Red Sox: Past free agency mistakes make Dave Dombrowski cautious

Boras has a history of Jedi mind-tricking teams into overlooking the flaws and overpaying his clients despite the risks. He’s never been afraid to play the waiting game and the deeper we get into winter, the more desperate teams may become.

Dombrowski found this out the hard way. In 2012, when he was the general manager of the Detroit Tigers, Dombrowski signed free agent Prince Fielder to a massive 9-year, $214 million deal.

Fielder was coming off a career year in which he finished third in NL MVP voting but most teams viewed him as a significant long-term risk. While he was only 28 years old at the time and had remained relatively healthy to that point in his career, there were legitimate concerns about how a player with his mammoth body type would hold up over the course of his next contract. Players as large of Fielder rarely have long careers, including his father, Cecil Fielder, who retired at age 34.

The small-market Milwaukee Brewers couldn’t afford to take that risk, not even for a player who developed into a superstar during his seven seasons with the franchise. Once Boras started talking about a $200+ million deal, the Brewers bowed out of the negotiations.

The staggering contract demands scared every team away, yet Boras held firm. When the Tigers lost Victor Martinez to a season-ending knee injury, Dombrowski was sent scrambling for a replacement who could keep Detroit in the mix of World Series contenders. It took until the end of January but Boras was able to dupe a team into giving Fielder the lucrative deal he was seeking.