Could the "Battle of Alcatraz" escape have worked if the prisoners had gotten the key to the yard?

So the plan for the escape was

  1. Use a bar spreader to gain access to one of the gun galleries
  2. Overpower the gun gallery guard, seize his rifle, and then capture and lock up the cellhouse guards
  3. Obtain the key to gain access to the yard from the cellhouse.
  4. Use the rifle to snipe the yard tower guards
  5. Take hostages, probably civilian workers or the warden’s family and commandeer the boat to take them and the hostages to San Francisco.

Obviously things went south when #3 didn’t happen because a guard happened to not put the key back where it belonged. It ended with the prisoners shooting the captive guards to eliminate witnesses, a full out assault on the cellhouse with heavy guns and grenades ending up with the three leaders killed, and two of the three accomplices were eventually executed.

But assuming they had gotten the key, could the rest of the plan have worked or was it wishful, desperate thinking?

Interesting difference in the Wikipedia account and the Alcatraz history page:

I actually just visited Alcatraz a couple weekends ago. The account there both mentioned that what he did was against the rules but was still considered heroic.

I don’t think (4) and (5) were ever viable possibilities.

In a conventional prison (especially in an urban area) it might’ve worked, but marooned on an island it was a hopeless proposition.

The families of the guards and other prison officials lived on the island. You would have had plenty of hostages.

But the boat off the island would have been a problem. I doubt any of the prisoners knew how to run it, so you needed to get the pilot to cooperate. Also, if word got out to the mainland, the cops would know exactly where you were and where you had to go to dock. You’d quickly be surrounded.

Yes, the boat would have been a real problem.

Once word of the attempt got out, I can’t imagine higher authorities allowing the boat to travel out to Alcatraz Island in the first place. Even if there were hostages.

Then there’s the problem mentioned before: they will be shadowing the boat, and have squads of police waiting at any dock where they land. Assuming they don’t just sink the boat on the way to land.

Might have been better planning to have done this when the boat was already docked at Alcatraz (though it would probably leave as soon as the alarm went off). Or possibly have some confederates on shore with a small boat that they could bring to the island dock on some signal. Though the same problem still exists: the authorities could easily track (& attack) that boat.

But criminals generally aren’t known for being smart.

Longtime Alcatraz volunteer here. They still would have had to eliminate the tower guards. In 1946 there were manned towers on the cellhouse roof, the roof of the Model Industries building, the west road, and the dock. Depending on time of day the hill tower may have also been manned. Coy shot at two towers and failed to incapacitate the guards, though they played dead. Had the inmates made it to the rec yard, they may very well have been sitting ducks.

The plan’s success relied on avoiding gunfire from the towers. Also, the key to the boat was kept in the dock tower and sent down on a chord. They would have had to force the guard in the dock tower to surrender the key. As far as taking additional hostages, the escape happened during school hours so there were no children on the island. There were some wives and I suppose taking them hostage was a possibility. But the plan was a longshot from the beginning. The moment the escape siren went off the entire island was running with armed guards, the Coast Guard was alerted, and all the surrounding police departments were watching the shores.

In generally thought among Alcatraz historians that the plan had almost no chance for success, though Coy exploiting the security weaknesses and getting into the gun gallery is regarded as incredibly clever.

Sounds like maybe in hindsight Miller should have just given them the key so the tower guards could have picked them off rather than having the guards all trapped inside with the sure to get desperate inmates?

The souvenir book I bought on Alcatraz suggests the key was hidden in or behind the toilet, where it was eventually found by the inmates but after they had jammed the lock by trying other keys.

It’s possible that that’s jailhouse lore. It’s actually not clear if it was hidden in the toilet or behind the folding medal chair against the wall of the cell. Yes, the rioters destroyed the lock by forcing the wrong keys into it.