Ben Cherington would be smart to not spend his Benjamins on free agents featured in this slideshow.
However, there are very few about the free agents the Red Sox should NOT sign this offseason.
Boston's GM Ben Cherington enters this offseason with very deep pockets and a load of spending money to fill the numerous holes on the Red Sox roster.
There are numerous players—good and bad—in this free agent class that the Red Sox should avoid and not be tricked into signing this offseason.
Hopefully, the team does not sign a player featured in the following slideshow.
Zack Greinke could sign the most expensive contract this offseason.
Zack Greinke is the best available starting pitcher in free agency this offseason. Greinke is a 2009 Cy Young winner, only 28 years old and is still in the prime of his career.
Given that, he is going to cost a lot of Benjamins and be a long-term commitment.
That's the type of player the Red Sox should not sign right now. The Red Sox should not be looking into any expensive, long-term commitments with players after dumping two similar players in Carl Crawford and Adrian Gonzalez.
In 2012, Greinke had a 15-5 record, 3.48 ERA, 1.20 WHIP and 200 strikeouts over 212.1 innings. The ace also posted a 3-0 record, 2.11 ERA, 0.96 WHIP and .209 BAA in September.
The former sixth-overall pick has lived up to his expectations. Greinke’s career numbers include a 3.77 ERA, 1.25 WHIP and a 91-78 record, and most of those seasons were with the Kansas City Royals.
Since 2007, only once has Greinke had an ERA greater than 4.00. And since 2008, only once had Greinke not had a season with greater than 200.0 innings.
Greinke has even proved that he can pitch very well in both the American and National League, but how well can he pitch in a high-pressure, media-frenzy market like Boston?
Greinke has medical issues battling anxiety and depression, which would not bode well regularly pitching in a hostile environment like Fenway Park.
There’s no doubt that Greinke is one of the elite pitchers, but with such skills and recent success comes a hefty paycheck to acquire such an ace.
It would be hypocritical to dump hundreds of millions of dollars to make salary cap room and then invest in a pitcher for at least six years and $20 million per year.
Greinke is a great starting pitcher, but the Red Sox should look for cheaper available options that will be less of a financial commitment.
Better Expensive, Long-Term Free-Agent Starting Pitcher Option: None (unless Anibal Sanchez decreases his asking price of $90 million)
Jason Bay struggled for three years with the Mets.
Remember him? The old Red Sox player that hit 36 home runs and 119 runs batted in in 2009?
That’s the same player who hit just .165 and slugged a mere .299 with eight home runs and 20 RBI in 2012.
Jason Bay hit 41 doubles, seven triples, 26 HR, 124 RBI along with 128 runs, 231 hits and 26 stolen bases with the Mets. Those would be great numbers in a single season, which could make a great case for an MVP candidate.
However, they were spread out over three seasons and 288 games with the Mets.
The New York Mets paid Bay $48 million over the three years for his disappointing numbers and lack of playing time.
Since joining the Mets, Bay has not hit more than 20 HR or 60 RBI in a season. Also since joining the Mets, Bay has not had greater than a .260 AVG, .350 OBP and .410 SLG.
The Red Sox could take a chance by signing Bay to a one-year deal, but the team already invested in Jonny Gomes, who’s been much better in recent years.
Cheaper One-Year Deal for Available, Struggling Outfielder: Grady Sizemore (incentives included)
Aside from receiving some (deserving) postseason boos, Nick Swisher is still a fan favorite in New York.
Nick Swisher is still a solid player, who had 24 homers and 93 runs batted in last season.
However, the outfielder was a New York Yankee for the last four seasons.
Last season, Swisher hit .272 / .364 / .473 with 36 doubles, 24 homers and 93 runs batted in.
The Yankees outfielder also crushed the Red Sox in 2012, batting .459 and slugging .836 with eight doubles, five HRs, 15 RBI and 14 walks over 61 at bats against the team. Three of those home runs and 12 of those runs batted in came at Fenway Park.
But, was he really better than Cody Ross?
In 18 fewer games and 61 fewer at-bats, Ross only had two fewer doubles, two fewer HRs, 12 fewer RBI and five fewer points in batting average. However, Swisher posted an OBP (.364) 38 points higher than Ross’ (.326).
What separates the two soon-to-be 32-year-olds is that Ross, a right-handed batter, had the Green Monster in his favor, and Swisher, a switch hitter who’s better as a lefty, had the short porch in right field at Yankee Stadium in his favor.
Ross is a better fit in Fenway. Swisher is a better fit in New York.
It would certainly be controversial for the Red Sox to lure a fan favorite of the Yankees, but isn’t that exactly what the Yankees did with Johnny Damon?
Both soon-to-be 32 year olds had similar stats in 2012, but Swisher is a better fit in New York and should continue to be a Red Sox rival, not a Red Sox outfielder.
And, don't forget that Swisher was just 5-for-30 (.167) this past postseason.
Better Veteran, Free-Agent Corner Outfielder: Cody Ross
Jacoby Ellsbury is a better long-term centerfielder for the Red Sox than B.J. Upton.
The Red Sox already have a center fielder in Jacoby Ellsbury. But, if the team were to trade the 2011 AL MVP runner up, the Red Sox would need a new center fielder.
Hopefully B.J. Upton is not that center fielder.
Upton is one of the few five-tool players in baseball, but he is also one of the most disappointing players in the league.
The 2002 second-overall draft pick entered the professional level at just 19 years old. Upton has been a weapon on the basepaths, but he has not been an elite weapon at the plate.
The longtime Ray (and Devil Ray) has a career .255 AVG, .336 OBP and .422 SLG. Over the last six seasons, he’s averaged approximately 83 runs, 32 doubles, six triples, 19 homers, 71 runs batted in and 36 stolen bases per season.
Last season, Upton recorded a career-high 28 HRs, but he walked a career-low 45 times (for full seasons), struck out a career-high 169 times and earned a career-low .298 OBP. He also had a .246 AVG and .454 SLG in 2012.
Upton is one of the most talented players in the MLB, but he doesn’t play like one of them. The 28-year-old is just an average all-around player, who’s never been named an All-Star and has been criticized for his lack of hustle.
The Red Sox still need another outfielder, but hopefully it’ll be another team that overpays for the talented, yet disappointing B.J. Upton.
Side note: The same case can be made for Michael Bourn. For the Red Sox to get Upton or Bourn, Ellsbury would have to go.
Better Expensive, Long-Term Centerfield Option: Jacoby Ellsbury (pending on asking price)
Shane Victorino had his worst season at the plate in 2012.
Shane Victorino statistically had his worst full season in the majors in 2012. Still, he will certainly benefit from the thin free-agent class of corner outfielders this offseason.
Victorino posted career-low numbers in batting average, on base percentage and slugging percentage.
Last season, the soon-to-be 31-year-old hit .255 and slugged .383 with a low 72 runs, 29 doubles, seven triples, 11 homers and 55 runs batted. He had a career-high 39 stolen bases, but he also posted a career-high 80 strikeouts and a career low .704 OPS.
Not once in the 2012 season did the Hawaiian native hit greater than .290 or slugged greater than .450 in a month (excluding October, which he played three games in).
Victorino can still hit left-handed pitchers. The switch hitter hit .323 and slugged .518 against LHP, but just .230 and .332, respectively, against RHP.
However, the Red Sox already signed Jonny Gomes, who can hit southpaws and play a corner outfield position.
Former GM and current ESPN analyst Jim Bowden predicts that the two-time All-Star and three-time Gold Glove Award winner will sign for three years and close to $30 million.
The Red Sox should look else where to fill the void and let another team overpay for the declining All-Star.
Better Available Free-Agent, Corner Outfielder: Cody Ross
The Red Sox already have five catchers on their 40-Man Roster.
A.J. Pierzynski is coming off a career year at 35 years old, and he posted better numbers than the other two free agent catchers in 2012—Russell Martin and Mike Napoli.
However, the Red Sox already have five catchers on their 40-Man Roster, which include Dan Butler, Ryan Lavarnway, David Ross, Jarrod Saltalamacchia and Christian Vazquez.
In 2012, Pierzynski hit .278 / .326 / .501 with 18 doubles, 27 homers and 77 RBI. He posted career-high numbers in HRs, RBI, SLG and OPS.
The Red Sox already have a surplus of catchers on their roster. If the team looks to add a catcher, he should be a part-time catcher who can play other full-time positions too, like first base.
But, Pierzynski is a full-time catcher the Red Sox should avoid. Instead of adding another catcher, the Red Sox will likely dump one this offseason (Salty or Lavarnway).
Side note: Look for the Yankees to look into Pierzynski, a left-handed power hitter who would love to play in a stadium with a short porch in right field.
Better Free Agent Catcher Option: Mike Napoli (as a second- or third-string catcher)
Ryan Dempster got shelled in his last start with the Rangers in 2012.
It’s very difficult to predict the type of year Ryan Dempster will have. He could be a starter one year and a closer another. He could have a three ERA one year and a five ERA the next.
If one thing is for sure, Dempster is a better NL pitcher and cannot pitch against the better hitting AL teams.
In 2012, the longtime National League pitcher was traded from the Chicago Cubs to the Texas Rangers. The Rangers hoped the 35-year-old could have been a key addition to their run for a third World Series appearance, but he and the team failed to win big games and missed the playoffs.
Dempster had a 12-8 record and a 3.38 ERA in 2012. With the Cubs he was 5-5 with an impressive 2.25 ERA, and with the Rangers he was 7-3 with a disappointing 5.09 ERA.
However, the real stat line for Dempster is his struggles against better teams.
The righty was 9-2 with a 1.98 ERA against teams with losing records and 3-6 with a 4.65 ERA against teams with .500 or winning records last season.
Dempster’s most important start of the year came against the Athletics in the last game and series of the season. He allowed six hits, five runs and a walk over just 3.0 innings. The Rangers lost that night, relinquished the division to the A’s and then folded in the AL Wild Card game.
It would be a big risk for an AL team to sign Dempster, unless they have him as a spot starter against teams with losing records. He belongs in the NL, the worse hitting half of the MLB, and not in the very competitive AL East.
Cheaper Veteran, Free-Agent Starting Pitcher Option: Erik Bedard (Part II)
Edwin Jackson has a career record of 70-71 with a 4.40 ERA.
The most impressive stat line for Edwin Jackson is that he’s pitched more than 180.0 innings in each of the last five seasons, including three 200-plus inning seasons. The least impressive stat line for the highly-touted free agent is that over his 10-year-career only twice has he had an ERA below 4.00 at season's end.
Aside from his rookie season, which included only four appearances, Jackson has also never had an ERA of sub-3.50 at season’s end either.
The 29-year-old has a career record of 70-71 with a 4.40 ERA, 1.44 WHIP and .271 BAA. And last season, his stats weren’t flashy either.
In 31 starts in 2012, Jackson posted a 10-11 record with a 4.03 ERA, 1.22 WHIP, .243 BAA, 168 strikeouts and 23 homers allowed.
In last year’s NLDS, Jackson went 0-1 in his only start, allowing eight hits, four earned runs, one walk and a homer over just 5.0 innings. He also allowed one hit, one run and two walks in his one relief appearance, as well.
In the 2011 playoffs, the former Cardinal posted a 1-1 record with a 5.60 ERA and 1.58 WHIP over four starts. Jackson earned the loss in his lone World Series start, allowing three hits, three runs and seven walks over 5.1 innings.
Yes, seven walks.
Speaking of walks, in Jackson’s no hitter, which he tossed in 2010 with the Rays, he walked eight batters. It also took him 149 pitches to complete the no hitter.
Jackson is a player that a team will likely overpay this offseason and hopefully the Boston Red Sox are not crazy enough to do so.
Better Long-Term, Free-Agent Starting Pitching Option: Anibal Sanchez
Stephen Drew has only been average since his rookie season.
The 2004 first-round draft pick made a name for himself in his first MLB call-up in 2006.
Since then, the once 23-year-old phenom has only played like an average and injury-plagued shortstop.
In the 2006 season, Stephen Drew hit .316 and slugged .517 with 13 doubles, seven triples, five homers and 23 runs batted in over just 59 games.
However, the once promising Diamondbacks shortstop has not lived up to his high expectations since his rookie season.
From 2007 to 2012, Drew has not finished the season with a .300 batting average and only once with a .500 slugging percentage or greater. During that span, the former first-round pick has batted just .262.
Over his first four seasons in the MLB, the shortstop averaged 147 games, 76.25 runs, 33.5 doubles, 9.75 triples, 15 HRs and 53 RBI. However, from 2011 to 2012, Drew has played a total of just 165 games.
Stephen Drew has played no more than 86 games in each of the last two seasons.
And, for four seasons before his injury streak, the shortstop was only an average hitter.
In favor of Drew, he is the biggest free agent shortstop among the short list of available shortstops this offseason. Given that, his asking price will be too high for his value because of the thin class at his position.
Aside from an impressive rookie season, Drew has only been a mediocre shortstop over his career, and he is a player the Red Sox should avoid this offseason.
Better Shortstop Free-Agent Option: Marco Scutaro
Don't even think about it, Ben Cherington.
Do I really need to elaborate on why it would be crazy for the Red Sox to bring back Daisuke Matsuzaka?
He's one of, if not, the worst signing by the Red Sox in recent years.
Better Free-Agent Starting Pitcher Option: Anyone not named Daisuke Matsuzaka, who posted a 1-7 record, an 8.28 ERA and a 1.71 WHIP in 2012.