A New Gig for Sheffield

By Jason Beck
Updated: December 7, 2010

LAKE BUENA VISTA, Fla. — Gary Sheffield has found a new career counseling players on financial planning and contract negotiation, helping others do what he learned to do in the second half of his playing career. But he also hasn’t ruled out returning to what used to be his day job.

In a way, Sheffield was in his element on Tuesday, talking with reporters in the lobby of the Walt Disney World Swan & Dolphin Resort at baseball’s Winter Meetings.

He has there trying to gauge teams’ interest on players with whom he works. Among them are reliever Jason Grilli, who missed this past season with a leg injury.

But Sheffield also represents himself, and he isn’t calling himself retired just yet. He isn’t saying he was going to play in 2011, but he is open to it.

“[Teams] know who I am,” Sheffield said. “The thing is that hitting has never been my problem. I can still do that. I can still go out and hit 20-30 home runs.”

Sheffield, who turned 42 years old last month, last played with the Mets in 2009 after the Tigers released him in Spring Training. He joined the 500-homer club that year, batting .276 with 10 home runs and 43 RBIs over 312 plate appearances in his 22nd Major League season.

Sheffield said he had offers to play last season, but said he was holding out for a chance to play with his hometown Tampa Bay Rays, which never happened.

“I wanted to be a Ray, be at home,” he said. “I wanted to see what that was like. I talked to McGriff and he said, ‘Man, you ought to give it a shot and stay home.’ So I kind of held out until the last minute.”

That ship has now seemingly sailed, but Sheffield’s potential to play has not. He’s working out five days a week, he said, and feels he could play again if the right opportunity popped up. He has not talked with any teams as of Tuesday afternoon.

“If it doesn’t happen this year, I’m going to go ahead and call it quits,” he said.

It’s not as if Sheffield needs the money. He made $14 million as a player in 2009 and an estimated total of more than $168 million over his career, according to baseball-reference.com.

But he also established business interests during his playing career.

Sheffield made headlines a decade ago when he and agent Scott Boras parted ways. When he became a free agent after the 2003 season, he represented himself and signed a three-year, $39 million contract.

That deal led to a lawsuit from Boras and a case that went on for years before they settled two years ago. Sheffield’s most recent deal was a two-year extension from the Tigers once Detroit traded for him after the 2006 season.

Sheffield was always outspoken as a player, pointing criticism at everybody from Boras to umpires to opposing players at different points.

He’s still honest, but the topics are a little different.

Sheffield says he hopes to pass on some of the things he learned — not just about contracts, but about making playing money work for the future. He said his firm, Sheffield Management, works with about a half-dozen players so far. His goal isn’t to eliminate agents from the equation, he said, but to force them to do more.

“Guys laugh at me when I’m sitting them down in a meeting and kind of going over what I d,o and show them on the board every seven years, your money should double, and showing them my finances,” Sheffield said.

“I’m not hiding anything.

“And I lived with my mom until I was 30. So that gets them tickled.”