There was never much mystery about what Dustin Pedroia wanted to do. The 2008 MVP did not make a secret of where his priorities stood as he considered whether or not a long-term deal was in his best interests.
At one point, in conversation with team officials, Pedroia contemplated the prospect of crushing a ball, but then watching with dismay as it settled into an outfielder’s glove on the warning track. He imagined feeling a pang of remorse not just about the out, but also at the potential loss of perhaps $50,000 in arbitration or free agency.
The prospect was unsavory. Pedroia did not want to care about the financial implications of his play. He wanted only to care about his team’s performance, and whether he was contributing to wins or losses. The rest, he felt, was immaterial.
“I knew that if I would have gone year-to-year, yes, I probably would have made a lot more money,” said Pedroia. “I understand that. Without a doubt. But I’m here in a place that I love.
“My first thought about the whole thing was that I play for the best team in the major leagues,” he continued. “Who wouldn’t want to play for the Boston Red Sox? We’re going to have an opportunity to win every single year, the fans are the best, this city embraces their team. Why not? It fits.”
Pedroia’s decision was momentous for an organization that, in six years under G.M. Theo Epstein, has worked to become a factory of homegrown talent. The Sox have now demonstrated not only the ability to produce elite players through their farm system, but now to retain them through their prime years as well.
But is the 25-year-old Pedroia the first of many? Will fellow players who made their way from Lowell to Boston, by way of Portland and Pawtucket, soon follow? That is certainly the hope of Epstein.
“I’ll just say that Dustin’s not the only player that we’re talking to this winter,” said Epstein. “It’s significant now that he’s signed, and maybe it will create some momentum…
“Moving forward, (Pedroia) will be one of the leaders of that core of young players that we have. I’d like to think that group’s going to be together for a long time and win some championships for this city.”
Yet for that to happen, some challenges would have to be overcome. As Pedroia has now demonstrated in the form of his six-year, $40.5 million deal, the task is not impossible. All the same, there are factors that make it unclear whether he represents the start of a trend or a lone wolf among the current crop of young Red Sox talent.
RULES OF (MARKET-SIZED) ENGAGEMENT
The deal with Pedroia met a pair of conditions that the Sox require for any long-term deal: the player gave up at least one year of free agency (two, in Pedroia’s case) and was willing to give an option year to the club. (It is worth noting that the option would become void if the Sox trade Pedroia.)
“There’s risk-sharing any time you do a long-term deal,” said Epstein. “We have a club policy for deals of this nature with players in this general service class that we have to get at least one free agent year and we have to get a club option. I think that’s fundamental to making it worthwhile for a club.”
Those conditions may not seem like significant barriers to a contract. The Tampa Bay Rays have five players who have met both of those standards in order to sign long-term deals: third baseman Evan Longoria, outfielder Carl Crawford and pitchers Scott Kazmir, James Shields and Dan Wheeler. Both Longoria and Shields signed their long-term deals before becoming arbitration eligible.
But the atmosphere surrounding extensions for players on smaller-revenue clubs has often been different than what prevails in the sport’s largest markets. The biggest agents, who often encourage their clients to maximize value rather than seek long-term deals, are drawn to young talent in major markets like Yogi Bear to a picnic basket.
One G.M. of a big-market club recalled an instance in which he acquired a minor-league pitcher from a team in the Midwest. Within less than two months, the prospect was represented by Scott Boras.
“If you’re in a smaller market, you can have a sit-down, private discussion about your needs, their needs. It might be easier to find a match,” said the G.M. “(In a bigger market), more people are paying attention. You have the competition of players getting stolen from agents. It’s like everyone has to pay these (big-market) players.”
The big-revenue clubs themselves, meanwhile, can afford to take on more risk and greater cost uncertainty. For Tampa Bay, for instance, the best way that they could afford a player like Shields in 2013 and prevent him from wrecking their payroll through massive arbitration increases was by signing him after a bit more than one full season in the majors.
For teams like the Sox, Yankees, Mets, Angels and Cubs, less of an incentive exists to sign gifted young players to long-term deals. Long-term deals for such teams are a luxury rather than a necessity. The teams in larger markets can afford to pay for performance on a year-to-year basis, even if it means that a player will maximize his potential earnings.
“(Cost) certainty for the sake of certainty has limited value (to the Sox),” Epstein said last month at the G.M. meetings. “We’re lucky with our resources that a little cost uncertainty with some arbitration eligible players doesn’t drastically impact our forecast.”
So, in big markets, two forces often conspire to undermine long-term deals: players are more inclined to seek top dollar, and teams enjoy a sufficient amount of leverage that they will only make deals that represent major savings for players whom they consider excellent bets to perform up to their contracts.
But what does all of that mean for the current core of young Red Sox?
VITALS: 29 years old. 4-plus years of major-league service. Arbitration-eligible for the second time.
ACCOMPLISHMENTS: Finished third in A.L. MVP voting. Led Red Sox in homers (29), RBIs (115) and facial hair (uncountable).
REQUIRED CONTRACT, PER TEAM POLICY: At least three years, with an option.
The ties to Boston are becoming stronger every year for Kevin Youkilis. In addition to being one of the longest-tenured Red Sox, he recently married a Boston-area native. His comfort with this city is apparent, and his desire to stay with the club that drafted him in 2001 is genuine.
“I think there’s nothing that Kevin would like more than to be a guy who plays his entire career in Boston,” Joe Bick, Youkilis’ agent, said last month. “He loves it there, the people there have been wonderful to him. It’s a tremendous atmosphere for him.”
All the same, Youkilis understands clearly the nature of the business. He is the players’ union representative for the Sox, and believes in the value of embracing—rather than bucking—fair-market value.
The 29-year-old, who finished third in A.L. MVP voting, is well aware that he can maximize his earnings through a series of one-year contracts leading up to free agency. Whether he would take a deal of at least three years plus a team option remains to be seen.
According to one baseball official, the arbitration-eligible Youkilis is likely in line to bump his salary from $3 million in 2008 to the $5.5-6.5 million range in 2009. He now has more than four years of major-league service time, and is two seasons from the chance to cash in on a free-agent payday.
There is openness to the idea of a long-term deal with the Sox, but no urgency. Last year, Youkilis and the Sox briefly discussed the possibility of a multi-year deal before almost immediately realizing that a fit wasn’t there.
That was before Youkilis had an exceptional 2008 season, one in which he was the Red Sox’ foremost power threat (29 homers) and run producer (115 RBIs) while ranking among A.L. leaders with a .312 average (6th), .390 OBP (6th), .569 slugging (3rd) and .958 OPS (4th).
With those numbers, the class to which Youkilis would compare himself in a long-term deal has changed. A long-term deal this offseason will be even more expensive than it was a year ago. While Youkilis would like to see a deal get struck, he is hedging his bets about whether it might happen.
“As long as I can keep playing in the major leagues, playing for the Boston Red Sox, that’s a great thing. Hopefully I’ll be here for a long time,” Youkilis said on the day that MVP voting was announced. “I’ve got two more years (of contractual control by the Red Sox). We’ll see. We’ll see what happens.”
VITALS: 28 years old. 3-plus years of major-league service. Arbitration-eligible for the first time.
ACCOMPLISHMENTS: Holds record for most postseason scoreless innings (25) to start a career. Second-lowest ERA (1.84) of any pitcher in baseball history (min. 200 innings). Accomplished dancer.
REQUIRED CONTRACT, PER TEAM POLICY: At least four years, with an option.
Jonathan Papelbon, like Pedroia, is represented by agents Seth and Sam Levinson. Yet it would be misguided to suggest that common agents will lead to a common set of negotiating preferences.
Last spring, Papelbon very publicly talked about his desire to set the bar for closers. He pronounced great enthusiasm with the idea of going year-to-year in contract discussions, feeling that the shoulder program that he has followed since a season-ending shoulder injury in 2006 will all but guarantee his health for the long haul.
Papelbon openly relished the notion that, starting this offseason, negotiating leverage would begin shifting from club to player as he became arbitration eligible. The baseline for Papelbon’s 2009 salary will likely be the $5 million former Dodgers closer Eric Gagne received after three big-league seasons in 2004.
A little more than three years into his major-league career, Papelbon already is in an historic class of relievers. He expects to be paid as such—something that is entirely within his rights.
But Sox officials have noted on many occasions that the performance of relievers is extremely volatile on a year-to-year basis. That uncertainty is reduced somewhat for closers, whose usage can be regulated more carefully than other bullpen members, but it’s still a puzzle to maintain the health and performance of closers over the long haul.
That being the case, it seems unlikely that he will not consummate a long-term deal with the Sox. Indeed, it would not be a shock if he became the first Red Sox player during Epstein’s tenure to see the arbitration process to its conclusion.
VITALS: 24 years old. 2+ years of major-league service. Not arbitration eligible.
ACCOMPLISHMENTS: Led Sox with 3.21 ERA, 210.1 regular-season innings. Career 2.25 postseason ERA. Capable of ripping a hand off a forearm with vise-like handshake.
REQUIRED CONTRACT, PER TEAM POLICY: At least five years, with an option.
Jon Lester emerged this year as one of the elite pitchers in the American League. Yet even with his dominance, the Sox might have reason to wait for at least another year before offering him a long-term deal.
Foremost, given the massive bump in innings that Lester had in 2008, the Sox will likely want to see whether the left-hander will remain healthy following a 237-inning workload. That would be in keeping with the general approach of the club to the idea of extensions.
Teams like the Rays are willing to accept greater risk of performance declines in order to sign players at severely discounted rates early in their careers. But for the Sox, because they can afford the pay-for-performance model, there is little reason to bet tens of millions on players who have yet to prove that they can not only achieve but sustain great success.
Pedroia has already done so, as demonstrated by the neighboring Rookie of the Year and MVP hardware in his house. Lester may well be growing into a perennial Cy Young contender, but there are not yet two data points to demonstrate such a trend.
Unless Lester is willing to accept a deal that could diminish significantly his earnings over the next five to six years, the team seems Sox have good reason to wait until after the 2009 season to figure out if it can find common ground, especially since the Sox have signed just one pitcher (Daisuke Matsuzaka) to a deal or five or more years.
VITALS: 25 years old. 1+ years of major-league service. Not arbitration eligible
ACCOMPLISHMENTS: Finished third in Rookie of the Year balloting and led American League in steals. Above-average centerfield defense. Never dropped the chalupa.
REQUIRED CONTRACT, PER TEAM POLICY: At least six years, with an option.
Jacoby Ellsbury is also a Scott Boras client, and the agent is known for trying to steer his players to free agency as quickly as possible. That said, Boras clients have been known to give up both free-agent years (Jason Varitek, for instance, did so with a four-year deal with the Sox from 2001-04) and to have team options written into contracts (Derek Lowe’s first free-agent year was delayed by a Sox team option in ’04).
Based on the model of performance certainty, the Sox might want to see the kind of progress Ellsbury makes between his first and second full seasons before offering a deal. All the same, if the team wants to capitalize on a potential buy-low moment in his career, then it would be rather interesting to see whether Ellsbury would be receptive to talks of an extension.
Alex Speier is a senior writer for WEEI.com.