Chances of Boston Red Sox Landing Each of Their Expected Offseason Targets

If the Boston Red Sox are going to compete once more in 2015, they'll need to do some serious work when it comes to overhauling parts of their roster.

The Red Sox need more starting pitching. They need bullpen help. They may need a backup catcher, and they'll probably look into acquiring a starting third baseman, too.

This wide scope of needs has led to plenty of speculation as to who the Red Sox will target in the coming months, even as the World Series has yet to come to its conclusion. And you can expect the rumors to increase in intensity as the hot stove heats up.

While it's a bit early to handicap which players the Red Sox actually have a chance at acquiring, it's still a fun exercise, and it can also be instructive in that it will allow us to watch how our notions of who Boston will sign can change and develop over the length of an offseason.

With that in mind, let's take a look at the five free-agent targets the Red Sox are most frequently linked to and their respective chances of signing with the Sox before the 2015 season begins.

Jon Lester, LHP

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Will the Red Sox earnestly attempt to bring back Lester this offseason, or will they merely enter negotiations with their former ace to save face?

It's a tough question to answer, and while the Sox will offer up every platitude about wanting to bring Lester back to Boston, there's probably some genuine interest, too.

The Red Sox's rotation was absolutely atrocious following the jettisoning of Lester, John Lackey and Jake Peavy, and none of Boston's bevy of young starters truly stepped up and claimed a spot in the rotation for himself. The Red Sox need to acquire at least two starting pitchers this offseason, and you can make the argument that they should acquire three or four.

Lester is either the best or second-best arm available on the free-agent market, depending on how you feel about Max Scherzer, and obviously makes a ton of sense for Boston. He projects out as a dominant force for the next several years, as Baseball Prospectus' Jeff Moore wrote on Tuesday, he's proven his ability to thrive in Boston and he's a New England fan favorite, to boot.

The problem, of course, is that Lester is going to require an enormous financial investment. CBSSports.com's Jon Heyman reported that Lester could get as much as $189 million over seven years, with other more "conservative" estimates coming in at around $175 million. Given the history of long-term pitching contracts, that's a scary proposition.

Still, competition for Lester figures to be fierce. The Chicago Cubs, per ESPNChicago.com's Jesse Rogers and many other sources, have been frequently cited as interested parties in the Lester sweepstakes. And Lester would make sense for other teams with cash like the New York Yankees and Los Angeles Dodgers.

In the end, there's just been too much that's transpired between Lester and the Red Sox, and there figures to be too much competition this offseason. There's a chance he re-signs with Boston, but fans shouldn't hold their collective breath.

Odds of Signing with Red Sox: 25 Percent

Justin Masterson, RHP

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Mentioned by The Boston Globe's Nick Cafardo as a potential fit for the Red Sox, Masterson makes a lot of sense for a team that needs to add both top-of-the-line and mid-rotation pitching.

Masterson suffered through an abysmal 2014 season, posting a 5.88 ERA in 128.2 innings with the Cleveland Indians and St. Louis Cardinals. But he battled a knee injury for much of the season and was coming off a several-year run of success as a solid No. 2/3 starter in the AL.

It's tough to predict what type of deal Masterson is going to get as a free agent. He may want a one-year deal to try and re-establish his value for a big payday in 2016, or he may bank on his track record outweighing his recent struggles and shoot for a two- or three-year pact.

If Masterson opts for the former, don't expect the Red Sox to win out; Fenway Park isn't a great place for a pitcher to rebuild his value. If Masterson wants stability, though, it would make some sense for him to look to a return to Boston.

You can expect at least half the teams in baseball to show some interest in Masterson this offseason, so it's tough to put odds on the right-hander landing in Boston. But they'd certainly appear to be among his five or six most likely and qualified suitors.

Odds of Signing with Red Sox: 15 Percent

Pablo Sandoval, 3B

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The title for "most Red Sox-related rumors" still belongs to James Shields for now, but Sandoval is quickly gaining steam in what figures to be a close race all offseason.

Even as the affable third baseman is fighting for his third World Series ring, rumors abound that the Red Sox will make a significant play for his services. CBSSports.com's Jon Heyman was one of the latest to report that Boston is interested in Sandoval, who he says is seeking a deal in excess of $100 million.

It's not difficult to comprehend why the Red Sox would have interest in Sandoval. The 28-year-old hit .279/.324/.415 this season in what was somewhat of a pedestrian offensive campaign by his standards. He's a passable defensive third baseman, a switch-hitter and would bring another jolt of contact and power to a Boston lineup that needs some punch.

Will Middlebrooks has failed to cement himself as an everyday player, and while Garin Cecchini has promise, he's not the type of player you avoid acquiring a talent like Sandoval for.

Committing four or five years to a player of Sandoval's build is certainly scary, and it’s easy to envision a scenario in which Sandoval needs to move off of the hot corner in 2018 or 2019. But he's fine there now, can transition to designated hitter or first base someday and figures to hit plenty in the interim.

The Red Sox, Yankees and Dodgers all need a third baseman, so expect the bidding for Sandoval to be high. The Giants could also make a significant play to retain their star third baseman. But with Chase Headley and Hanley Ramirez the only other strong starting options, the Sox have a good shot at acquiring Sandoval, should they so choose.

Odds of Signing with Red Sox: 33 Percent

James Shields, RHP

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In the world of MLB rumors, where there's smoke, there's generally fire. The Red Sox have been linked to Shields far too frequently in the past few months to believe their interest in the right-hander is anything but genuine.

Fans who've become aware of Shields' ironic "Big Game" moniker and who love Jon Lester may not want Shields, but they shouldn't attempt to denigrate his pitching over the past few years. Shields has posted at least 3.5 fWAR, per FanGraphs, and has thrown at least 200 innings almost every season since 2007, and he is one of the game's most consistent top-of-the-rotation starters.

The Royals are expected to make an attempt to re-sign Shields, but they don't figure to have the financial power needed to compete with the Red Sox, Yankees, Dodgers and other interested parties. As Andy McCullough of the Kansas City Star reported earlier this month, the Red Sox are seen as the prohibitive favorites to land Shields, as he should cost less than Lester or Scherzer but be similarly effective in the short term.

There are legitimate reasons not to want to sign Shields. He's already 32, his postseason track record is concerning, if not predictive, and he's never pitched in a major market, for whatever that is or isn't worth. Plus, as WEEI.com's Rob Bradford reported in September, the Red Sox don't plan on signing both Shields and Lester.

But adding Shields to their rotation would give the Red Sox a legitimate front man and would improve the club for 2015, even if he's not the man most fans and analysts want the Sox to add.

Odds of Signing with Red Sox: 40 Percent

Koji Uehara, RHP

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While much of the attention surrounding the rebuilding of the Red Sox has centered on their rotation, Boston needs to rebuild its bullpen too. Uehara and Burke Badenhop are free agents, Andrew Miller is already gone and Craig Breslow's future is in doubt, meaning the Sox could see massive turnover in what was an effective bullpen unit in 2014.

With that in mind, it makes a ton of sense for the Sox to re-sign Uehara despite his late-season struggles. Yes, Uehara gave up 10 earned runs in his final 7.2 innings and was, for all intents and purposes, shut down for most of the season's final weeks. But he held opponents to a 1.27 ERA until August 15 and looked every bit as dominant as he did during his historic 2013 run.

As WEEI.com's Alex Speier reported earlier this week, the Red Sox are engaged in talks to retain Uehara. Whether that comes from Uehara accepting a qualifying offer or the Red Sox and Uehara attempting to work out a more creative deal remains to be seen.

Whichever team signs Uehara will need to be careful about how it uses the 39-year-old moving forward, but when healthy, he should still function as a high-leverage reliever. For that reason, expect many teams to look into acquiring his services this offseason.

Still, a reunion makes a ton of sense here on too many fronts to not be considered likely.

Odds of Signing with Red Sox: 80 Percent