In 1993 he enrolled at Central Carolina Technical College in Sumter, took a year and a half of industrial maintenance courses (hydraulics, valves, oil, electricity) and put in an application for a temporary job at A.O. Smith in McBee. Six months later he landed a permanent position at the company, wrapping insulation for the water heaters that came flying down the assembly line: six days a week, nine hours a day, $8.25 an hour.
"I went from being a good golfer to a weekend golfer with a job," Gainey says.
But even playing on the weekends, Gainey exhibited skills that were undeniable to those who came across him. In 1997 a friend offered to pay all but $100 of a $750 entry fee for Gainey to play in a Teardrop tour event in Columbia. Gainey paid the rest and won the darn thing.
"I won $15,000," Gainey says. "That opens your eyes."
Two Gloves spent most of his 20s bouncing around the mini-tours and competing in money games in the Carolinas. He quit A.O. Smith (only to return one more time for a three-month stint). He moved furniture. He became a cart attendant at Dunes West Golf Club in Mount Pleasant, living rent-free for three years in a hotel owned by a friend and burnishing his legend as a hustler.
"You see him with his swing and his two gloves, and he looks like the average guy," says Richard Rankin, the general manager at Dunes West. "So you say, 'Hey, how much you want to play for?' You're saying uncle on about the fifth hole."
In the big-money matches Gainey and other players would be backed by sponsors who would bet on them.
"We used to have some money games that could get up there," Gainey says. "I don't want to say any amounts, and I don't want to say no names." But he does say the amounts. "Some got up to almost 10 Gs a hole and half of that," Gainey adds. "The sponsors we had gave us a percentage. I don't want to say any more."
About six years ago, through a fellow player who was looking for an agent, Gainey was in a meeting with Paul Graham, a onetime manager of Hootie and the Blowfish, who was getting back into the agent business.
"Tommy was sitting there the whole time," Graham says. "I signed the other player and said, 'Tommy, what are you doing here?' He starts talking to me like I'm the money guy for one of his gambling matches. I said, 'Tommy, my goal is to protect you from guys like that.' And he said, 'Give me one of those papers. I'm going to sign with you too.'"