TAMPA, Fla. -- Two months ago, Gary Sheffield -- the 43-year-old and still-musclebound former Brewers, Padres, Marlins, Dodgers, Braves, Yankees, Tigers and Mets outfielder who waggled his bat, hit .292/.393/.514 with 509 home runs, terrified opposing pitchers, and made writers' careers -- apologized to his old Little League coach, who once threw him off the team. They were naming a ballpark after Sheffield in Belmont Heights, his old Tampa neighborhood, and he was invited to the ceremony.
Sheffield still lives in Tampa, but his house is in Harbour Island, a gated community where chocolate-milk-colored stucco structures sit close together, with rock gardens, SUVs and palm trees in front, pools and water views in the back. Norman Schwarzkopf lives a few houses down.
When Sheffield was 11, he skipped a summer practice for the Belmont Heights League All-Stars, who were fresh off a Little League World Series loss to Taiwan. Instead he went to watch his uncle, Dwight Gooden, pitch across town. Gooden, who was 15 at the time, dominated his opponents and hit a home run, and Sheffield was glad he didn't miss it. By the time he got back home, his coach had already asked his parents why he had skipped practice. When he got to the ballpark for the next day's game -- especially excited because he was facing his rival, Derek Bell, and had a repeat of Gooden's performance in mind -- the coach told him he wasn't playing. Sheffield grabbed a bat and brandished it at his coach. Some accounts of the afternoon say that Sheffield chased him around the field. Regardless, he was kicked off the team.
According to Sheffield, this moment, and the ensuing summer of watching from the bleachers as his cousins and neighbors played ball, made him who he was. How did it change him?
"Rage started building up in me. Anger, rage and resentment. … I knew I was the best player on the team, and I should have gotten another opportunity, which he didn't give me." When Sheffield tried to join the West Tampa squad, where Tino Martinez, Luis Gonzalez and Fred McGriff played, the coach blocked him there, too.
He came back to Belmont Heights the next year, and the team again lost to Taiwan. But he had changed. He was now the resolute, angry Gary Sheffield that would play 22 years of major-league baseball.
When Sheffield said he apologized to his old coach, he didn't bring it up to convey that he had softened with age. His point was that he thrives through retaining idle rage for a long, long time.
* * *
I visit Sheffield in Tampa on a Thursday in late September. We're now driving in his flan-toned Bentley. The topic is how the press covered Sheffield when he played. He doesn't think highly of the media.
"The only thing the media's there to do is to let guys build images so they can make their off-field money," he says.
Gary Sheffield is an MLB player agent now, representing one major leaguer -- Jason Grilli, the Pirates relief pitcher -- and a handful of minor leaguers. He founded his company, Sheffield Management Group, in 2011 with his wife, DeLeon, and Xavier James, his attorney and a former bigwig for HBO Boxing.
The agency's stated mission is to prepare athletes for life after professional sports by setting them up with the proper investments and legal advice. Its real mission is to let Gary Sheffield negotiate with MLB's general managers. He calls up front offices and plays bad cop, while James plays good cop. ("I'm very bad-cop," Sheffield says.) Sheffield will say, I know the game, and I know for sure that my client is better than this guy, this guy and this guy you have on your roster. So sign him.
"I have not been wrong once," Sheffield says.
The agency doesn't consume too much of Sheffield's time. He takes calls from the players when they want to hear from him, and if a minor leaguer is struggling in the Tampa area, he'll pay a visit. Since the group is so small, he doesn't have to handle much day-to-day stuff. He says, "I've got people on the run, making things happen."
Sheffield is more or less the Cincinnatus of player representation: He didn't ask to do it, but they beckoned him. Players just wanted Gary Sheffield on their side. So he got his license, just in case he decided to get involved in the business. And then Jason Grilli called in 2010. Sheffield and Grilli had played together in Detroit and gotten along well. Grilli was out of the big leagues, coming off a knee injury, and he wanted back in.
"I didn't really want to put my name on the line, but me knowing Jason Grilli, I said I'd be on his side," Sheffield says. "You put Jason Grilli in a meaningful game, he's a horse."
Players who have been out of the game for a bit, players looking for spring training invites -- they call Sheffield. "I got a guy a job at Baltimore Orioles training camp by noon after I showed up there at 11 o'clock," Sheffield said. He wouldn't say who the player was, because they never formalized the agent-client relationship. But evidence suggests that it likely was hybrid knuckleballer Josh Banks, who did, in fact, land a minor-league deal with the O's after Sheffield made his case.
You could watch the sales pitch play out in real time on MASN’s Orioles blog. Sheffield rolls up in the Bentley, talks to Dan Duquette, and shortly thereafter, his guy's got a job.
* * *
Gary Sheffield says he is chiefly a dad now. When he says this, he is talking about his three young sons at home: Jaden, 10; Noah, 6; and Christian, 4. He takes them to school some mornings, and is always home no later than an hour after school gets out. If they have practices, he'll take them; otherwise, he’s there to make sure they do their homework. (Jaden plays baseball and football, and while Sheffield doesn't coach baseball, he does help out with the football team. During one recent game, a "pissed-off" 7-year-old asked why he wasn't in on defense. Sheffield told him that he had to learn how to be a good teammate, and kept him on the sidelines.)
"We just stopped our kids from playing video games and watching TV during the week," Sheffield says, with the affect of a man who has put a lot of work into this victory. "That's the only requirement I demand from my wife and my nannies and my assistants, to make sure my kids are the most educated kids out there." Jaden is taking gifted classes in school. Sheffield says he's "smarter than all the rest of us combined."
"It seems that way with all my boys," he says, which is a reminder that Sheffield has four kids (two sons) by four women he met before he married DeLeon. His other sons, Gary Jr. and Garrett, who were raised by their mothers away from Tampa, haven't caused him a lot of pain, but his two daughters -- Carissa and Ebony, who were born to two different local women when he was 18 -- have.
"These are my babies, but they're misguided. Part of it was their mothers. If I would tell them they need to go to college, their mothers would say, 'Well, college isn't for everyone.' Listen, if you're a young lady, you need to go to college. That's the only way you'll get paid without taking your clothes off. What job is there that pays you if you don't go to college? Men have sports."
So Sheffield sent both off to the Delphian School, a Scientology-affiliated K-12 boarding school in northwest Oregon. (Sheffield is not a Scientologist, but a born-again Christian. When he enrolled his girls, he told administrators not to teach them anything about Scientology.) Sheffield visited occasionally, and admired the education. Both Ebony and Carissa were set to enroll in college -- Ebony at North Carolina, and Carissa at UCLA -- which made Gary happy. But he says both gave up on college in the same week, before he and the Yankees were to face the Red Sox in the 2004 ALCS. He says he was tempted to leave the team to talk the girls out of it.
Both girls spoke to the New York Post about a month later, saying that Gary had forgotten about them since marrying DeLeon, and that they had been cut off. “Forgotten? No. But I cracked the whip,” Sheffield says. The way he tells it, he was happily supporting them through boarding school. He arranged for the girls to meet LeBron, Shaq and Kobe when they’d roll into town to play the Blazers. But when the girls dropped out of college, that was it.
"I told them they lost the $4 million I left each of them. I pulled up their accounts on the computer, and then I pulled up my account, and I hit transfer, and then I showed them their accounts with zero balance. And I said, 'Thanks, you just made me eight million dollars.'"
Sheffield says he took away the money because they had proved that they couldn't make good decisions. "If I put $4 million in your hands, and you don't have any judgment, I'm going to kill you. The money will kill you," he says.
Today, each girl's name turns up in multiple Tampa mugshots, along with a list of various charges they've faced. Gary says he's on good terms with them, and that he bought each a condo and a car, but that they're still deluded. "My daughters, they don't want jobs. They say they're overqualified for everything. I say, you're not overqualified if you don't have a job and you didn't go to college."
* * *
Aside from his family life, Sheffield is a dabbler. First among his business pursuits is his cigar line, the Rocky Patel HR500, which launched earlier this summer. "I sold 2,690 boxes in the first week," Sheffield says. "They didn't think I could do that." He has to appear at every store that purchases 75 boxes of cigars, at 240 dollars a box, so he plans on making more than 40 appearances, all over the country, for the cigars this year.
He's proud of his cigar, he said over lunch: "You know whatever I do, it's gonna be good, because I have a lot of critics. When you have a lot of critics, you can't just put anything out there. I can put my cigar with any cigar, and know that it's gonna stand to time. It's a Nicaragua blend, has a chocolate-nut flavor, and a Nicaragua wrapper. It's by Rocky Patel. ... When I get a cigar, it's a sense of relaxation, a sense of achievement. I make sure my kids are in bed, I go tuck 'em in, and have a cigar."
He's also thinking of opening a cigar bar. During our interview, he brought me into Lit, a cigar lounge in a Channelside strip mall, next to a Hooters.
"This is something I wanna do, but on a bigger scale," Sheffield says. Lit features one moderate-sized room and an adjoining humidor, with a few TVs turned to ESPN, monochrome posters of naked women, and 16 bottles of Grey Goose standing on a mantel. It is everything you'd ever dream a cigar bar in a Tampa strip mall would be. Sheffield lit up a Rocky Patel Freedom, a new cigar he got at a show. He had been carrying around a plastic bag full of sample cigars and cigar tools -- a hole-borer and a silver torch that shoots four prongs of blue flame. When he puffed through, the stogie produced the smoke of a small rubber fire.
Sheffield thinks he might enter broadcasting soon. He did some radio for a sports-talk station in Tampa, and a few shows on the MLB Network, and he got good feedback. He says that ESPN wanted him to come to Bristol, but he said no -- too far. The local station wanted him to come work full-time for them, but they had moved the studios to St. Petersburg, across the bridge. Also too far, he said. He shot a television pilot in spring training with other ex-jocks for what he describes as a "Best Damn Sports Show-type deal," and he says some networks are interested. Sheffield says he'd move for work if he could land a gig like Charles Barkley's or Michael Strahan's. He has opinions, and he'd like to share them on television. He's not going to get on Twitter, though: "I don't like when people think I'm boisterous about everything. Most things I just don't care about."
What else does he do? He owns a beach resort. His business partner, Xavier James, tells me that Sheffield also has a deal with "a Vitamin Water-type company." Sheffield says, "I'm thinking about buying -- well, I can't tell you -- it has to be approved with a big organization. I'm about to buy that." He skis, too. He has a house in Aspen, which he bought after a vacation there with his mentor, Dave Winfield. "Dave introduced me and my family to skiing," he says. "It's the best thing that's ever happened to us."
And he does whatever there is to do in Tampa. He was curious, so he attended every night of the Republican National Convention in August. He liked the atmosphere of the convention, but didn't care for how few black faces were in the audience. He didn't like Clint Eastwood's speech, either. He sympathizes with Mitt Romney, though, because both men are oppressed by capital gains taxes on overseas profits. He says, "If you're smart enough to make money out of the country, you shouldn't have to pay taxes on it. Mitt Romney would have done more here, created jobs, if the government let him."
Sheffield says his primary concern is with the plight of the working poor, and thinks the government should do more to help them. He's particularly troubled by what faces black men. Poor black men will never go to work, he explains, when the government lets women take half their income in child support payments. Then they get involved in crime, so the government doesn't see any income at all. "Change the laws, make the women responsible," he says. "Then they'll stop having all those kids."
Sheffield, a veteran of several paternity suits and child-support battles, knows that his position isn't a popular one. But, as usual, he doesn't care. "The thing is, I'm not really pro-this, pro-that, no. I'm pro-right."
* * *
The one thing that Sheffield doesn't really dabble in is baseball. "I pay baseball no attention. None. Not at all. I couldn't tell you one team's roster," he says. "I don't watch baseball now, because it's boring. When I played, I brought personality to the game. If it's strictly baseball, and you get no personalities, it's boring."
He likes three youngsters -- Mike Trout, Mark Trumbo and Bryce Harper -- and not too many other players. He thought the Stephen Strasburg shutdown was "a bunch of crap." ("Of course Scott Boras was involved," he says.) He knew Bartolo Colon was cheating the moment he heard that he went overseas for blood-spinning. He thinks pitchers who use Toradol injections between starts are also cheating. He doesn't take the league's drug-testing program seriously, and won't, until they ban Toradol. He thinks Japanese players are overrepresented and overpaid. So, too, are Latino players. Black and white Americans don't get enough attention from major-league teams.
B.J. Upton frustrates him: "He has the best tools in the game. I keep telling him, 'You could be great.'" Sheffield says that Upton's the only Ray he thinks about, even though he loves his hometown. Sheffield tried to join the team not so long ago. Other Tampa natives, like Tino Martinez and Fred McGriff, had played their twilight years near home, and Sheffield wanted to do the same. So before the 2010 season he had dinner with manager Joe Maddon, the city's unofficial ambassador (by virtue of his recorded voice playing in the monorail cars that shuttle visitors to and from Tampa International Airport). He never heard back.
His dinner with Maddon was not pleasant. "I was getting disrespected by an organization that had feared me when I stepped up to the plate against their team. They started giving me names of reasons why they couldn't bring me to the team." (Sheffield declined to say which comparison to a veteran Ray angered him, but a peek at Tampa's 2010 roster suggests that it may have been Pat Burrell.) When Sheffield saw that the Rays didn't want him, he retired. But the veterans they brought in after turning him down amused him. "They turned around, right after they told me what they told me, and brought in Manny Ramirez, who quit on two teams, and Johnny Damon -- to DH -- and he doesn't have the power that I have."
Sheffield feels connected to only one team, the Florida Marlins, with whom he won a championship in 1997 and would have spent the rest of his career, if not for a 1998 fire sale. He thinks, when he enters the Hall of Fame -- he’ll be eligible for election in 2015 -- he'll do it as a Marlin.
"Yeah, I think I will make the Hall of Fame,” Sheffield says. “The work I put in justifies that I should make the Hall of Fame. If I don't, there's no true Hall of Fame. I'm talking about someone who dominated for three decades. Numbers don't lie. People do."
Sheffield feels that he shouldn't have any trouble making the Hall, because he has five MVP awards. The baseball record books don't have it this way, but the baseball record books don't really matter to him. "I don't let no person define me, no media,” he says. “In my mind, I know I won five MVPs. I was a better player most times than most of the MVPs were. I was player of the year five times." (The statistical case here isn't great -- he led the league in OPS+ only once, and only twice in his career did he finish in the top 10 in WAR. But he doesn't really care about that.)
* * *
When Sheffield negotiates a new deal for Jason Grilli this offseason, he'll have a chance at a multi-year, multi-million-dollar contract, a rarity for a reliever. But Grilli won't be making anything like the kind of money that Sheffield made. Sheffield says that's a selling point for his agency. "I don't need no player's money,” he says. “I make more money sitting at home than some players make playing, because the Yankees are still paying me and the Tigers are still paying me." Both teams owe him millions in deferred money for the next 10 years. ("Bobby Bonilla, that's where I got the idea from. And they're paying me with interest," he says. "Although I could make that extra percent whether it's in my hands or in theirs.")
When Sheffield negotiates Grilli's contract, he won't aim terribly high. The way he explains it, he'll get his clients what they're worth, not a cent more or a cent less. "If you're not the best player,” he says, “why should you chase the best player's money?" Sheffield says other agents are out there promising players top-dollar and then either falling short, in which case the agent lied to the player, or securing them aspirational, too-big contracts, which will wind up turning the fans against them. "That's how these agents justify that they're good, by making ridiculous demands," he says.
Sheffield says that everyone knows he has a nose for value. "I told the Marlins two years ago, I said Hanley Ramirez should get traded. Where's he at now?"
When Sheffield played for the Dodgers, the front office asked him whether they should pay Shawn Green. Sheffield said yes, and Green came aboard. He lobbied for Kevin Brown, too, although he's not quite as proud of this. (Brown got a bloated seven-year, $105 million contract, the richest in baseball history, in 1999.) "Listen, I fell hard for Kevin Brown," Sheffield says.
But Sheffield always had more luck getting front offices to listen to him about other players than about himself.
When he began his career in Milwaukee, Sheffield says, the entire team turned against him because of minor-league lore. "They tried to pin it on me, that I threw a ball away on purpose in the big leagues. Never happened." Sheffield says something did happen in A-ball, when he was playing for the 1987 Stockton Ports, a Cal League juggernaut that went 94-48. Future major-leaguer Darryl Hamilton threw a ball that short-hopped Sheffield, and Sheffield took the error. He was upset. He yelled at the scorer. This made his manager, Dave Machemer, mad. The next inning, Sheffield threw a ball from short to first as hard as he could, and it sailed into the stands. Machemer walked out onto the field and pulled Sheffield from the game, accusing him of sabotage.
Sheffield says his manager apologized to him in front of the whole team later that night, but the damage had been done. The official scouting report had him as Gary Sheffield, the guy who deliberately threw balls away when he got mad, and that went up to the big club. When he arrived in Milwaukee, none of the veterans, save backup third baseman Ernie Riles, wanted to help him. Sheffield says he'd visit owner Bud Selig's office every day, asking for a trade. Selig wouldn't do anything.
He next went to San Diego, almost won a Triple Crown, and then got traded to Florida. He had problems with the Marlins, too. Jeff Conine, he says, was the corporate face of the team, even though he was the inferior player. The Marlins praised Conine for all his public charity work. But they put a provision in Sheffield's contract -- a six-year, $61 million extension that in 1997 was the richest deal in baseball history, he reminds me -- saying that he had to make charity appearances, otherwise he wouldn't get paid. Sheffield liked the Marlins, though, because they told him that they were building around him, that they'd put a good team together. They did, and they won the 1997 World Series. But then they dismantle the team almost immediately.
Sheffield had a blanket no-trade clause, but Dave Dombrowski and Jim Leyland asked him to accept a trade to the Dodgers. Charles Johnson, the Marlins' catcher, told him that he, Johnson, was in line for a $35 million contract if Sheffield took the trade to L.A. (Scott Boras had told him this). Sheffield didn't want to stand in the way, so he negotiated with the Dodgers for a five-million-dollar cost-of-living raise -- there's no state income tax in Florida, but California taxes are high -- on top of his contract. "They cursed me out. I'd never been cursed out like that," Sheffield says. But they capitulated, and Sheffield, Bonilla, Johnson and some scrubs went west in exchange for Mike Piazza and Todd Zeile.
Everything went wrong there, too. Sheffield says the Dodgers promised him a lifetime contract if he played well. He did: He would eventually hit .312/.424/.573 with 129 homers in three-and-a-half seasons. But the negotiations broke down before his third full Dodgers season, and Sheffield fired his agent. Sheffield hired Boras, who told him he'd get that lifetime deal from the Dodgers if he shut up and hit, and Bob Daly, the Dodgers' chairman, agreed to this premise in a meeting with both of them. So Sheffield shut up and hit. In his final season he had a 1.000 OPS. But the deal still didn't come.
He told Boras to get him traded, and when he couldn't, Sheffield fired him: "I fired Scott Boras because he made a promise to me, and the organization made a promise to me, and they lied,” he says. “If you break a promise, you get fired." Sheffield negotiated his own trade to Atlanta.
As a Brave, Sheffield mashed typically: He hit .319/.412/.562 in two seasons, and finished third in MVP voting in 2003. But he said there was mysteriously little interest in him as a free agent. "I was making 11 million and the Braves offered me four years, 40 million. Every team offered me 10 million or less. If that's not collusion, I don't know what is," he said. "For some reason that year, everybody thought Vladimir Guerrero was a better baseball player than me."
So Sheffield got tired of waiting and called up George Steinbrenner, "my guy who I grew up with in Tampa." Steinbrenner offered him one year and $13 million. "Ain't even close," Sheffield said. "I'm going to come to New York and be the best player on your team." He soon negotiated Steinbrenner upward and signed a three-year deal for $39 million.
Sheffield the Yankee went through a lot. He says he singlehandedly saved Joe Torre's job during a series against the Red Sox at the end of 2005, and that Torre appreciated him for it. (The Yankees wound up clinching the AL East title through a tiebreaker, having a better record in head-to-head games against the Sox. Boston got the wild card. The East’s second-place finisher likely would have missed the playoffs had the Indians not lost six of their last seven.) Afterward, Torre let Sheffield into the meetings of the Yankees braintrust, which had previously been confined to Derek Jeter, Mariano Rivera, Jorge Posada and Bernie Williams. But things fell apart once Sheffield got injured in 2006. Torre told him that there was nothing to the rumors of the Yankees acquiring a new rightfielder, but then they brought in Bobby Abreu. "His power was gone,” Sheffield says of Abreu. “How you gonna pay a guy more than me when he only hits 12 or 15 home runs, not even driving in 100 runs?" And then when Sheffield came back, they sent him to a new position: first base, right after he had broken his wrist on his glove hand.
So Sheffield negotiated his way to Detroit, where his old Florida bosses, Dave Dombrowski and Jim Leyland, were waiting to give him an extension. "I loved those guys," Sheffield says.
* * *
Back at Lit, Sheffield lights up another Rocky Patel -- this one is a Private Cellar -- and he fixates again on a favorite subject, the media members who mistreated him in New York. One was WFAN's Mike Francesa. "Yeah, we used to have that guy on the clubhouse TVs,” he says. “He'd just sit there and talk about Jeter and Bernie Williams, blowing smoke up their asses."
His least favorite media member remains Jon Heyman, then of Newsday and now of CBS Sports. When Sheffield arrived for his first Yankees spring training in 2004, Heyman asked him if he would take a steroid test. Sheffield said yes, and that Heyman could take his blood and urine and save them for 40 years, if he needed to. By Sheffield's account, Heyman chickened out when Sheffield took him up on his offer. He didn't wind up taking the test because Heyman dragged his feet, and the union later instructed Sheffield not to. Heyman's account, which ran in Newsday on Feb. 26, 2004, is typified by this line: "So far he's all talk, and no pee."
Heyman tells me that Sheffield was the only one at fault for the untaken test. “I was all excited, I was thrilled about the story,” he says. “Why would I chicken out?” Still, Sheffield insists that Heyman didn’t give him a fair shake afterward.
He says, "When you try to knock me as a person, I'm gonna get all intelligent on you, then I'm gonna hit you with facts, and then we'll see how far that gets you. I don't always fight, but the ones I fight I win."
Sheffield never went to college, he doesn't have much of a client roster, and he isn't hustling for prospects. But one imagines that he could become a very good agent. He's sharp, tenacious and connected. Former athletes have thrived in the representation business before: Dave Stewart, the former A's pitcher, negotiated Matt Kemp's new deal with the Dodgers, and Sheffield's partner Xavier James used to do legal work for Oscar De La Hoya's very successful promoting company. Even Sheffield's greatest skeptics would have to concede that his plan for the future sounds much better than "Lenny Dykstra, stock-picker." (Sheffield says he would never pursue a business like Dykstra’s. “If you don’t have a degree in finance, you shouldn’t be managing anybody’s money,” he says. “And besides, I don’t care if it’s Lenny Dykstra or it’s Jim Cramer on TV -- the stock market is a gamble. And I don’t gamble.”)
Sheffield also understands, in a way that teams and agents don't, that players are entitled to their own truths off the field. They can do what they want and say what they want, and it won't necessarily interfere with business. Chipper Jones, the loyal soldier, earned $168 million during his career. Gary Sheffield, the itinerant loudmouth malcontent, earned $168 million, too. Jim Thome, Frank Thomas and Ken Griffey, Jr., all colleagues of Sheffield’s in the 500 home run club, colleagues who were routinely tongue-bathed by baseball writers and commentators, earned less.
What Sheffield stands for is a more honest version of baseball, where empowered players don't hide behind spokespeople, and general managers don't manipulate indebted reporters, and agents and owners don't lie. Perhaps his quest will go nowhere. But what if it didn't? Could he actually change the way we experience the game now, where we know players only through their on-field routines, postgame banalities, carefully crafted Twitter accounts and occasional embarrassing drunken escapades?
Sheffield says he can wait. He'll be content with a business that has 30-40 clients, and he'll be content with a business that has zero clients. He's happy to change the game further, but he's happy to depart it, too. "I don't care,” he says. “I'll be off in the corner smoking a cigar."