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10 Ways the Boston Red Sox Should Manage Their Newfound Riches

Zachary D. RymerMLB Lead WriterApril 24, 2015

10 Ways the Boston Red Sox Should Manage Their Newfound Riches

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    Thanks to the trade that sent Josh Beckett, Carl Crawford, Adrian Gonzalez and Nick Punto to the Los Angeles Dodgers last week, the Boston Red Sox find themselves $250 million richer.

    Time to make it rain this offseason, right?

    Probably not, actually. The Red Sox have a ton of money to spend now that three of their most bloated contracts are off the books, but general manager Ben Cherington hit the nail on the head when he told WEEI (via that the amount of money he has to play with is no excuse to be reckless:

    "It will be exciting to find ways to complement that core of talent (we currently have). We've got to be smart in doing it. We can't just go and try to fill the void in one or two fell swoops. We've got to try to build a team and do it in a smart way and do it in a way that reflects what we believe in."

    Being smart involves making smart investments, sure, but it also means avoiding dumb investments. Such is what I know about business, anyway. And after what the Red Sox have been through in recent years, one assumes that Cherington and his staff know this as well as anyone.

    So what moves should the Red Sox make this winter? Just as important, what moves shouldn't they make?

    That's what we're here to discuss, starting with the moves the club shouldn't make.

    Note: Stats and salary info come from unless otherwise noted.

Don't Go There: Josh Hamilton

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    With Beckett, Crawford and Gonzalez off the books, the Red Sox can afford to make a run at Josh Hamilton this offseason.

    Hamilton is hitting .292/.355/.582 this season with 35 home runs and 111 RBI, and he would seem to be a perfect candidate to fill the vacancy in left field opened up by Crawford's departure, not to mention the hole in Boston's lineup left by Gonzalez's departure.

    ...But not many. Pursuing Hamilton this winter is high in the running on the list of the worst possible ways for the Red Sox to spend their new riches.

    The Red Sox are a mess these days largely because of reckless signings they've made in the last few years. Crawford's contract and Beckett's extension come to mind, as does John Lackey's contract (too bad the Dodgers couldn't take that one off Boston's hands too). Going forward, the last thing they want to do is make more reckless signings.

    There's the rub. Signing Hamilton to a contract would be the ultimate reckless signing.

    In all likelihood, Hamilton is going to command a contract worth somewhere around $20 million per anum. That tends to be the going rate for perennial 100-RBI men with 40-homer power. 

    The issue is that he's as unreliable as they come both on and off the field. On the field, he's prone to injuries and long slumps (see June-July this season, the second half of 2008, April-May of 2010, etc.). Off the field, his past issues with drug and alcohol abuse make him one of the most high-maintenance players in the league (not a knock, just a fact).

    Plus, he's already 31 and will be 32 next May. He's almost at that age where hitters tend to start declining.

    Hamilton will get the kind of contract he wants. He just shouldn't get it from the Red Sox.

Don't Go There: Zack Greinke

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    The Red Sox lost a lot of offense in trading away Crawford and Gonzalez. Finding a way to make up for their production is going to be one of Cherington's top priorities this offseason.

    But offense isn't Boston's main problem, and it really hasn't been a problem for a couple years now. The Red Sox finished second in the AL in runs scored in 2010, first in 2011, and are currently ranked second this season.

    Pitching is Boston's main problem, specifically starting pitching. Sox starters had a 4.17 ERA in 2010, a 4.49 ERA in 2011 and they have a 4.85 ERA this season. 

    Clay Buchholz looks like he's going to be the team's ace going forward, but behind him the Red Sox are likely going to have a broken-down version of Jon Lester, a youngster in Felix Doubront and an albatross in John Lackey. Finding at least one rotation upgrade this winter is a must.

    Just as Hamilton will be the top hitter on the market this winter, Zack Greinke will be the top pitcher. The Red Sox can afford Hamilton, and they can afford Greinke too.

    But also just like Hamilton, Greinke would represent a reckless signing for the Red Sox. They need to steer as clear of him as they possibly can.

    This is not to suggest that Greinke is a bad or overrated (a word we probably toss around too much) pitcher. According to FanGraphs, he ranks sixth among all pitchers in WAR since 2009 and fifth in Fielding Independent Pitching at 2.91. He has exactly the kind of numbers that support a demand for a $100-plus million contract like the one from the Milwaukee Brewers that he supposedly turned down.

    That's a lot of money to pay for a guy whose return to the American League this season has resulted in a 5.22 ERA in six starts. And as far as the Red Sox should be concerned, that's a lot of money to pay for a guy who has an ERA over 6.00 in his career against the Yankees.

    Greinke's personality is also less than an ideal fit for Boston, where the fans are intense and unforgiving and the media scrutiny can get to be exhausting (as Nomar Garciaparra told me last week).

    I have my doubts about whether Greinke is even open to signing in Boston. For their part, the Red Sox should be just as skeptical about a potential partnership.

Don't Go There: Nick Swisher

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    I get the sense that I'm in the minority here, but I actually like Nick Swisher as a player. Sports Illustrated would have us all believe that he's one of baseball's most overrated (there's that word again) players, but there are only four right fielders with higher WARs than Swisher since 2009, according to FanGraphs.

    The problem is that Swisher apparently sees himself as a superstar rather than a solid complementary players, and we have Jayson Werth to thank for that.

    According to Jon Heyman of, Swisher is going to be looking for a deal similar to the seven-year, $126 million contract Werth signed with the Washington Nationals before the 2011 season.

    Will he actually get that kind of money?

    Yeah, I think so. He has numbers comparable to Werth's when he became a free agent following the 2010 season, and his numbers are only getting better thanks to his recent hot stretch.

    But will he get that kind of money from the Red Sox?

    For their sake, I hope not. Signing Swisher to a Werth-like deal would make the J.D. Drew signing look like a bargain, and that's not a compliment.

    The Red Sox are better off shying away from Swisher and letting some other team throw money at him.

Other Don't Go There's

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    Melky Cabrera

    He cheated his way to a .346 batting average and an MLB-best 159 hits before he got suspended for testosterone use. That's a pretty big red flag. Another big one is the fact that character concerns have followed Cabrera wherever he's gone. He'd be a solid, cheap option for the Red Sox in left field, but he simply brings too much baggage to the table.

    Ryan Dempster

    Dempster has an ERA of 5.46 in five starts for the Rangers since coming over in a deal at the trade deadline, thus confirming the widespread theory that he's a horrible fit for the American League. He'd be a low-risk signing, but a low-reward one too.

    Francisco Liriano

    Liriano is still young and still has good stuff, but he's about as reliable as bulletproof vest made of Swiss cheese. He'd be another low-risk, low-reward signing.

    Delmon Young

    Young is yet another outfielder with character red flags, and he tends to only hit well in spurts. In addition, he's a huge defensive liability.

Re-Sign Cody Ross

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    Cody Ross is a lot like The Dude. He's the man for his time in place. He fits right in there.

    More to the point: The Red Sox aren't going to find a right-handed hitter with a more perfect swing for Fenway Park than Ross. He was born to play in Boston.

    Ross is having a solid season, as he's hitting .281/.343/.522 with 19 homers and 61 RBI in 98 games. But if the Red Sox played all their games at home, Ross would be a .316/.371/.617 hitter. That's how good he's been at Fenway this season.

    Ross is playing on a one-year deal worth a mere $3 million, but Gordon Edes of has already reported that the Red Sox want him back and that an extension could be hammered out before the end of the season.

    If something can't be done before the end of the season, the Red Sox need to move as quickly as they can to make sure Ross comes back in 2013 and beyond. I'm thinking a three-year deal worth around $7 or $8 million a season, similar to what Josh Willingham got from the Twins, would be perfect.

    The Red Sox should obviously stop short of offering Ross a blank check, but he simply needs be back in a Red Sox uniform next season.

Extend Jarrod Saltalamacchia

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    Jarrod Saltalamacchia has his shortcomings. He strikes out a ton, and he's no Ivan Rodriguez behind the plate.

    But for the money the Red Sox have paid him over the last two seasons, Saltalamacchia has been a steal. Better yet, he's still young at 27 years old and he's getting a little bit better as a player as time goes by. He already has a career-high 21 home runs this season, 17 of which came before the All-Star break.

    Brian McPherson of the Providence Journal wrote all the way back in May that it "wouldn't be surprising" if the Red Sox signed Salty to an extension, and the man himself said he was very much open to signing on with Boston long term.

    "I love it here," he said. "I feel comfortable. This park, I really like it because I can do what I like to do - hit the ball to left, pull if I need to. The guys here, the organization, they've been really great to me, and I don't want it any other way. When you're happy, you seem to play a little better."

    Saltalamacchia is making $2.5 million this season. An extension would have to pay him a lot more than that on an annual basis. No doubt Salty's reps would point to the five-year, $60 million extension Miguel Montero signed with the Arizona Diamondbacks earlier this season as a starting point. 

    My best guess is that Salty could probably be locked up for something more like $10 million per year for around five years. A contract like that wouldn't be a steal, but it's the kind of contract that should end up being fair for both sides if Salty stays on the path he's put himself on since arriving in Boston in 2010.

    Since the Sox can spare the cash, they should carve out a deal like that with Salty if they can.

Try to Extend Jacoby Ellsbury

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    Re-signing Ross should be easy. Extending Saltalamacchia likely won't be too difficult.

    But extending Jacoby Ellsbury? Yeah, that will be difficult.

    There are two problems with the notion of the Red Sox signing Ellsbury to an extension.

    First and foremost, Ellsbury is represented by renowned cash hound Scott Boras. He doesn't do extensions. He does free agency, and Ellsbury is just one year away from free agency.

    Second, Ellsbury may not be willing to accept a low-ball offer just because he's coming off a disappointing 2012 season. The Red Sox will probably try to sign him to an extension worth somewhere between $10 and $15 million per year, but both Ellsbury and Boras know full well that a $20 million per year contract could be had if Ellsbury performs in 2013 like he did in 2011.

    But should the Red Sox at least try to sign Ellsbury to an extension this offseason? Sure, there's no harm in trying.

    And besides, the word from Nick Cafardo of The Boston Globe is that Ellsbury may not be as desperate to leave Boston as some think he is. On the contrary, a team source told Cafardo that Ellsbury wants to stay.

    Boras probably wants Ellsbury to explore the open market after 2013, but it's ultimately Ellsbury's call. If he gets an offer to his liking from the Red Sox, he could overrule his agent.

    If he shows no signs of being willing to accept anything, the best thing for the Red Sox to do will be to trade Ellsbury. This winter will be the time for them to get what they can for Ellsbury if they fail to sign him to an extension.

Sign Brandon McCarthy

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    Beyond Zack Greinke, the 2013 free-agent class of starting pitchers is pretty thin on talent. Unless the Chicago White Sox decline to pick up Jake Peavy's $22 million option, Greinke is going to be the only true No. 1 starting pitcher on the market.

    There will, however, be plenty of solid No. 2 and No. 3-type starting pitchers who won't command contracts with lots of zeros. It's these pitchers that the Red Sox should be interested in.

    Names that come to mind are pitchers like Anibal Sanchez, Edwin Jackson, Kyle Lohse, Shaun Marcum and possibly Ervin Santana if the Angels choose to cut him loose.

    But the pitcher who makes the most sense for the Red Sox is Brandon McCarthy. 

    McCarthy has one major red flag to his name, and that's that he's injury prone. He's battled shoulder injuries throughout much of his career, and he also dealt with elbow problems in 2008. His medical file is about as thick as the collected works of Stephen King.

    The good news: This will keep McCarthy's price relatively low. He could be had on a one or two-year deal with a modest base and a ton of incentives.

    If so, he'd actually represent a low-risk signing. The beauty of it is that he'd also be a high-reward signing.

    When McCarthy has pitched in the last two seasons, he's been very good. He has a 3.18 FIP since the start of the 2011 season, according to FanGraphs, and that actually ranks him ahead of pitchers such as Johnny Cueto, David Price and Cole Hamels.

    Plus, one just gets the sense that his personality would be a good fit for Boston's clubhouse. Anyone who follows him on Twitter can vouch that McCarthy doesn't take himself too seriously.

Sign Mike Napoli

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    If you can't beat 'em, sign 'em.

    You have to figure it was a line of thinking such as this that led the Red Sox to sign Carl Crawford in 2010. If they get a notion such as this in their heads again, it will invariably lead them to Mike Napoli.

    Napoli has killed the Red Sox during his career, battering them around to the tune of a 1.075 OPS and 15 home runs in just 38 games. He has a 1.107 OPS and seven career home runs against the Red Sox at Fenway Park.

    Napoli could be a solution at first base for the Red Sox if they choose not to re-sign James Loney (as they should). And as Matthew Leach of suggested, Napoli could basically be used by the Red Sox the same way the Rangers have used him in the last two seasons: as a sort of catcher/first baseman hybrid.

    There are certain dilemmas when it comes to the idea of signing Napoli, to be sure. Signing him would overload the Red Sox's lineup with right-handed hitters, and it's concerning that he'll be coming off a highly disappointing 2012 season with the Rangers.

    On the bright side, that will lower his price, meaning his situation would be completely different than that of Crawford. Napoli could even be willing to accept a one-year deal in which to prove himself, sort of like what Adrian Beltre did in 2010.

    A one-year deal with Napoli would be just fine as far as the Red Sox are concerned, as it would give them a chance to take advantage of a 2014 free-agent class that could include Justin Morneau, Kendrys Morales and Mike Morse.

    Or the Red Sox could go all in on Napoli with a multi-year contract and hope for the best. He's the kind of guy who's worth the risk.

Re-Sign David Ortiz...But Only If It Can Be Done for 1 Year

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    The biggest unknown regarding Boston's upcoming offseason is what will become of David Ortiz. It would be a stretch to say that all signs are pointing towards him finally leaving town, but there are certainly some signs pointing towards that eventuality.

    Ortiz himself has changed his tune quite a bit over the last year or so. Sometimes he sounds like he's had just about enough of Boston. Other times he says he wants a multi-year deal. 

    But lately, Ortiz is saying he just wants to stay. 

    “Through the years, I always keep telling everyone how important it is for me to be part of this organization. This is what I know and this is something I want to be part of,” said Ortiz this week to Alex Speier of

    In the past, I've been in favor of the Red Sox parting ways with Ortiz this winter. It looked like the timing was going to be perfect.

    But this was before the Red Sox cleared $250 million in salaries, not to mention the left-handed bats of Crawford and Gonzalez. Finding a lefty hitter with power is going to be one of the club's biggest priorities this offseason.

    And frankly, they won't be able to do better than Ortiz.

    By the end of the year, Big Papi will have missed roughly a third of the season with his Achilles injury. What he's proven in 2012, however, is that he can still hit with the best of 'em. His 1.026 OPS would be leading the AL by a wide margin if he had enough at-bats to qualify.

    Ortiz is making roughly $14.5 million this season. It will take more than that, probably $15 or $16 million for one year, to lure him back to Boston in 2013. 

    Big Papi would no doubt prefer to get a multi-year contract offer, but his options are basically limited to the American League, and further restricted to teams with money.

    The Yankees have long been seen as a threat to steal Big Papi away from Boston, but it shouldn't be taken as a given that they will if Ortiz tests the free-agent waters. They need to keep their DH spot open in order to give their older players a chance to rest, and signing Ortiz to a multi-year deal worth $15 or $16 million per year doesn't really fit with their goal to get their payroll under $189 million.

    In all likelihood, Boston will still be the best fit for Ortiz this winter. Since the Sox have money to spare and a need for his bat in their lineup, they shouldn't let him go quite yet.

The 2013 Roster Could Look Like...

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    C: Jarrod Saltalamacchia/Mike Napoli

    1B: Mike Napoli

    2B: Dustin Pedroia

    3B: Will Middlebrooks

    SS: Mike Aviles/Jose Iglesias

    LF: Cody Ross

    CF: Jacoby Ellsbury

    RF: Ryan Kalish

    DH: David Ortiz



    1. Clay Buchholz

    2. Jon Lester

    3. Brandon McCarthy

    4. John Lackey

    5. Felix Doubront/Franklin Morales



    CL: Andrew Bailey

    RHP: Daniel Bard

    RHP: Alfredo Aceves

    RHP: Junichi Tazawa

    LHP: Andrew Miller

    LHP: Craig Breslow

    Long Man: Franklin Morales


    Prospects Waiting in the Wings

    Matt Barnes, RHP

    Allen Webster, RHP

    Xander Bogaerts, SS

    Jackie Bradley, OF

    Brandon Jacobs, OF

    Deven Marrero, SS

    Anthony Ranaudo, RHP


    If you want to talk baseball, hit me up on Twitter.

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