Here's a look at five key positions the Red Sox must address this winter and some of the likely free-agent candidates Cherington could pursue:
Starting pitching: Two spots to fill
More than any other position, it was the starting pitching that failed Boston down the stretch, posting a 7.08 ERA in September. Already a key concern going into the offseason, the situation is further clouded with the announcement that John Lackey will miss the 2012 season following Tommy John surgery.
With Daisuke Matsuzaka also expected to miss significant time in 2012, the Red Sox enter the season with about $26.3 million committed to injured starters.
Alfredo Aceves could get a shot at one of the two openings in the rotation. He was one of the team's most valuable pitchers in 2011, posting a 2.61 ERA and shining down the stretch (1 ER in final 16 IP). Aceves struggled in the small sample size of four starts (5.14 ERA), but could get an extended look given the current lack of options.
Given the dollars committed to injured starters, it's no surprise to hear Cherington will be on the lookout for bargains.
"We need to add some pitching depth," Cherington said Tuesday at his introductory press conference. "I think most likely we'll do that through some good creative, perhaps buy-low acquisitions. We're going to do our diligence on every available player. But I think we need to hit on some pitchers this offseason in much the same way we did with Alfredo Aceves last offseason."
That could mean a long winter search. Aceves wasn't non-tendered by the New York Yankees until December, and the Red Sox signed him in February.
Big name options -- C.J. Wilson and potentially CC Sabathia -- appear unlikely. Wilson raises some red flags given his control issues. Since 2010, his 167 walks are fourth-most in the majors. If Japanese pitcher Yu Darvish is posted, he'll garner significant interest. It remains to be seen if Boston will be gun-shy following the Matsuzaka investment. Darvish went 18-6 with a 1.44 ERA for the Nippon Ham Fighters in 2011. Those numbers are even more impressive than Daisuke's final season in Japan: 17-5, 2.13 ERA.
Also keep an eye on Hisashi Iwakuma (6-7, 2.42 ERA in Japan). At 30, he's five years older than Darvish and not nearly on his level as a strikeout pitcher, but will come significantly cheaper.
The next tier of starters includes Mark Buehrle, who would provide durability for a rotation overcome with injuries. His streak of 11 straight 200-inning seasons is the longest for an AL pitcher since Mickey Lolich (1964-75). Roy Oswalt, a far less durable option, appears more likely to remain in the NL.
Cherington's bargain hunting could take a page from the Yankees' success with Bartolo Colon and Freddy Garcia in 2011 (both are again free agents). Chris Capuano's name could come back up. The Red Sox reportedly flirted with a late-season acquisition of Capuano. He'd come at a low price, and his 3.67 xFIP was far lower than his 4.55 ERA. Others to consider: Bruce Chen, Aaron Cook, Jeff Francis and Rich Harden.
Relief pitching: Market rich on closers, thin on set-up
Papelbon's bounce-back season stopped a downward trend in his career. If the Red Sox were planning to let him walk after the season, that no longer appears to be the case. The new regime appears to placed his return as a priority.
"We have talent in the bullpen," Cherington said. "Obviously with Papelbon not knowing the outcome of that, of Pap's decision, we potentially have an opening at closer. We have a couple people, players in-house that we think are capable of filling that role if needed."
The obvious in-house candidate would be Daniel Bard. Despite his 10.64 ERA in September, Bard's full body of work was still impressive. Opponents hit just .179 and have averaged more than a strikeout per inning.
Particularly with the possibility of Aceves in the rotation, the Red Sox might not be able to afford to move Bard out of his current role even if Papelbon departs. Closers abound on the free agent market, but the set-up candidates come with question marks.
The Red Sox hold a $3 million option on Dan Wheeler for next season. He pitched in low-leverage situations for much of 2011, but proved mostly effective. From May through August, Wheeler posted a 2.72 ERA in 34 appearances.
Shortstop: Scutaro is back, but is he the answer?
Few Red Sox made a positive impression in September, but Marco Scutaro was an exception. He hit .387 in the final month of the season, third best in the American League. Over the last 10 years, only Manny Ramirez (.396 in 2002) and David Ortiz (.396 in 2007) have posted a higher September average for Boston.
The strong final month gave Scutaro a .781 OPS that rivaled his final season in Toronto. Indeed, after a disappointing first year, he played up to his contract in 2011.
The Red Sox exercized their a $6 million team option on Scutaro on Sunday, which also happened to be his 36th birthday.
"Scutaro had a really good year and we believe he'd be very coveted this offseason if he got into the market," Cherington said in his introductory press conference.
That said, intriguing free agent options could make him relegated to the utility role to which he's so well-suited. Could Cherington secure the position that haunted Theo Epstein throughout his tenure as general manager?
Jose Reyes would certainly qualify as a splash. Offensively, Reyes is clearly at the top tier of shortstops -- his .386 weighted on-base average (wOBA) ranked second in the majors to Troy Tulowitzki. However, concerns remain about his defense. His minus-11 defensive runs saved in 2011 were third-worst among shortstops. Reyes will require a massive contract, money the Red Sox may need to devote elsewhere.
Jimmy Rollins is the other top-level option if Boston decides to go in a new direction. Since winning the MVP in 2007, Rollins hasn't achieved the same level of production. In the four years since, he has a .261 BA and .737 OPS. In that same span, Scutaro has a .280 BA and .745 OPS. Rollins is reportedly seeking a five-year deal, a major commitment for a shortstop about to turn 33.
The rest of the free agent class is relatively thin. Rafael Furcal (assuming his option isn't picked up) has averaged 92 games per season since 2008, an alarming number for a team that hasn't been able to stay healthy for a full season the last couple of years. Meanwhile, Clint Barmes and Alex Gonzalez are solid defensive options with questionable bats.
Right field: Opportunity for an upgrade
The end of the J.D. Drew era provides the biggest opportunity for an offensive upgrade this offseason. Appearing in just half of Boston's games, Drew hit .222 with a .617 OPS. Red Sox right fielders finished last in the majors in batting average (.233), OBP (.299) and led only the Seattle Mariners in slugging percentage (.353).
Boston seems likely to pursue a more proven a more proven option, particularly if he's a right-handed bat that can balance the lineup.
Based on 2011 performance, Carlos Beltran is the cream of the free-agent crop. After back-to-back injury-plagued seasons, he rebounded in 2011 to hit .300 with a .920 OPS. His 4.7 WAR placed him among the top 10 NL outfielders. As an added bonus, Beltran won't cost his future team any draft picks due to a contract stipulation that prevents arbitration. Soon to turn 35, his durability is still a major concern.
Michael Cuddyer broke through in Minnesota back when Big Papi was still in town, and has been a solid, if unspectacular contributor since. Like most Twins, he faltered late in 2011, posting a .691 OPS after Aug. 1. He still managed an .805 OPS on the season, and would particularly be an asset against left-handers (.869 career OPS). He's expected to be a Type-A free agent, which could give pause to potential suitors, as signing him would require surrendering a high draft pick.
With 29 home runs and .810 OPS for the Oakland A's, Josh Willingham continued to produce at a consistent level. Only two outfielders have posted an OPS over .800 in each of the past six seasons: Willingham and Matt Holliday. Though right-handed, he hit just .208 against southpaws last season.
A potential wild card candidate: Grady Sizemore. The Cleveland Indians hold an $8.5 million club option with a $500K buyout. Still just 29, Sizemore hasn't stayed healthy since his 30-30 year in 2008.
Designated hitter: Not many viable options beyond Ortiz
David Ortiz has been the exception to decreased production at designated hitter, putting together in 2011 his best season since 2007. His .953 OPS was over 100 points higher than the next eligible DH (Victor Martinez). Billy Butler's 19 home runs were second most at the position, but fell 10 short of Big Papi's 29.
The going rate for designated hitters has seen a market correction in recent years. After hitting .300 with an .841 OPS in 2010, Vladimir Guerrero couldn't do better than a one-year contract for $8 million. Ortiz likely won't have to settle for a one-year deal.
The Red Sox already appear to prioritizing his return, in part due to a lack of viable alternatives who can match his production. Prized free agents Prince Fielder and Albert Pujols are the only potential offensive upgrades. While Epstein may be trying to procure Thanksgiving invites from either, neither figure to be realistic options for Boston.
Realistic replacements for Ortiz are far less intriguing. In fact, it's largely the same list from last offseason (if the team doesn't look internally). Johnny Damon (.743 OPS), Guerrero (.733) and Hideki Matsui (.696) are all coming off one-year contracts and will be at least 37 years old. Of the three, Damon (just 277 hits shy of 3,000) would seem the best fit. Though struggling at home, Damon posted an .807 OPS on the road and has proven success at Fenway.
Jason Kubel could be a potential buy-low option. Nine years ago, Epstein struck gold with a DH castaway from the Minnesota Twins. That may be where the comparison with Ortiz ends, but Kubel has a strong track record and is just 29. He's suffered from playing at Target Field, which has played a part in preventing a repeat of his .907 OPS in 2009.
Jeremy Lundblad is a senior researcher with ESPN Stats & Information. He provides statistical analysis for ESPNBoston.com.