How Agent Scott Boras Set Up Jacoby Ellsbury's Yankee Deal Eight Years Ago

How Agent Scott Boras Set Up Jacoby Ellsbury's Yankee Deal Eight Years Ago
Agent Scott Boras looks on before a baseball game between the Los Angeles Angels and the Boston Red Sox in Anaheim, California on July 5
Photograph by Jae C. Hong/AP Photo

When news broke last night that Boston Red Sox center fielder Jacoby Ellsbury will sign a 7-year, $153 million contract with the Yankees, many were quick to point out the parallels with Johnny Damon’s departure from Boston eight years ago. Ellsbury, like Damon, had been part of a World Series championship in Boston. Like Damon, he took the highest bid and left for the rival Yankees. Then, as now, the Yankees demonstrated that they are in a league of their own when it comes to cutting checks. And then, as now, Scott Boras was the agent who made it happen.

Damon’s departure stung in New England. He had helped bring an end to 86 years of disappointment for Red Sox fans and had been a central character in the team’s “idiot” identity. Jilted fans from Maine to Rhode Island burned jerseys in their backyards. It’s hard to imagine the reaction will be as fierce this time around. The writing has been on the wall for Ellsbury for months, if not years. Three titles in less than a decade does a lot to relax a fan base. After Damon, everyone is a little wiser, a little less sentimental.

And that is exactly what Boras wanted. In his 2006 book about the Red Sox front office, Feeding the Monster, Seth Mnookin related how Boras bluffed Damon’s way out of town, telling Boston ownership about a 5-year, $65 million offer that probably never existed. The idea was to drive a wedge between Damon and the team and help ease his exit to New York. The maneuver, Mnookin wrote, was not just about getting Damon the biggest payday possible:

“If Boras could orchestrate it so that Johnny Damon, one of the most popular players on one of the most popular Red Sox teams in history, switched sides, what other players might be willing to do so in the future? And how much higher might player salaries go if agents could regularly get the Yankees to bid for Red Sox free agents, and vice versa?”

Now we know.

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