commander of the Spanish forces in Cuba, offered a $25,000 reward for the capture of any filibuster captain, dead or alive. With the risks becoming greater, the Cuban revolutionary groups were having trouble recruiting vessels and captains. The answer to their prayers came in the form of a daring Irish seaman, “Dynamite” Johnny O’Brien, and a tug with the reputation of being the fastest in the south, the Dauntless. By early fall of 1896, O’Brien Napoleon Bonaparte Broward. Photo credit: The Author. had made five successful landings in Cuba and earned enough money seized the Dauntless on her return patriots, there were three Americans to recoup the cost of the tug. To from Cuba in September. on board. Two were newspaper avoid arousing suspicion, O’Brien With Dauntless temporarily reporters, Ralph Paine and Ernest and Cuban liaison officers would out of action and Broward under McCready, the third was an ex-U.S. debark the tug on the return voyages close watch, O’Brien was assigned Navy gunner’s mate. Mike Walsh. and row ashore to Key West. Despite to take Three Friends on the next these precautions, a revenue cutter run. In addition to forty Cuban (Continued on page 8)

FALL 2014 - FLORIDA KEYS SEA HERITAGE JOURNAL - 7 (Filibusters from page 7) drifted to a stop and hoisted a red Walsh and several others rowed While navigating the tug’s way lantern to signal that she was out to Big Pine Key and returned with into the mouth of the San Juan River action and needed help. The other some water and bananas. for a night landing, O’Brien saw the two abandoned the chase The next day, a schooner, dim image of a Spanish gunboat to come to her aid. In the only naval dispatched by the Cuban waiting for him. He immediately engagement of filibustering, Mike revolutionary club in Key West, reversed course and rang up full Walsh’s shot had saved the members arrived with food and water. speed. Because her boilers were of the expedition from almost Ralph Paine, the adventuresome fouled with grease and salt, the tug certain capture and execution. newspaper correspondent, and his could not make her top speed and O’Brien could not afford to reporter friend decided to go to the gunboat drew slowly closer. As reenter a US port with the arms Key West and hired the schooner the tug exited the bay, O’Brien saw and rebels on board, so he decided to try to find out what was going two more gunboats, one to the east to deposit them temporarily in the to happen to the expedition next. and one to the west, closing on him. Keys. This was the Christmas eve After contacting members of the It was apparent that the expedition’s landing on No Name Key. After Cuban revolutionary club, they plans had been leaked to the enemy. leaving No Name, O’Brien left were able to wire their stories of When the first gunboat was about Three Friends and made his way the engagement with the Spanish a half mile astern of the tug, she to Key West aboard a chartered gunboat to their newspapers. opened fire with her one-pounder sponge schooner. He told the Cuban Later at the Cuban club, Paine guns. Fortunately for Three club about the men and munitions learned that the stories of the Three Friends, the Spanish gunners were he had left on No Name and then Friends engagement with the poor marksmen. took passage to Tampa aboard a Spanish gunboat had been widely O’Brien ordered the Hotchkiss passenger steamer. publicized. When the tug stopped twelve-pounder field gun to be During the landing on No Name, to replenish her coal supply in Key broken out of its packing case. one of the small boats had been West she was seized by customs Navy gunner Mike Walsh, seeing blown off its course by the rising officials. Later that day came the gun, shouted up to O’Brien morning wind. Mike Walsh was the intelligence that O’Brien had “If you’ll let me handle it, I’ll in the boat. As he swore at his reached Jacksonville and managed guarantee to produce a whole lot floundering crew of four Cuban to sneak aboard the Dauntless. At of Spanish stomachache with its landlubbers, the boat drifted out night in a fog, he got her underway, pills.” Because the after deck was of sight into Hawk Channel. and escaped the revenue cutter crowded with the small boats, the Powerless to aid Mike, the men on watch. He was, at that moment, gun could not be located there. the beach gave the boat up for lost. on his way to No Name Key to Mike, assisted by Ralph Paine and But at noon the next day, much to rescue the expedition. Paine and an engine crewman, set the gun up everyone’s surprise, a small boat, his companion decided they had on the forward deck next to the deck with a tiny patch of cloth bellying better get back to No Name in a house. He shouted to the pilot house, out from an upright oar, sailed hurry. Paine managed to persuade “Ready to fire!” and to the Spanish slowly into the beach. Taking the skipper of a fast steam yacht, gunboat, now less than a half mile advantage of a favorable shift in the the Vamoose, under charter to his astern, “Prepare for burials at sea!” wind, the indefatigable Mike Walsh newspaper, to take them back to No O’Brien swung the tug so the gun had jury rigged his shirt as a sail. Name Key. would bear. Expecting to hear the Mike roared “I’ve been to the coast A fleet of ten local sailing craft report of the gun firing, all he heard of Africy and back with a crew that had been hired to expedite taking was curses from the gun crew. Walsh made me weep continuous. An’ me the Cuban expedition personnel and fixed the problem and reported he only shirt is blown out of the bolt arms back aboard Dauntless when was ready again. On the second ropes for I couldn’t stop to reef it she arrived. The operation was in attempt, the gun fired and the shell after I got it set.” full swing when Vamoose appeared hit the Spaniard’s forward deck During the next four days, a heavy over the horizon headed for the house and exploded, completely norther blew, and the party’s food scene at full speed. Thinking they destroying the deck house and the and water were almost exhausted. had been discovered by a revenue pilot house. The stricken gunboat When the weather calmed, Mike cutter, the skippers of the sail

8 - FLORIDA KEYS SEA HERITAGE JOURNAL - FALL 2014 The Dauntless and the Three Friends. Photo credit: The Author.

boats turned and ran for the narrow to one battleship, six cruisers, five news of the sinking of the Maine channels between the Keys. At the gunboats, and six revenue cutters. in Havana harbor and realized that urging of the skipper, the black On two occasions, one because of their adventure-filled filibustering gang on Dauntless began stoking a boiler explosion on Dauntless, days were coming to an end. the boiler fires furiously. she was intercepted and brought Before Dauntless could slip her into Key West and charged with SOURCES cable, Vamoose was close enough violation of neutrality orders. In Horace Smith. A Captain to be recognized as a yacht and not both cases because of insufficient Unafraid: The Strange Adventures a revenue cutter. While Ralph Paine incriminating evidence or testimony of Dynamite Johnny 0‘Brien. received a torrent of oaths from and the pro-Cuban-revolution Harper & Brothers, New York and a Cuban general for upsetting the sympathies of local officials and London 1912. loading operations, the sailing craft jurors, she was released. Paine, Ralph D. Roads of were recalled. It was late afternoon Returning from her last run in Adventure. Houghton Mifflin Co., before all the arms and men were February 1898, Dauntless paused 1925 aboard Dauntless. Three days later, briefly at Bahia Honda to drop off Proctor, Samuel. Napoleon O’Brien landed them successfully O’Brien and several Cuban officers. Bonaparte Broward: Florida’s in Cuba With the help of local spongers and Fighting Democrat. University Dauntless made four more fishermen and Cuban leaders in Key Press of Florida, 1950. runs to Cuba in 1887 and one West, O’Brien was able to arrange more in 1898. During the course for the passenger sidewheeler City John Viele is a retired naval of these operations, O’Brien once of Key West to divert from her officer, former submarine again played hide and seek in the regular run to Biscayne Bay to commanding officer, author of a Keys with the Navy’s blockading pick up his party. When they were three-volume history of the Florida forces which had been increased on board, they received their first Keys, where he now resides.

FALL 2014 - FLORIDA KEYS SEA HERITAGE JOURNAL - 9 Sergeant Calvin Shedd at Fort Jefferson Calvin Shedd was a carpenter heartily. I was on guard and it helps at home, but we sweat three time turned soldier from Enfield, New me to keep awake; as I looked on the as much. I hope Cummings will do Hampshire who served in the stars. I thought perhaps you might what is right by you but I expect from 1861-63. As a be looking at the same & it was a he will come up with some money. first sergeant and later a second happiness to me to think that we He is a slippery fellow on a trade. lieutenant with the 7th New were looking at the same & it seemed Lieutenant Williams thinks he will Hampshire Volunteer Regiment, to be a bond of sympathy and love. I start for home soon as he thinks his Shedd witnessed first-hand the am in good health and spirits but papers will be signed this time as hardships of a soldier’s life at Fort on “Police” & we have to load gun he got Dr. Brown to endorse them. Jefferson during the Civil War. carriages this p.m. I have no time Don’t speak of that, however, as Arriving in the Tortugas in March, to write only from 12 to 1 & eat my perhaps he would not like to have it 1862, Shedd’s unit departed less dinner out of that so you must excuse known. He tells me things he don’t than four months later. During that me as the mail goes out at 5 p.m. and tell everybody. There are no signs time, Shedd and his fellow New I shall not be off duty till that hour. of pay day yet. I am afraid we shall Englanders experienced unbearable I am very sorry to hear that Johnson get none until July, although there heat, mosquitoes, sickness, is no more for he was a man of good are stories that it is coming every boredom, poor food, overcrowding, heart. I liked him. Peace to his ashes. week. Dodge has got a 24 pound and death from disease. The One o’clock is now beating. I will try ball attached to his ankle with a following letters were written to write some more if I can run away chain stout enough for a horse to by Shedd to his wife, S. Augusta from duty a few minutes this p.m. draw by; he has got to wear it two Shedd, and three daughters living in May 28th. I thought I should get months. He looks rather sober over New Hampshire. These letters begin time to finish this the other day but, it. Sam is pretty well – a little lame when he left New York for Fort could not get a minute. I was quite at times. Burrell is well, sends his Jefferson. (This transcript makes sick yesterday. I hurt my back lifting love to his little girl and friends. All changes in Shedd’s punctuation and gun carriages and took some cold. I of my boys are well as usual & the spelling to improve the readability feel better today. We have had spring best squad in the Company. They without changing the meaning). showers here for a day or two. It will have gained some on the Fort: since Upon leaving Florida, the 7th New rain vary fast for a few minutes, then we came they are now building the Hampshire Volunteers were sent to the sun comes out hot again. I don’t magazines on the parapet. Bricks the coast of . The know what to write: there is no news arrive here in large quantities: they regiment, however, was plagued going. There has several vessels cost the Government $17.00 per M with ill health and was ordered to arrived within a few days: a gun boat & come from Maine. They have St. Augustine to recuperate. Over yesterday, the Wanderer, of Slave got the new condenser at work and the next months, Shedd suffered Trade notoriety, but none of them it makes much better water than from chronic dysentery and spent with any news. There has been nearly we have had heretofore, it is very much of his time in the general 200 men detailed for several days to clear and tastes much better than hospital in Hilton Head. Unable to unload a cargo of coal & of shot & that made by the old one. It is near rejoin his unit and pronounced unfit shell. The vessel that brought the supper time; we eat at 5 & then get for active duty, Calvin Shedd was shot & shell has 80 men of Michigan ready for dress parade at 6. I want formally discharged from service and Vermont Regiments that were to see you all very much but it is on December 31, 1863. left behind sick and now go to Ship of no use longing but must wait the Island. They left this morning. I feel course of events. Fort Jefferson, May 25, 1862. very weak and nervous. I can hardly My Dear Wife Augusta, write it is so warm and muggy. I My Best Love to you all, have no energy. I shall be better in I am most happy to have the a day or two. P.M. I have just come C. Shedd, time to acknowledge receipt of a in from drill the sweat is running 4th Sergt. letter from you, Ada & Annah of down in streams. It does not seem Co C 7th Regt NH Vol. May 11th, for which I thank you much warmer than it is frequently That is a handle for a name.

10 - FLORIDA KEYS SEA HERITAGE JOURNAL - FALL 2014 Fort Taylor and Key West Harbor during the Civil War. Photo credit: Monroe County Library.

Fort Jefferson on heavy artillery. We fired 10 the gun. I could have cut Chase’s June 9th, 62, 3 PM. shells that cost Uncle Sam $100.00. heart out with a good relish. Captain I had command of Gun No 8, an Langdon ordered my detachment Dear Wife, old Chambered Columbiade. She away from the piece. I marched I hear that a mail leaves here this made the best shot. Corporal Chase them away & broke rank, feeling eve. I have nothing to write but will was my gunner, the battery under ashamed enough; but they could not send you a line, if it is not quite so command of Captain Langdon get along without me. House came bright. I am pretty well – in fact of the regulars. We commenced to me to take command of number quite as well as one could expect drilling going through the motions 8 & turned out Sergeant Noyes. in this climate. It is tremendous hot of loading & firing. We had been I made the best shot after all the here today. Two men died yesterday loading by detail & was ordered to fuss; then I felt some better. There one was sick only 13 hours, the load for action, i.e., to go through the was no damage done for we drew other had been sick before in the motions without direct commands the shell & cartridge and it was all hospital & was discharged from it a for every motion. I was instructing right. I have had no papers for the day or two ago. His orderly put him numbers 1 & 3 in relation to their last three mails: don’t send only the on fatigue; he said he was sick & not duties when my gunner ordered the latest ones up to the time of writing. able. The orderly told him he was men to load with cartridge & shell. There is no signs of a paymaster yet. not sick & if he did not go to work I did not find it out till I heard the I begin to think we shall not get any he would put him on guard. He went shell grating inside the gun as they pay till the middle of July, which to work a little while, then went to were ramming it down. You had shall be six months. A rather long the hospital & died in a few hours. better believe I swore, as it was my time to wait but I suppose it is sure The lives of many of us will lay at duty to cut the fuse & prepare the to come sometime. Burrell could not the doors of some of the officers, shell. There it was the shell in the stand it in the kitchen but a week. I the curses of the men against them gun without any fuse & if fired in don’t see how Ned stands it so well, are loud & deep. The inspector did that condition, liable to burst in the he is tough. Tonight we have got to not leave Saturday as we expected. gun – to burst the gun & knock us all go to dress parade. Earlier tonight to This morning Company C was into a Cocked Hat. There stood the show the Inspector our skill in firing paraded to show him our dexterity & inspector not 10 feet from (Continued on page 12)

FALL 2014 - FLORIDA KEYS SEA HERITAGE JOURNAL - 11 (Shedd from page 11) blank cartridges in a sham fight. If we are reported to General Hunter favorable, I presume we shall have to take the field this fall & leave our bones to bleach in the sun of Dixie: well, let her rip. It is appointed once to die, then cometh the Judgment, then we shall see what we shall see and I am of the opinion that many will be disappointed if there is a Hell. I expect to go to it & I don’t believe it is much hotter than Tortugas and if is I should rather keep away. Keep up good courage, be as happy as you can, don’t let anything in the future trouble you any more than possible.

I close with my love to you all,

C. Shedd. Fort Jefferson National Park today. Photo credit: Monroe County Library.

Fort Jefferson June 1st, 62. have the sore throat. House has done you doing there?” They give wrong some almighty mean tricks to which orders & snarl the men all up & can’t Dear Wife & Children, it will not answer to record. I will fix seem to learn. Appear frightened as It is Sunday morning we have them sooner or later if I live. a parcel of whipped boys when their just come in from inspection & it is 3d. It is cooler the wind blowing daddy is around. very hot. The boys were streaming quite hard & partially cloudy. I 5th. I remember yesterday with sweat. I am better than when should like to have you heard the & today as the birthdays of our I wrote last. There the Colonel & boys swear yesterday p.m. when we children. I have thought of you all staff has just passed through the came in from company drill. I never many times. Yesterday I went to quarters. The wind tipped over my saw such a numb head as House: West Key after shells, I got about a ink bottle & spilled the whole on it was one continued blunder all pint of all kinds. I shall try to send my rubber blanket which I use for through the drill. At one time he had them by Williams, if he ever goes a tablecloth. I don’t know as I can the company wrong end, too: inside home. You don’t know how hot it write much as each day is about out & he was on the wrong side of was on that barren sand yesterday: a pattern of the next – all nearly the company himself, the company it seemed as if the sun would alike & no news except a rumor was perfectly disgusted & ashamed burn into ones brain. I don’t wear that North Carolina has returned with & of him & of the appearance anything but my old fatigue cap. to the Union. If true you will have they made on the parade ground. Many have got thin hats but I am known it for a long time. It is The company will show him up if going to be a Soldier while I am in uncertain when a mail will leave they ever get home. Well it is no use the Army. I wear nothing but Army here; we expect one the middle of talking. The Colonel swears at the clothes except stockings. At noon the week. Williams is as tickled officers on drill night. I should think the sun is exactly in the Zenith: a as a boy at the prospect of going they would feel ashamed. He yelled pole placed on end perpendicular home. It will take him down a peg out to them the other day what in H- casts no shadow. It is rather odd to if he is disappointed this time. The -l are you about. You don’t know as see the sun shining on all sides of Regiment is in better health than at much as your men do. That suited the Lighthouse equally. It is sweat- any time since we arrived. A good the boys. He sung out at House the sweat day & night. No mail yet; we many have the rheumatism, some other day: “Damnation, what are expect one every day as soon as we

12 - FLORIDA KEYS SEA HERITAGE JOURNAL - FALL 2014 A ship captured running the blockade in Key West during the Civil War. Photo credit: Monroe County Library. good. Ned is well, works hard in the receive it there will be one leave so I packed & be inspected. We had a kitchen. Burrell is with him, he says write along from day to day. I think shower this morning so that it was Ned is trying to be pious. I have it is about the best thing you can do quite comfortable for this place. thought it was all moonshine, but to let Mr. Pillsby have the pasture We have an advantage in being Burrell thinks it is so. If so it is well. as you propose. Last night 7 of our the 2d company that is inspected That it is so also probably he will be boys went to Loggerhead & got two and get in sooner than the other 8 more so. turtles as big over as tables. One laid companies. I should have liked to 7th The Mail leaves at 6 p.m. 134 eggs after they turned her over. have seen Cambridge in the pond for Key West. I will try and fill This morning they butchered the better than any other man I know the rest of this sheet but I hardly other & took out 130 eggs, beside of. We hear that there has been a know what to write. We had a hard a half pail full of little eggs without requisition on Governor Berry for battalion drill this morning. The shells each turtle has 3 sizes in them: another regiment & the President colonel was showing us off to the one batch with shells ready to lay, is going to call out 100,000 more inspector. The sweat dropped on the others look like yolks of hens’ men. If that is the case you will the blouses like rain. Our shirts we eggs: they cannot be boiled so that not see us at home at present if could wring sweat out with ease & the whites will be hard as other eggs ever; for if we have to go to the all this before breakfast. We are to but have to be fried or poached. mainland & go through with one drill by companies in the course of June 6th. Yesterday p.m. we or two campaigns. Many of us will the day to see which is the best. It is are very happy in receiving a mail be under the sod within a year. So rumored that some of the companies yours of the 18th of May. I was prepare for the worst & hope for will have to leave. Company C very glad to hear that you were all the best is my motto. Williams will make a splendid appearance well. I did not think Ada would get has got no backbone more than an if House drills us. I hope he will. promoted so soon. I think she is eel: that is the greatest objection Williams expected to receive his pretty smart – don’t let her study to the men have to him. It looks as discharge by the last mail. I think hard. Annah must not be jealous of if the government thought the war he was much disappointed: he has her, for I hope she will get in with was not very near its close if this not had a letter from his folks for her when she is as old. The Inspector above rumor is true. We are going five mails for when he first resigned General of this Department arrived to have turtle soup for dinner today, with the mail & at 8 this morning if we could have things to season we had to go out with knapsacks & put with it probably it would be (Continued on page 14)

FALL 2014 - FLORIDA KEYS SEA HERITAGE JOURNAL - 13 (Shedd from page 13) he wrote them to stop till further orders. He has written about every mail: perhaps some of their letters have been miscarried. There was one man on guard a week ago last Thursday who was buried last Tuesday of Company I, and another of Company G. who was on guard Tuesday and buried Thursday. The men are dying this week fast of typhoid fever, congestion of lungs & sun stroke. The Surgeon ordered us in yesterday out of the sun. He does most every day but the officers take the men right out again the next day in the sun regardless of their lives & health. I hope God will forgive the officers for the men won’t. There is a number of cases of petty tyranny in the regiment just because the officers don’t know their duty. I want to see you very much if the war lasts three years it is hardly an even chance that I shall, Colonel Haldimand Sumner Putnam Commander 7th New Hampshire Volunteer so don’t worry about me anyhow Regiment. Photo credit: Monroe County Library. for I don’t believe it is much worse ago suddenly. We thought there was & keep you happy and contented, to be dead than to be alive. I am something in the wind. She sailed going to be just as little homesick as round west of Loggerhead & arrived C Shedd. possible and do my duty & let come just in time to see a steamer capture what will. I have a good reputation a schooner loaded with cotton Fort Jefferson June 14th, 1862. as a soldier in this regiment in spite bound for Havana that had run the of my enemies, they may do their blockade. Such is the report. The Dear Wife, worst. Wanderer arrived here last night I had the happiness of reading this & left this morning. She makes a EDUCATION PROGRAM C. Shedd. business of cruising in the Gulf for SPONSORS such vessels as run the blockade. I $100 OR MORE wish I knew how many shells you LINDA & LAWRENCE ABELE June 7th p.m. it is extremely TOM & KITTY CLEMENTS could use & give away profitably. If PRUDENCE CHURCHILL & LAWRENCE PLUMMER hot there are 8 teamsters of this BETTY L. DESBIENS I stay here long I could send a peck BUD DRETTMANN Regiment going to Key West at JOHN & BEATRICE DUKE if it was necessary & would pay. I SHIRLEY FREEMAN & HARVEY SERVER work on a railroad. They will have CELESTE ERICKSON want you to burn one sheet of the DR. ELIAS GERTH a hot job. I think we shall escape MARY HAFFENREFFER the drill today as it is so hot & the letter I sent you about a fortnight TOM & LYNDA HAMBRIGHT HARRIGAN FOUNDATIONS, INC. inspector leaves at six. There were ago. I have not had a spell since half JOHN H. JONES LAURA LYNNE KENNEDY five companies drilled this a.m. & so bad, in fact not to touch it, but if EDWARD B. KNIGHT TOM KNOWLES we come next. A boats crew from I live to get home remember what I TOM & BARBARA MARMION DR. WILLIAM R. PLOSS Company E went to Loggerhead wrote & be prepared for I shall be LARRY & GRETCHEN RACHLIN JUAN L. RIERA last night & got 4 Turtles. One of in great distress & it takes powerful JUDITH & JAMES ROBERTS SOUTHERNMOST HOTEL IN THE USA them the largest seen for a long time remedies for great diseases. ED SWIFT KIMBERLY & GARY WALWER it weighed 375-lbs. The gunboat Good Bye My Dear Girl. I return ROBERT J. WOLZ Wanderer left here about a week the wish that God will bless you all

14 - FLORIDA KEYS SEA HERITAGE JOURNAL - FALL 2014 morning yours of May 15th & June should not remember that my first 1st, also one for Mr. McConnell. He & last love were centered in you & wrote the first particulars of Enfield our children; that covers the whole BUSINESS MEMBERS politics that I have heard & I am ground except a remembrance of ALLEN COUNTY PUBLIC LIBRARY greatly obliged to him & will write all my friends. There is no regular GENEALOGY CENTER 900 LIBRARY PLAZA him as soon as I get time, which, mail leaves here till we leave but the FORT WAYNE, IN 46802 260-421-1223 before I get through, you will see is captain of the steamer that brought COASTAL SAILING ADVENTURE, INC. 28555 JOLLY ROGER DRIVE pretty well occupied. Our inspector the mail this morning will take LITTLE TORCH KEY, FL 33042-0839 295-8844

I wrote you about has gone to seed; letters to Key West in season for the CONCH TOUR TRAINS, INC. 601 DUVAL ST. we were reported to be in first rate mail that leaves for N. Y. tomorrow. KEY WEST, FL 33040 294-4142 condition in regard to clothing & If you receive this I think you had DR. FRED COVAN 1901 FOGARTY AVE. SUITE 2 equipment. The mail came in this better direct to Hilton Head S.C. or KEY WEST, FL 33040 305-294-7522 morning before I came off guard & perhaps if we should go elsewhere DEWOLF AND WOOD ANTIQUARIANS ON THE GREEN I am very sleepy. Now for the news you may get notice of it in the P.O. BOX 425 we received: the steamer Ericsson papers before I can write again. We ALFRED, MAINE 04002 207-490-5572 FRIENDS OF ISLAMORADA AREA STATE PARKS is ordered here to proceed to Key shall be 5 or 6 hundred miles nearer P.O. BOX 236 West & take on 2 or 3 companies home than here. I have contracted ISLAMORADA, FL 33036 of regulars there, then to proceed no very pleasant associations here & DR. ELIAS GERTH 2505 FLAGLER AVE. to Hilton Head, S. C. Hurrah bully consequently can leave with a light KEY WEST, FL 33040 305-295-6790 for that although we are going right heart: whether we get better or worse HISTORIC FLORIDA KEYS FOUNDATION 510 GREENE STREET away from home as far as comfort treatment we shall have change of KEY WEST, FL 33040 is concerned: although there is but scenes which will go far to make HISTORICAL PRESERVATION SOCIETY OF THE UPPER KEYS, INC. precious little of it here we shall men think lightly of the hardships P.O. BOX 2200 see service now, I think in the state we may be obliged to bear. I have all KEY LARGO, FL 33037 KEY WEST ENGINE SERVICE, INC. I have always wanted to be in as all my courage left & I hope you will P.O. BOX 2521 true Mass Men have a particular never have cause to blush for me KEY WEST, FL 33045 KEY WEST TENNIS grudge against the devils there. when the time of trial comes. Live 1305 REYNOLDS STREET Oh! If we only had good officers or Die I hope you & our children KEY WEST , FL 33040 561-445-7805 KEY WEST WOOD WORKS I should be much better satisfied will in thinking of me, feel proud in 6810 FRONT STREET STOCK ISLAND for in a fight we are liable to be the knowledge that I have done my KEY WEST, FL 33040 296-1811 MEL FISHER MARITIME HERITAGE SOCIETY murdered by their incapacity. I duty. We expect to go Tuesday in the 200 GREENE ST. expect it will be a long time before mean time we have to load all of our KEY WEST, FL 33040 294-2633 OLD TOWN TROLLEY I hear from you again if ever. Life camp equipage & provisions which 6631 MALONEY AVENUE is very uncertain here at the best; will be quite a job. We shall have KEY WEST, FL 33040 296-6688 strong men are taken sick & in two PIGEON KEY FOUNDATION to leave many things here which P.O. BOX 500130 or three days are put in the sand. we cannot carry. I am disappointed MARATHON, FL 33050 Someone dies most every day. They in not being able to send the shells RIERA TOURS P.O. BOX 522026 die in the forenoon & are buried in I have gathered I don’t know what MIAMI, FL 33152 305-446-2712 [email protected] the afternoon in a pine coffin just I shall do with them. Well it is no A.R. SAVAGE & SONS, INC. planed enough to take the slivers use of thinking of carrying them as 701 HARBOUR POST DRIVE TAMPA, FL 33602 813-247-4550 off. Then they wind the Stars & I have got to through away some of SEASTORY PRESS Stripes around them and put them my clothing for I cannot get it all 305 WHITEHEAD STREET #1 KEY WEST, FL 33040 296-5762 in a boat, fire a volley & tote them into my knapsack. [email protected] over to Bird Key bury them about SOUTHERNMOST HOTEL IN THE USA 1319 DUVAL STREET two feet deep in the sand & we Adieu Dear Ones; I cannot stop to KEY WEST, FL 33040 296-6577 forget them as soon as they are out write more today, ST. LOUIS AUTOMATIC SPRINKLER CO. 3928 CLAYTON AVE. of sight. The Army is the death of ST. LOUIS, MO 63110 314-533-7710 all human feelings I feel that the C. Shedd. DONALD E. YATES, P.A. LAW OFFICE 611 EATON STREET chances are that I may never see KEY WEST, FL 33040. 305-296-2261 N.H. again but I am not going to This is Calvin Shedd’s last letter worry about it. I most earnestly from Fort Jefferson. hope that you will not all is if I

FALL 2014 - FLORIDA KEYS SEA HERITAGE JOURNAL - 15 Fort Jefferson C 1930. Photo credit: Monroe County Library.

Key West Maritime Historical Society NONPROFIT ORG. P.O. Box 695 U.S. POSTAGE Key West, FL 33041 PAID KEY WEST, FL PERMIT NO. 30

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