The Dual-Edged Sword of Hiring Gary Sheffield as an Agent

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A player agent with experience might’ve had it in mind that there was the possibility—injury or trade—that his client’s new contract might require a few “if-then” incentive clauses. That doesn’t appear to have been the case with Jason Grilli whose agent, Gary Sheffield, didn’t get such clauses inserted into the contract Grilli signed to return to the Pirates. Because of that, as Grilli is set to take over as the Pirates’ new closer once the Joel Hanrahan to the Red Sox trade is finalized, he will collect his salary for 2013-2014 (2-years, $6.75 million), and not get one penny more whether he saves 40 games or 0.

Was Sheffield required to do more and what’s the trade-off when Grilli shuns an established agent who might see Grilli as a low priority and opts for Sheffield, who doesn’t have a long list of clients?

In the past, agents like Scott Boras have treated their lower-tier clients as moderate inconveniences, expecting them to be happy to take a back seat to the big names and wait their turn. Felipe Lopez was such a player who pushed back in February of 2010 when he fired Boras. Lopez wasn’t in Grilli’s situation when Grilli hired Sheffield in 2010. Grilli was out of baseball and looking for work; Lopez, in 2009, had had one of the best seasons of his career with a .310/.383/.427 split and 9 homers for the Diamondbacks and Brewers. Lopez was a flawed player, but should’ve gotten a suitable job offer before February considering his bat, pop and that he was defensively versatile playing a passable second and third base.

Boras’s reaction wasn’t an apology to his client or an explanation. Instead, he announced that he was going to “confront the player,” and made cryptic references of “reasons” why Lopez wasn’t offered a job that he declined to disclose. It’s as if he—the employee—was in charge and was exacting revenge for being fired. Boras is powerful and Lopez had little leverage, but in the end, Boras worked for Lopez, not the other way around.

While Sheffield might not have the most sparkly reputation around the executives and teams that he angered throughout his career and that is definitely going to hurt the players he represents because they simply will not want to deal with Sheffield, he’s going to speak up and fight for the people on his side. His clients—Grilli and Josh Banks—weren’t in a great position to bargain. They were looking for work. Would someone have signed Grilli and Banks without Sheffield? Probably. But what’s the difference? Maybe players like these need someone like Sheffield who has nothing to gain by representing them instead of Boras who probably has lower level associates handling the Lopezes of the world on a daily basis and forgets about them completely until they do what Lopez did and publicly fires him, embarrassing him. Boras certainly couldn’t let that go by without face-saving response.

Grilli’s main obstacle as a closer is handling it mentally. The Pirates have a shot at a playoff spot in 2013, so his closing opportunities will be important. Pitchers in the past that have proven themselves as set-up men and couldn’t close have been legion—one in particular last season was David Robertson of the Yankees, who looked as if he was about to hyperventilate on the mound when he took over for Mariano Rivera, then got hurt. It opened the door for the more proven Rafael Soriano and Robertson went back to being a set-up man. It’s not that Soriano’s stuff is better than Robertson’s—it’s not—but Soriano can close. Whether Robertson can or not remains to be seen. The first impression wasn’t good.

That mentality, more than stuff, is the key to closing. Grilli’s strikeout numbers have spiked and he’s found a velocity in the mid-90s that he didn’t have earlier in his career. He has a chance to be good at the job that Sheffield the agent clearly didn’t expect his client to have. Should Sheffield and his partner, lawyer Xavier James, have realized that there was a chance that Grilli could accumulate a few saves and prove himself as a closer, possibly putting himself in line to make a lot more money? Yes. But Grilli is also 36 and his annual salary for a 15 year professional career surpassed $1 million for the first time in 2012. Taking the guaranteed cash was the smart move. Another agent would’ve insisted on the clause and that might’ve wound up costing Grilli the opportunity and left him sitting out and waiting as Lopez was.

It’s a dual-edged sword. Sheffield, perhaps unwittingly, served his client and got him a guaranteed two year contract in the now. That’s not a bad thing.

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Hurdle’s Law vs Murphy’s Law—Fighting for the Future of the Pirates

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Pending a physical, the Pirates have agreed to a 2-year, $14 million contract with free agent lefty Francisco Liriano. This winter, in addition to Liriano, the Pirates have added catcher Russell Martin (2-years, $17 million) and retained pitcher Jason Grilli (2-years, $6.75 million negotiated with Grilli’s agent Gary Sheffield. Yes. That Gary Sheffield.) These moves follow last spring’s acquisition of A.J. Burnett from the Yankees and the summer trade for Wandy Rodriguez from the Astros. During the 2012 season, they also received cheap and talented youngsters Travis Snider from the Blue Jays and Gaby Sanchez from the Marlins.

Liriano’s acquisition mirrors the Pirates’ trade for Burnett. Liriano is a superiorly talented underachiever whose results will benefit from the National League and the big Pirates’ park. Looking at the club on the whole, the Pirates have a batch of young players that they’re in the process of surrounding with veterans who have playoff experience and have played for well-run, winning organizations.

The Pirates collapsed in the second halves of both 2011 and 2012; endured rightful public indignation at their assistant GM Kyle Stark implementing ridiculous physical and mental training techniques for their minor leaguers; and struggled to shake the hapless image that has been their albatross for two decades. The entire front office from team president Frank Coonelly to GM Neal Huntington to Stark were said to be in jeopardy of losing their jobs at the conclusion of 2012 and still aren’t completely secure, but owner Bob Nutting retained all three, staying the course along with manager Clint Hurdle and trying—not putting forth the pretense of trying, but actually trying—to win by spending some money.

They haven’t simply taken on onerous contracts of other clubs either, nor have they drastically overpaid in terms of years/dollars to get veteran help. The Pirates got Burnett from the Yankees for low level non-prospects while paying a third of Burnett’s $16.5 million salary in 2012 and will pay half in 2013. They got Rodriguez from the Astros for three nondescript minor leaguers and are paying $8.5 million of his $13 million salary. Now with Liriano, the rotation of Burnett, Rodriguez, Liriano, James McDonald and as early as 2013, Gerrit Cole, the Pirates can compete. Andrew McCutchen is a true all-around star and MVP candidate; Pedro Alvarez has tremendous power; and with Sanchez, Martin, Neil Walker and Garrett Jones, they’ll score enough to support that starting rotation. In the weakened National League Central—with only the Reds substantially better on paper—and the extra Wild Card, there’s an opening for the Pirates.

The front office is constantly on the precipice of doing something stupid and are discussing trading closer Joel Hanrahan. What they get for him and whom they use to replace him should be planned before pulling any trigger and I wonder whether Hanrahan’s pending free agency after 2013 is more of a catalyst to this talk than any potential return or concerns about the righty’s effectiveness. I would not trade Hanrahan unless there are extenuating circumstances or the offer is too lucrative to turn down. They’re going to need him.

As always, there’s a dubious nature surrounding the Pirates’ plans and intentions and much of their rise has been due to a vast number of high draft picks and not overwhelming wisdom from the front office. But in spite of the collateral stories and questioning glances, there’s much to be enthusiastic about in Pittsburgh and it’s not Sidney Crosby (if the NHL ever plays again) or Ben Roethlisberger. It’s McCutchen, Cole and the other youngsters the Pirates have developed along with their shiny new veterans. Players are no longer shunning the Pirates or going to Pittsburgh because they have nowhere else to go. Given the team’s reputation around baseball as a wasteland where young players run out the clock to free agency and veterans go for a final job, that new perception is not a small thing.

There’s still that hovering feeling of Murphy’s Law that everything that can go wrong will go wrong, particularly because of the still shaky status of the front office and the owner’s blindness to the harsh and exhausting realities of being a baseball player. It’s highly possible that Nutting’s expectations will outweigh what the team can accomplish and he’ll let his displeasure be known early if the team isn’t markedly better immediately. At that point, changes might be made in the front office.

Even with the looming dysfunction, they have enough talent to rise from the ashes of their 2011-2012 stumbles, use them as learning experiences, and contend for seven months rather than four. Murphy’s Law says that the Pirates will remain the Pirates, but that’s being counteracted by Hurdle’s Law—the law that dictates not taking crap and not making excuses.

They have the talent to win. And they just might.

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