Free agent roundtable: Will Jacoby Ellsbury reunite with Theo Epstein?

Jacoby Ellsbury is likely set to sign a huge deal in free agency.
Jacoby Ellsbury is likely set to sign a huge deal in free agency. (USATSI)

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After winning his second World Series ring as a member of the Boston Red Sox, center fielder Jacoby Ellsbury is set for free agency and could land the biggest deal this side of Robinson Cano this winter. Where are his possible landing spots? Well, the most dramatic would probably be a reunion with former Red Sox general manager and current Cubs president Theo Epstein.

Let us discuss.

Matt Snyder: Will he leave Boston? If he does, what about a reunion with Theo Epstein? It was under the Epstein regime in Boston that he was drafted (1st round, 2005) and developed.

The Cubs also make sense for a number of reasons.

1. They don't have a current surefire center fielder or leadoff man. Ellsbury is one of the best in both of those spots right now in the majors.

2. Highly-touted center field prospect Albert Almora is only 19 and played only 61 games in Class A this past season. So he's several years away. In fact, by the time he's ready to join the big-league Cubs -- if he doesn't flame out, which is always a distinct possibility with prospects -- it would also be about the time Ellsbury is to the point in his career that he needs to transition to a corner outfield spot. Keep in mind, he's 30 and will likely command a deal of at least four years, probably longer. Shane Victorino, for example, was 32 this season and transitioned beautifully to right field. Perhaps Ellsbury needs to do so at age 33 and that's when Almora is ready to take over in center? It could fit quite well.

3. The Cubs keep saying they aren't going to spend much money and maybe they won't. But they went four years and $56 million for a mediocre Edwin Jackson last season and the number of dollars they have committed per season moving forward -- compared to what they could spend -- is real low. They have money.

4. It definitely won't hurt to have a two-time World Series champion joining the locker room with the likes of youngsters Anthony Rizzo and Starlin Castro who haven't been part of a winner. Ellsbury could go from being a follower to a leader. He's learned from excellent leaders like David Ortiz and Dustin Pedroia, so he'll be ready.

Obviously it might be a tough sell for Epstein to convince Ellsbury to leave a winning situation for a rebuild, but dollars generally solve the problem. Plus, Ellsbury already has two rings and what about convincing him that his third will be the drought-ender in Wrigley Field? Being part of something like that has to be enticing. So the sell job is convincing Ellsbury that it can be done.

Mike Axisa: I've seen speculation that now that Ellsbury has won his two rings, he might go for the pure money grab in free agency and take every last cent. I'm not sure if I buy that, but obviously money will be a huge factor either way.

The Cubs make sense and I think they're closer to contention than a lot of people realize, but I wonder if Epstein & Co. are willing to commit that long to a player at this point. Ellsbury is great but he's not all that different from Michael Bourn -- once his legs start to go and his stolen base totals come down and defense starts slip, it'll go south in a hurry. He can't help you many other ways.

The Rangers have reportedly coveted Ellsbury for a long time and he makes a lot of sense for them. If they sign him, they could then turn around and use Leonys Martin in a trade to shore up another hole. The Mariners could be a fit since Ellsbury is from Oregon, but the hometown stuff is almost always overplayed in free agency. If the Reds don't think Billy Hamilton is ready, Ellsbury would look marvelous atop their lineup and in center field. He won't have Shin-Soo Choo's gaudy on-base percentage but he's a better all-around player. Simply put, a player of Ellsbury's caliber would help many teams.

Dayn Perry: I'm a bit of an Ellsbury "agnostic." Don't get me wrong, he's a good player -- plus defense at an up-the-middle position and the best base-stealer in the game today. However, I also see a guy who's posted a better-than-league-average OPS+ just twice in his career (counting qualifying seasons only), and I also see a guy who's lost more than 250 games to injury in his career. Sure, a number of those have been "impact" injuries of some kind, but eventually you begin to suspect that his style of play makes him susceptible to that kind of thing. I also see a lot of year-to-year volatility at the plate. And speaking of hitting, I also see career numbers that are being lifted up by an outlier 2011 season that, frankly speaking, will never happen again. I like Ellsbury as a player, but he's not a guy I'd be willing to pay market rates for, assuming the rates are what I think they'll be. That's especially the case now that he's moving beyond prime-performance age range.

Snyder: I think it's reasonable to believe in the next five years that Ellsbury will perform as he did in 2013 (.298/.355/.426, 114 OPS+, 5.8 bWAR along with 20-plus games lost to injury) three or four times. If that's the case, he's well worth an eight-figure-per-year salary but not $20 million a year. If he's going to get something like five years and $100 million, I think that's an overreach. If he gets a deal similar to Bourn (four years, $48 million), I'd call it a huge bargain -- especially if it's a team like the Cubs or Mariners looking to make a splash. The best guess is he ends up getting something in between (5-$75M?).

CBS Sports Writer

Matt Snyder has been a baseball writer with CBS Sports since 2011. A member of the BBWAA, he's now covered the last six World Series beginning with the epic 2011 Fall Classic. The former Indiana University... Full Bio

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