It's not that Ellsbury isn't a very good player, he is. But, he and his agent are going to expect Ellsbury to be paid like he is a great player, which Ellsbury has only resembled once in his career, during the 2011 season.
The 30-year-old Ellsbury will be going into the prime of his career, but he has struggled with durability, something that should give the Red Sox pause about re-signing him to a $100 million-plus deal. Given the lack of offense around baseball and Ellsbury's unique skill set, his market might surge far above the $150 million range.
This year's surprising World Series victory allows Red Sox general manager Ben Cherington to be a very discerning shopper this winter. Paying for future performance is the only way to go. Paying elite money to good players is the easiest way for the Red Sox to lose their way again on and off the field.
The time is perfect for Ellsbury to leave and see what the MLB market has to offer. He will have the unique ability to say that his first and last seasons in Boston resulted in the Red Sox winning a World Series. Ellsbury burst onto the scene in 2007 during the playoffs and World Series, giving the Red Sox a taste of what was to come. No one will begrudge him the opportunity to leave and seek a bigger contract or play closer to home.
Boston's management will be concerned with replacing a player who hit nine home runs, stole 52 bases and produced a .355 OBP, hardly numbers that jump off of the page. This isn't to downplay or diminish Ellsbury's performance last season, it is to simply state that the Red Sox should be able to find a comparable player at a much cheaper cost.
The Red Sox might be much better served to give top prospect Jackie Bradley Jr. an opportunity next season while finding another player to split some time between center and right field as protection.
One player who might fit the bill for the Red Sox is Norichika Aoki of the Milwaukee Brewers. Aoki would produce somewhat comparable numbers to Ellsbury's at a fraction of the cost. Aoki is scheduled to make only $1.95 million next season, and he won't be eligible for free agency until the 2018 season. The 31-year-old Aoki would pair nicely with Bradley Jr. and Shane Victorino to rotate between center and right.
The other interesting aspect to letting Ellsbury go is the potential for the Red Sox to get an additional top pick in the 2014 MLB draft. The Boston farm system continues to develop exciting players who can support the major league roster each year. Giving the Red Sox two of the top picks next summer only strengthens the organization long-term.
If there is a chance to keep Ellsbury at a reasonable cost this winter, then it is something that needs to be explored by the Red Sox. Ellsbury has shown he can thrive in Boston and the demanding AL East. But, if Ellsbury leaves, it is with the understanding that he gave the Red Sox seven very good seasons and two World Series titles and it was simply time to move on both sides.
Is Ellsbury worth $20 million a year? If the answer is no, then it's time for the Red Sox to move on. Sometimes it can be that easy.