Pickles Leighton – Auld Irishtown
Pickles Leighton – Character in the Auld Irishtown trilogy
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Pickles Leighton won the War for the Inside and could provide many paroled soldiers to Lovett in the blood feud against Meehan.
“It’s all about the Leighton brothers. As long as Pickles sits in Sing Sing and Darby’s eighty-sixt, Lovett’ll never get wit’ us. Even after givin’ it to McGowen like they did.”
~The Swede
Pickles Leighton (b. 1889), also known as King of the Inside, is a murderer and prisoner in Sing Sing. He does not appear in the books, but is often spoken of. In 1900, he and his brother Darby Leighton were abandoned. By 1908, Pickles clashed with Dinny Meehan and joined upstart Wild Bill Lovett’s Jay Street gang. In a show of solidarity, Lovett allowed Pickles to go with Meehan to murder Christie Maroney in 1912. But Pickles was the only one convicted. Meehan grew concerned over controlling the inside of Sing Sing and the many convicts that could support an uprising against him, so he had his righthand McGowan plea guilty to a small charge in order to kill Pickles in Sing Sing. In the War for the Inside, many battles occurred that maimed Pickles, including losing an eye, but in the end Lovett paid a screw (prison guard) to beat McGowan to death. Now that Lovett has returned from the Great War alive, Pickles’ release could provide him a great many paroled soldiers in the gang war against Meehan and the White Hand.
Light of the Diddicoy
When Vincent Maher meets Liam Garrity in 1915, he brings him to McGowan’s Wake. Drunkard Mick Gilligan blurts that if no one has proven Lovett and Pickles are responsible for the murder of McGowan, then why is Darby Leighton banished to the shadows?
Exile on Bridge Street
In 1917, Dinny Meehan is shot and wounded by two recent parolees from Sing Sing. The Gas Drip Bard tells the story of the sensational trial for the murder of Christie Maroney where Pickles was incorrectly named the leader of the White Hand gang. In 1919, Italian Blackhander Frankie Yale tells a jailed Maher that he is the next man Meehan is planning to set up, just like what happened to Pickles.
