By Terrence McCoy
By Scott Fishman
By Deirdra Funcheon
By Allie Conti
By New Times Staff
By Ryan Pfeffer
By Deirdra Funcheon
By Kyle Swenson
His next artificial daddy was a Chicago mobster.
Caulfield dropped out of school at age 15 and ran away to Las Vegas at 17. Then he got a call from his old girlfriend. She was pregnant in Chicago. He didn't really want to, but he returned and married her. At 18, he was a married father. (He's now 39 and a grandfather.)
At age 21 he was training police dogs and doing some security work in Indiana, across the Illinois border. Then a mobster named Phil (his last name, at Caulfield's request, won't be printed in this article) bought an attack dog from Caulfield. Impressed with the kid, Phil offered him a job.
The new gig was running a pornographic bookstore, which came complete with coin-operated peepshow booths. It was in the same building as a "health spa," which he says was actually a whorehouse. He claims he had nothing to do with the whorehouse, though he knew Phil owned it. "I wasn't a prude," he explains.
Part of his job was driving the bookstore proceeds to Phil. Caulfield established his honesty, so Phil bought him a used van and some furniture and helped him get into a house. He even gave his bagman a proper nickname: "Dog Boy."
For a young man with a wife and two kids to support, the job was a godsend. Caulfield says he was convinced that Phil and his men weren't real mobsters, just "wannabes."
His mother, when she heard where her son was working, had no illusion. "I told him the Mob was probably involved," she recalls. "But he said, 'Oh no, he loves me. He's like a father to me.'"
Soon enough Caulfield started feeling uncomfortable, and Phil started noticing that Dog Boy was getting skittish. The mobster made it clear that his employee wasn't going nowhere. He showed Caulfield a ledger of all the things he'd bought for him -- plus the interest, of course. Phil set the total bill at about $7000. It'd have to be paid, or else.
"I'm not having much fun now," Caulfield says of that day. It went downhill from there.
Caulfield left in the van Phil gave him. After hearing some threats, Caulfield says he took the offensive, or what he terms "preemptive self-defense." Others might call it a death wish. He called Phil and told him he'd better watch his back, "because I might walk up behind you and, kapow, blow your brains all over the street."
"That's a pretty good twist isn't it?" Caulfield says, loving the concept. "Dog Boy kills Mob guy."
Caulfield went into hiding but resurfaced for another dose of aggressive self-defense. He says he got into Phil's house and killed both of the attack dogs he'd trained for him. The brutal act was the worst thing he's ever done in his life, he says, but he still feels it was necessary. Caulfield decided that the only way to save his own life was to put the fear of God into the mobster.
He laid low for several months until the day FBI agent Ivan G. Harris knocked on his door. Harris had been investigating the Mob, and Caulfield's name had come up. Harris questioned him, then told him he was free to go.
But they wanted him to give testimony about Phil's business and payoffs to dirty cops.
Caulfield agreed to do it.
Harris says Caulfield, with whom he still keeps in touch, earned his admiration back then and continues to earn it. He considers his willingness to testify heroic.
"He was a very young man at the time, and he was one of the many pawns [the Mob] was using," says Harris, now the organized-crime supervisor for the FBI's Chicago office. "I have a lot of respect for him. He did what he did at great risk to his own safety and made a tremendous sacrifice."
His mother got a call after Caulfield made his decision.
"Mom, I'm in trouble," Rose recalls him saying. "I'm going to the Witness Protection Program."
It isn't easy to erase a life. Caulfield and his family had to move to a federal safe house for a time, with all of their belongings put in storage. Caulfield, of course, lost his job. He and his family had to close all their accounts and find all the documents that had their real names on them -- including personal letters -- and give them to the federal government, never to see them again.
Uncle Sam was Caulfield's new daddy.
For Caulfield's mother, Rose, it was tragic. She was essentially losing her only son and her two precious grandchildren.
The first name her son chose for himself was "Jack Walsh." Shuttled from airport to airport, he had no idea where he would live until he got there. His first home was Roanoke, Virginia. He was given $3000 and a stipend of $1600 a month. He got a job with a security company, and his cover was blown. It's a complicated story. He blamed the marshals and the marshals blamed him. Bottom line: He wasn't going to be Jack Walsh any more.