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Jon Lester free agency preview

Steven Bisig-USA TODAY Sports

If the Red Sox play their cards right, the deal that brought over outfielder Yoenis Cespedes at the non-waiver deadline might become the biggest steal of the year.

In the trade, the Sox sent left-hander Jon Lester and outfielder Jonny Gomes to the A's in exchange for Cespedes and a 2015 competitive balance Round B pick. But if Lester re-signs with Boston this winter, the team will have essentially traded Cespedes and that pick for Gomes (who has a .664 OPS this season), minus half a season of Lester on the Sox' last-place squad.

But will Lester really return to Boston? Is he worth the risk of a huge long-term contract that will take him into his late-30s? Do the Red Sox have other options? Probably, maybe and yes. Here, we'll take a closer look at the (longer) answers to those questions, and more.

Where he's been

Lester is nearing the end of his ninth year (seventh full) in the majors, and his career numbers show that he's consistent, durable and experienced in the postseason—with plenty of success there.

The Red Sox drafted Lester in 2002, and it took him awhile to make it out of the minors. He spent three full seasons there, moved to the majors for part of 2006, then found himself back in the minors at the start of 2007 before finally hitting the big leagues for good in 2008.

Since that permanent promotion, Lester hasn't looked back. His most recent start made 2014 his seventh straight season with 30 or more starts, and he's eclipsed 200 innings in all but one of those years. That durability adds a considerable amount of value, especially in an age in which lengthy contracts to pitchers are being viewed as more and more risky.

In fact, Lester just might be the safest investment of the three big-name pitchers (Max Scherzer and James Shields being the other two) who will become free agents this offseason. Part of that stems from Lester's consistency; his ERA and FIP have remained well under four in all but one of his seven full seasons.

The flip side of that, however, is that Lester's 157 ERA+ this season is uncharacteristic, to say the least. It's a 47-point increase from last season and nearly twice his 87 ERA+ from 2012, though that latter total is quite a deviation from the other ones Lester has posted throughout his career.

Even so, during the three seasons following Lester's fourth-place finish on the 2010 Cy Young award ballot, he posted a combined ERA of 4.03. His performance this season has pretty much squashed any concerns, but it's worth noting that Lester hasn't been quite this good during the few seasons leading up to 2014.

But Lester has also spent his entire career in Boston (outside of nine starts with the A's), perhaps the toughest pitching environment in baseball over the last several years outside of New York and Colorado. One could argue, combining park factors and strength of opposition, that the Red Sox are the most difficult team to pitch for in the majors, and that's an important point that National League teams would do well to consider.

Where he is now

Lester is having the best season of his career, and he picked the right time to do it. He never had an ERA below 3.21 before his 2.45 total this season, and he's striking out a batter per inning—his best rate since he led the league with a 9.7 K/9 total in 2010. On top of that, Lester is also allowing homers at his lowest rate since 2010, and his 2.0 BB/9 is a career best.

Not only is Lester having his best season at a good time, he's also having the best stretch of his best season at the best time. He has a 1.91 ERA dating back to August 23, a five-start span, and all of his nine starts with the A's have been "quality starts." In fact, his last non-quality start came on June 7. He's made 17 starts since then.

Somewhat paradoxically, Lester has been at his very best for an A's squad that started to free fall once he came over at the trade deadline. He earned Player of the Week honors last week, and his 2.30 ERA in 62.2 innings with Oakland, despite a 3.27 FIP, has Lester set up for a big paycheck this offseason.

Where he's going

It seemed preordained at one point that Lester would return to the Red Sox this offseason, and in many ways, that's still a likely scenario.

But reports also indicate the Cubs' interest, and President Theo Epstein has noted that his team will have money to spend this winter.

"Because we have so many young players who are going to be cost-controlled over the next several seasons, we have tremendous flexibility built into our roster as it is," Epstein said via CSN Chicago's Patrick Mooney. "We’re going to field a pretty good nucleus with a very low payroll associated with that."

Epstein went on to note that the payroll freedom will allow the Cubs to be "very aggressive should the right player or players present themselves."

Lester just might be the "right player."

Of course, the left-hander spent several seasons in Boston with Epstein, and that familiarity could prompt the Cubs to pursue Lester. The team also needs to find a starter to build its rotation around, and there's no tellling if the top starters with expiring contracts next offseason (David Price, Johnny Cueto, Jeff Samardzija, etc.) will re-sign with their current clubs. For a team that projects to contend in a year or two, now might be the time to act.

The Red Sox might feel the same way, given the pressure stemming from (most likely) finishing in last place in the AL East for the second time in three seasons. As noted in Max Scherzer's free agency preview, Sox chairman Tom Werner said the team has "a lot of money to spend," and with the rotation loosely resembling that of a Triple-A squad, it would be an understatement to say pitching is at the top of the Sox' wish list.

The Yankees might also take a look at Lester this offseason, with a rotation that's far from a sure thing. As we learned this season, the Yanks don't have a backup plan for when Masahiro Tanaka and CC Sabathia go down. Lester would give the rotation some stability, and his track record means the Yankees wouldn't have to worry about his health—unlike their other top starters.

The limiting factor, of course, is the Yankees' budget, and they'll likely be approaching a $200 million payroll by the time Lester hits the market, with all their potential re-signings and whatnot. But if the Yankees are willing to shell out some additional cash, Lester might be looking at a huge offer from a team that's no stranger to, well, huge offers.

Plus, the Yankees mean business when it comes to the playoffs, and Lester's 2.11 ERA in 11 postseason starts (13 total appearances) gives him a sizeable advantage over fellow free agents Scherzer and Shields.

Other big-spending teams will likely enter the conversation, but for now, the Red Sox, Yankees and Cubs all seem like the most likely destinations for Lester, and it's not really close. At the end of the day, it's where Lester and his family want to go, and with a great baseball city, a foundation for future success and a management team that Lester respects, Chicago appears to be a mighty appealing destination.