Top ten free agents the Red Sox could pursue this offseason

In this BoSox Injection slideshow, we take a look at the top ten free agents that the Red Sox may plan on pursuing this winter. While the team is currently in the midst of a rough 2014 season, the future offers hope and the Red Sox reportedly plan on being right back in the race next season. Therefore, we could have a big offseason on our hands. Let’s take a look at which free agents the Red Sox may be shopping for this offseason.

Luke Gregerson, RP

The bullpen hasn’t been a major area of need even in a rough 2014 season, but after trading Andrew Miller at the Trade Deadline, the Red Sox could still look to revamp their ‘pen in the offseason. Gregerson is an elite setup man and has had a great year in his first season with the Oakland Athletics, posting a 2.26 ERA and 3.83 K/BB in 55 appearances. Gregerson, along with Junichi Tazawa, would give the Red Sox two top-notch setup men as they look to contend.

The Red Sox don’t have much money committed towards the future; thus, they could easily afford a contract in the range of a 3 year/$20M deal. That’s big money for a non-closer relief pitcher but Gregerson is as deserving as they come. The highest ERA that he has ever posted is 3.24 in his rookie season and, aside from an outlying 2013 season in which he had a 2.71 ERA (terrible, right?), his ERA has lowered every season of his Major League career. At 30 years old, he should stay effective for several more years, and the Red Sox would be right to let him continue his success in Boston.

Chase Headley, 3B

Should the Red Sox look to supplement their lineup this offseason, and they certainly should, then third base is likely their weakest position from an offensive standpoint. Will Middlebrooks is still yet to prove himself as an MLB regular and Brock Holt has slowed down of late, slashing just .212/.271/.263 since the All-Star break, leaving definite room for improvement at the hot corner.

Chase Headley would not be a big-name addition at third base, but he could be a good buy-low candidate for the Red Sox that could really help the team on offense and defense. He is currently in the midst of the worst season of his career, slashing .234/.308/.359 overall, but he has been better in 20 games since being traded to the Yankees. In 83 plate appearances in New York, his line has improved to .250/.349/.375 along with his trademark excellent defense which could make Headley a valuable addition for 2015. He would be an unspectacular addition for the Red Sox but he’s a realistic candidate to come to Boston and produce on a cheap, short-term deal.

Aug 12, 2014; Kansas City, MO, USA; Oakland Athletics starting pitcher

(31) delivers a pitch in the first inning against the Kansas City Royals at Kauffman Stadium. Mandatory Credit: John Rieger-USA TODAY Sports

Jon Lester, SP

No surprise here. Fans have been clamoring for the Red Sox to trade Lester and then re-sign him in the offseason since well before the left-hander was even traded, but I’ll still add my two cents to the mix.

Lester is one of the best arms in Red Sox history and was in the midst of having a career year before being traded to the Oakland Athletics where he has shown more of the same. Between the Red Sox and A’s this season, Lester’s ERA stands at a career-best 2.51 and his 4.57 K/BB is by far the best of his career as well.

He fills an obvious role in the organization, as he’d be filling the very ace role vacated after the Red Sox traded him, and he is also familiar and enamored with the city of Boston and its fans. There’s no guarantee that Lester will return to the Red Sox, but a deal with him is more likely than a deal with any other top pitcher on the market and the Red Sox certainly need a top pitcher in order to contend.

Aug 9, 2014; Kansas City, MO, USA; San Francisco Giants third baseman

(48) at bat in the ninth inning against the Kansas City Royals at Kauffman Stadium. The Royals won 5-0. Mandatory Credit: Denny Medley-USA TODAY Sports

Pablo Sandoval, 3B

Sandoval would be the most expensive offensive player on this list but if the Red Sox are looking to improve their offense in a big way, then there are few better options than the fun-loving Kung Fu Panda. Barring a very strong finish from Will Middlebrooks, third base must be viewed as an area of weakness for the Red Sox, and Sandoval would be a huge upgrade at the hot corner.

Since reaching the Major Leagues with the Giants in 2008, Sandoval has been one of the best offensive third basemen in the league. His career slash line stands at .295/.347/.469, especially impressive considering that he has spent his entire career in a pitchers’ park. Sandoval is currently in the midst of a .280/.326/.431 in San Francisco and he has added 14 home runs to the Giants’ lackluster offensive attack. It’s easy to imagine the switch-hitter improving significantly in Boston as the spacious right field in Fenway Park would add doubles from the left side and the green monster would add more doubles as well as some home runs from the right side.

At 28 years old, Sandoval is young enough to potentially prove his worth over a relatively long deal. Considering his weight, however, (Sandoval stands 5’11” at 245 pounds) he could decline quickly once he passes his prime. I would be hesitant to offer a deal longer than five years, but a contract offer of something around 5 years/$90M could likely bring Sandoval to Boston and add quite a bit of power to the Red Sox lineup.

Aug 8, 2014; Atlanta, GA, USA; Atlanta Braves starting pitcher

(30) throws a pitch against the Washington Nationals in the second inning at Turner Field. Mandatory Credit: Brett Davis-USA TODAY Sports

Ervin Santana, SP

If the Red Sox miss out on some of the big pitchers on the market like Lester or Shields, or if they’re simply trying to add depth to their starting five, then Santana could be an interesting addition. Santana is having a great year in his first season in Atlanta, posting a 3.66 ERA which is backed by an even-better 3.13 FIP and a 3.04 K/BB.

There are concerns with bringing Santana to Boston; first and foremost, he has been a fly ball pitcher throughout his career. However, with Santana’s good command and solid strikeout numbers, the occasional home run is not quite as devastating. Still, that issue could prevent the Red Sox from paying top dollar for Santana. He will be 32 years old to start next season and could be in the market for a four-year contract, which may be a bit of an overpay. However, if the Red Sox could shorten it to a three-year deal worth something in the range of $55M, then Santana could be on the Red Sox next season.

While Santana is an interesting name, though, don’t expect the Red Sox to seriously pursue him unless they miss on both Lester and Shields.

Aug 14, 2014; Kansas City, MO, USA; Kansas City Royals pitcher

(33) delivers a pitch against the Oakland Athletics during the first inning at Kauffman Stadium. Mandatory Credit: Peter G. Aiken-USA TODAY Sports

James Shields, SP

While we’re on the topic of top starting pitchers, we might as well spend some time talking about Shields. Shields, the third-best pitcher on the free agent market behind Jon Lester and Max Scherzer (who is likely out of Boston’s price range), could be an interesting option for the Red Sox if they miss out on Lester.

Shields has been a consistently solid pitcher for the better part of the last decade, after breaking into the majors with the Tampa Bay Rays in 2006, and he’s as known a quantity as they come. He is having a typical Shields season in 2014, posting a 3.29 ERA with a 3.91 K/BB, and profiles as a solid #2 starter for any team.

The one major concern for Shields is his age as he is currently 32 years old but could still be in the market for a longterm deal this offseason. However, the Red Sox could likely sign him to a similar contract to Santana: somewhere in the 3 year/$60M range or perhaps 4 years/$75M. If the Red Sox miss on Lester, though, Shields is their best bet to acquire a top-flight starter.

Aug 3, 2014; St. Louis, MO, USA; Milwaukee Brewers third baseman

(16) hits a one run single off of St. Louis Cardinals starting pitcher

(not pictured) during the first inning at Busch Stadium. Mandatory Credit: Jeff Curry-USA TODAY Sports

Aramis Ramirez, 3B

Ramirez offers something in between Headley and Sandoval, the two previous third base targets I’ve mentioned. Being 36 years old, he won’t be in the market for a longterm contract, similar to Headley, but he also has been a consistent performer and the Red Sox would likely get their money’s worth if he’s able to stay healthy, similar to Sandoval.

Ramirez is as solid and consistent a performer as there is in Major League Baseball, as his OPS+ has been at or above 102 in ten of the last eleven seasons. Even at age 36, he’s having a productive season for the Brewers, slashing .299/.340/.454 with 13 home runs in 96 games. There are a few concerns over his 2014 performance, primarily regarding his plate discipline as his 3.9% walk rate is the least he has walked since 2000 and his BABIP of .322 is well above his career average of .293.

However, Ramirez doesn’t need to hit .300 (he’s batting .299 this season) to be a very effective third baseman. His right-handed power would play well in Fenway Park and, as he’ll be 37 on Opening Day next year, the Red Sox could likely pick him up on a one or two year deal. Something in the range of 2 years/$20M would likely net Ramirez and land the Red Sox a quality third baseman and middle-of-the-order hitter.

Jul 9, 2014; Cleveland, OH, USA; New York Yankees relief pitcher

(30) delivers a pitch in the 14th inning against the Cleveland Indians at Progressive Field. Mandatory Credit: David Richard-USA TODAY Sports

David Robertson, RP

Robertson will be the premier closer available on the free agent market this winter and, if the Red Sox are unable to re-sign Uehara, then he could be a target for Boston. The longtime Yankee reliever has excelled since taking over for the retired Mariano Rivera, shutting down the opposition to the tune of a 2.62 ERA, supported by an even better 1.97 FIP, with an Andrew Miller-esque 14.3 K/9 this season.

In just his first season as a full-time closer, Robertson has already entered elite status and, at just 29 years old, could command a hefty contract this offseason. However, he is still a relief pitcher and won’t likely command more than something in the range of 4 years/$40M. However, considering the volatility of relief pitchers, that may be out of the Red Sox price range. As good as Robertson is, don’t expect the Red Sox to seriously consider him unless they are unable to retain Uehara.

Aug 12, 2014; Cincinnati, OH, USA; Boston Red Sox relief pitcher

(19) pitches during the ninth inning against the Cincinnati Reds at Great American Ball Park. The Red Sox defeated the Reds 3-2. Mandatory Credit: Frank Victores-USA TODAY Sports

Koji Uehara, RP

Of course, there’s still a pretty good chance that the Red Sox do wind up keeping Uehara. The 39 year old’s performance has only dropped slightly from his otherworldly 2013 season, as he has once again been one of the best closers in baseball. While his FIP of 2.41 suggests that he may have gotten a bit lucky this season, his ERA is still incredible at 1.27 and his K/BB of 10.0 is once again phenomenal.

If he was a few years younger, Uehara would likely be able to sign a longterm, expensive deal. However, at 39, he’ll likely just sign a one-year deal despite his elite performance over the past two seasons with the Red Sox. In fact, it’s pretty likely that Uehara would simply accept a qualifying offer if the Red Sox decide to go down that route. Uehara is a cheap option who has been incredibly successful in Boston and it’s relatively likely that he’ll be the Red Sox closer again come 2015.