Raymond Hamilton’s Big Brother Breaks Out Of Alcatraz

A Texas outlaw finally stepped out of his dead brother’s shadow with a daring daylight escape from Alcatraz on April, 14, 1943.  Floyd Hamilton was relegated to a supporting role in the crime drama starring Clyde Barrow, Bonnie Parker and his younger brother Raymond.  Since his was the only face not regularly plastered across the front page, he purchased supplies, rented hideouts and coordinated prison breaks without attracting undue attention from the authorities.

    A Texas outlaw finally stepped out of his dead brother’s shadow with a daring daylight escape from Alcatraz on April, 14, 1943.

    Floyd Hamilton was relegated to a supporting role in the crime drama starring Clyde Barrow, Bonnie Parker and his younger brother Raymond.  Since his was the only face not regularly plastered across the front page, he purchased supplies, rented hideouts and coordinated prison breaks without attracting undue attention from the authorities.

    It was Floyd, who engineered Raymond’s sensational escape in January 1934 from the Houston County state penitentiary where he was serving 263 years from murder and armed robbery.  The older Hamilton took care of everything from arranging for Bonnie and Clyde to be waiting with the getaway car to planting two pistols in the woods for his little brother and a convict accomplice.

    The bloody breakout bought Raymond just three months of freedom and put him on the waiting list for the electric chair.  Brandishing handguns supplied by a guard that Floyd probably bribed, six condemned killers fled the maximum-security confines of Death Row in July 1934.  The charter member of the Barrow Gang and two others successfully scaled the high wall and vanished in a hail of bullets.

    Raymond lay low until February 1935, when he teamed up with Floyd to lead lawmen on a wild five-state chase.  After sticking up a bank in East Texas, the bandits predictably took refuge in their old West Dallas neighborhood.  Surprised and surrounded by six detectives, they shot their way out of the trap with so much as a scratch.

    The fast-thinking fugitives drove south into unfamiliar territory to throw pursuers off their trail.  The Hamiltons replenished their private arsenal at a federal armory in Beaumont before doubling back to North Texas, where they had their pick of hiding places.

    But the boys nearly bought the farm in a blazing gunbattle outside McKinney.  Fearing they would wind up like Bonnie and Clyde, cut to pieces by a shoot-first posse, Raymond insisted upon parting company.  That was the least he could do for the devoted brother, who had done him so many dangerous favors.

    Raymond was captured on April 5, 1935 and rushed in chains to Huntsville.  To eliminate the possibility of another embarrassing escape, the 22 year old desperado made the fatal acquaintance of “Old Sparky” 35 days later.

    Floyd was in Leavenworth doing token time for aiding and abetting, when word came of the execution.  He could have turned over a new law-abiding leaf but chose instead to follow in Raymond’s footsteps.

    Facing certain conviction on a bank robbery charge, Floyd pleaded guilty hoping to receive a single-digit sentence.  However, the judge rejected leniency for the career criminal and shipped him off to escape-proof Alcatraz for 30 years.

    On that April morning in 1943, Floyd was working in the mat shop with Freddie Hunter, an associate of the notorious Alvin “Creepy” Karpis, and fellow bank robbers James Boarman and Harold Brest.  The four overpowered the single guard, jumped the captain on his rounds and bound and gagged them before proceeding with their plan.
    To save time the inmates already had sawed the bars in two on the outside window.  It took mere seconds to remove the metal rods and slide through the opening a plank long enough to reach the perimeter fence.

    Floyd went first crawling on his hands and knees to the fence, where he dropped to the ground and started a cautious descent down the steep cliff.  One by one his companions followed until the group reassembled at the edge of the ice-cold water.  They stripped to their underwear, smeared grease on their bodies for insulation and began the long swim across San Francisco Bay.

    By this time the captain had worked his gag loose, but his shouts could not be heard over the noise of the saw in the woodshop.  But he did manage to sound the alarm with a whistle he plucked with his teeth from the guard’s pocket.

    The marksman in the roof tower spotted the four escapees and opened fire in accordance with Alcatraz’s unwritten shoot-to-kill policy.  Brest was hit in the elbow, and Boarman died instantly from a bullet through the head.  The wounded convict treaded water until hauled aboard a launch, but the dead body of his comrade sank beneath the waves never to be recovered.

    Hamilton and Hunter swam underwater back to The Rock and took cover in a cave.  Guards flushed out Hunter a few hours later but did not think to look under a pile of debris, where the fourth prisoner was playing possum.

    Floyd Hamilton spent two wretched days and three miserable nights waiting to be caught, but search parties never reexamined the cave.  Half-starved, dehydrated and bleeding from hundreds of cuts, the Lone Star outlaw retraced his escape route to the mat shop, where a startled guard found him fast asleep the next morning.

   Bartee Haile welcomes your comments, questions and suggestions at haile@pdq.net or P.O. Box 152, Friendswood, TX 77549.  And come on by www.twith.com for a visit!