He enjoyed the game of golf, as did his partners in crime, Tommy Holden and Francis Keating. This lead to his downfall.
On July 8, 1932 in Kansas City at the Mission Hill Golf Club, Harvey, Holden, Keating and Fred Barker were getting ready for a round of golf, waiting on their friend Bernard Phillips to appear. Bailey was anxious to tee off and decided they should begin without Phillips. Barker who cared little for the game, declined and headed off in another direction while the group of three began their game.
When they approached a ditch on the course, eight officers appeared heavily armed. They knew who Holden and Keating were and one of the officers suggested letting Bailey go because they weren't looking for him. That idea was nixed and Harvey after being searched, a $500 liberty bond from the Fort Scott bank robbery was discovered, connecting him to this. It is thought that Bernard Phillips, who had arrived late, turned in his friends.
Holden and Keating were returned to Leavenworth, where they had escaped on Febuary 28, 1930 with the help of "Machine Gun" Kelly. Kelly, (real name George Barnes,) had worked in the Bertillion Room in the prison and had access to prison files, passes and such. He made the two fake passes and with the help of Frank Nash, some believe, civilian clothes were smuggled in. Holden and Keating simply walked out the front gate with the passes.
Bailey was tried and found guilty of the Fort Scott robbery and given 10 to 50 years at the Kansas State Prison.
Harvey seemed to accept his inprisonment, was positive he would live to be paroled and settled into the life of a convict. Wilbur "The Tri-State Terror" Underhill changed that for Bailey.
He enlisted Harvey's help with smuggling guns in and on June 1, 1933, he, Underhill, Bob Brady, Jim Clark, Ed Davis, Frank Sawyer and five others escaped the Kansas prison. Bailey saved the life of the Warden, Kirk Prathers, who they took hostage. Underhill hated the prison warden and wanted to kill him, Harvey refused to allow this to happen.
Bailey was shot in the kneecap during the escape and was bleeding badly. Prather's offered to take him to the hospital when he was released and seemed greatly concerned for Harvey.
When the Warden was released unharmed as Harvey had promised, he gave Prather's $5 for busfare home.
Prather's died of a heart attack in 1939.
Then the group headed for the Cookson Hills.
{Courtesy: John Dillinger Historical Society}
Warden Kirk Prather
Tommy Holding
Francis Keating
Wilbur Underhill
{Courtesy: John Dillinger Historical Society}
Underhill IO Poster
{Courtesy: John Dillinger Historical Society}
Jim Clark IO Poster
{Courtesy: John Dillinger Society}
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