The biggest obstacle to Jacoby Ellsbury signing an extension that would keep him in Boston long-term might not even be agent Scott Boras’ influence and the likelihood that he’d advise his client to test free agency. Even if Ellsbury and his camp were open to an extension, who exactly would the Red Sox be signing?
The fact is that the 29 year-old Ellsbury is an enigma. He was second in AL MVP voting after a huge season in 2011 (.321 BA, 32 HR, 105 RBI, 119 R, 46 2B, 39 SB). Are they setting a price based on that performance? I’m almost certain that’s what Boras would ask for.
What about Ellsbury's injury-plagued seasons of 2010 and 2012, when he played just 92 games and hit .238 with four homers? The Red Sox don’t want to sign that guy to an extension.
He was a good player in his first two full big league seasons (.729 OPS in 2008, .770 OPS in 2009), but not a superstar-caliber player. Maybe the fair thing would be to pay him as if he’ll be that guy for the next five years.
The point is that it’s hard to see both sides coming to an agreement on how much Ellsbury is worth anytime soon. He’ll likely listen to his agent, play out the season and hope that a bidding war will drive up his price next offseason.
Here are the five teams I think will have the most interest in Ellsbury next offseason.