The Craftiest Man on the Diamond

November 16, 2009 - 8:02 pm

He is the one baseball fans love to hate. He is the Grinch that stole the offseason. He is the Ebenezer Scrooge who says "Humbug!" to hometown discounts, harmonizing negotiations and a love for the game over a love for money. He has every trick up his sleeve and a knack for getting every little bit that he wants. He is none other than the notorious agent himself: Scott Boras. Sure, maybe Boras, as Curt Schilling says, "has no shame." He certainly has no problems hyping players beyond their value, constantly painting them as a grand prize to be won and a gift to be blessed with. If Boras had his way, tapping into Johnny Damon's stem cells would come close to discovering the fountain of youth and Matt Holliday -- a potential target of the Red Sox -- would serve as the poster-boy for the definition of a complete player. Still, despite his crafty and cunning reputation, his sly fox persona, and his devious business tactics, Boras is still the leading agent in the world of negotiations. He attracts love from the players who are all about the Benjamins and draws anger from the general managers who are all about the luxury tax. When it comes to the Red Sox, Boras has had quite a topsy-turvy history with the Fenway front office. From allowing Boston icons to become modern-day Benedict Arnolds to allegedly failing to advise his client he could make more money by accepting arbitration, Boras had made it clear that any deal that involves exchanging numbers with him is sure to spark some level of controversy. Here's a look at recent events in the past few years between the customers of Boras and the Red Sox executive staff. Johnny Damon The Caveman himself vowed to never play for the Yankees. Yet when New York offered Damon a couple of million a year more than the Red Sox, Damon listened to his agent's advice and took the money and ran. (With all that hair, a trip to the barbershop is worth more than a pretty penny.) After the 2005 season, Boras proposed his client with a weak throwing arm was set to receive a six-year, $72 million contract or  seven years at $84 million. Stunned by the ludicrous request, the Sox instead, offered Damon a four-year, $40 million deal with the possibility of raising the salary to the $44 million range. To the shock of Red Sox fans around the country, Damon let the money talk when he signed with the rival Yankees for four years and $52 million, prompting an unprecedented press conference by the then-Theo-less Red Sox to discuss the departure of a free agent in a deal that had not yet been announced by the team that signed the player. Daisuke Matsuzaka After missing the postseason in 2006, the Sox knew they needed a bold offseason. When Japanese right-hander Daisuke Matsuzaka declared he wanted to pitch in America, the Sox brass won a $51.1 million posting bid just to open up talks with the former Seibu Lions ace. The Sox were given a 30-day deadline to strike a deal. If a contract was not in place by then, the Sox would forfeit their rights and Matsuzaka would have to return to Japan for the season. Of course, Boras had no intention of taking the easy route to grant his client his dream to pitch in the United States. When talks stalled just days before the deadline, many speculated that Boras and the Red Sox would fail to settle on a deal since Boston figured the posting fee would play into the contract. Finally, the Sox brass flew across the country to Boras' office in Southern California, where they reached an agreement at last on a six-year, $52 million deal along with plenty of extras and bonuses included in the package. J.D. Drew When J.D. Drew opted not to sign with Philadelphia after the Phillies selected him as the second overall pick in the 1997 draft, Drew instantly became a target for jeers and sneers in the City of Brotherly Love. After spending a few season in the St. Louis Cardinals outfield, Drew played one season for the Atlanta Braves before signing a five-year, $55 million pact with the Dodgers. Two seasons later, Drew decided to exercise his opt-out option in November 2006, becoming a free agent. With the Sox in need of an outfielder, Drew seemed like a natural fit to replace some of the power that was lacking in the lineup. Though both parties reached an agreement early, it took 52 days for the five-year, $70 million deal to be finalized in January 2007. Concerned about his health, the Sox were adamant about constructing an insurance clause in case Drew' right shoulder prevented him from playing a certain number of games. Boras obviously thought the right fielder was worth a tick over $14 million. Mark Teixeira Teixeira's gold glove and World Series ring could have been engraved with a Red Sox 'B' instead of a Yankees 'NY.' When the Red Sox announced they were prepared to offer Teixeira a deal that would be the longest and the richest in the seven-year history of the John Henry ownership group, many thought Boston would be the landing spot for the marquee free agent. Yet, as was the case with Damon, the Yankees lured Teixeira away, inking him to an eight-year, $180 million deal. Boras spoiled Christmas for the Sox once again. Jason Varitek Boston fans were thrilled when Varitek made a rare move by remaining with the Red Sox at a lower price at four years for $40 million after winning the 2004 World Series. But in the last offseason, Boras convinced Varitek that despite his declining numbers, he deserved more than the Red Sox were willing to give. When the Red Sox offered their captain arbitration, Boras advised his client to turn down the acceptance. Unaware (according to a report a year ago) that if he had accepted arbitration he would be guaranteed a raise, Varitek ended up saving the Sox a couple of million after agreeing with Boston on a one-year, $5 million deal with an option for 2010 that Boston could pick up for $5 million or Varitek could pick up at $3 million. Varitek chose to exercise his player option last week, yet the $8 million he'll earn over his two years in Boston is less than he would have received in 2009 alone had he accepted arbitration.