Darmody recruits Winslow to help in a hijacking to take place in January 17, 1920. Darmody has Winslow drive him into Hammonton, New Jersey with Al Capone. They overturn Winslow's car to block the road and Winslow lies in the road to suggest an accident took place. When a convoy of trucks transporting alcohol belonging to New York organised crime boss Arnold Rothstein comes upon the scene Darmody and Capone wait until the convoy's guards are attempting to turn the car back onto its wheels and then ambush the men. Darmody instructs Winslow to collect the guard's weapons.
The hijacking goes awry when Capone is startled by a deer. Capone and Darmody open fire on Rothstein's men, killing several of them. Capone and Darmody track the survivor's into the woods and kill them too. Darmody sends Winslow back to town while he and Capone drive the trucks off. ("Boardwalk Empire")
Winslow is arrested five months later in Tom's River, New Jersey for the armed robbery of a jewellery store. Terrified of going to jail and leaving his sick mother alone, he offers to reveal what he knows about the Hammonton hijacking and is put in touch with Prohibition Agent Nelson Van Alden to negotiate a deal. Winslow tells Van Alden that he was a decoy in the "Woods Massacre" of January but that he didn't kill anyone since nobody was supposed to get hurt - it was all the work of Jimmy Darmody "and this other fella, Al". Van Alden is delighted by this information but refuses to promise anything beyond the fact that he will use the best of his influence if Winslow agrees to testify. Winslow is then moved to the Atlantic County Jail. ("Home")
Jimmy is arrested eventually in mid-July 1920. During interrogation he claims to know nothing and that he was at the movies then, taunting Van Alden with the fact that he has nothing on him. Van Alden has then Jimmy moved to a cell while Winslow is moved to another, they meet and their masquerade falls as they scream at the other trying to know what he has told to the feds. Convinced that Winslow is going to testify against him, Jimmy calls Nucky Thompson and asks for help, to which he answers that the solution to this problem is not in the legal system. Although he doesn't say it, he has bought Agent Sebso, Van Alden's partner, to take care of it.
Sebso proposes Van Alden to move Winslow to a federal prison in New York City where Nucky Thompson's arm will not reach him. Van Alden agrees and Sebso departs with Winslow in a car. However, upon leaving Atlantic City Sebso stops claiming that he has to urinate and lets Winslow get out to stretch his legs. Sebso then shoots Winslow in the chest, injures himself with a rock to pretend that he was attacked and takes Winslow's body back to Atlantic City - the case against Jimmy Darmody forever ruined. ("Belle Femme")
- Jimmy Darmody: Associate and partner in crime (deceased)
- Al Capone: Partner in crime
- Eric Sebso: Murderer (deceased)
|Season one appearances|
|Boardwalk Empire||The Ivory Tower||Broadway Limited||Anastasia|
|Nights in Ballygran||Family Limitation||Home||Hold Me in Paradise|
|Belle Femme||The Emerald City||Paris Green||A Return to Normalcy|