The Boston Red Sox entered this offseason with an impossibly long checklist. They needed a new manager, for starters, and then they had to go on a scavenger hunt for talent.

There’s not much remaining on Boston’s checklist, and that’s the good news. General manager Ben Cherington can probably count the number of hours of sleep he’s gotten since October on one hand, as he’s been too busy shoring up his club for the 2013 season.

The not-so-good news: Boston’s offseason hasn’t been perfect. I doubt there is such a thing as a perfect offseason, but the Red Sox’s winter certainly falls more in the “good enough” category than the “fantastic” category.

There have been disappointments along the way. So far, here are the five biggest ones that stand out.


5. No Extension for Dustin Pedroia…Yet

This is a minor gripe, as an extension for Dustin Pedroia was hardly a priority for the Red Sox this winter. An extension for him was more like a bonus item. A side quest, if you will.

Still, it sounded like a great idea at the time Joe McDonald of reported in November that the Red Sox were mulling a long-term extension for their star second baseman. If there’s one guy on the Red Sox who should stick around in Boston for years to come, it’s Pedroia.

Signing an extension now makes sense for Pedroia. He could wait for free agency to come, but that’s not likely to happen until after the 2015 season because he has two guaranteed years and an option year left on his contract. By then, he could be slipping into the twilight of his career.

Pedroia has further incentive to take what he can get now because of how he’s struggled with injuries in two of the past three seasons. If his body continues to betray him, the Red Sox will likely prove unwilling to give him an extension. 

The Red Sox have incentive to make something happen too. Pedroia‘s value is somewhat low after he endured a trying season in 2012, so they may be able to shave a couple million bucks off his fair market value. 

But more importantly, the Red Sox should want to get Pedroia locked up before New York Yankees second baseman Robinson Cano sets the market for star second basemen in free agency next winter. The Red Sox don’t want to have to try to hammer out an extension for Pedroia after Cano puts the going rate for star second baseman at, say, $20 million per year.

Pedroia told WEEI in December that he hadn’t heard anything new about a possible extension, so it’s apparent that neither his people nor the Red Sox are in a hurry to get something done.

Both sides should be willing to get the ball rolling sooner rather than later. The longer this thing drags out, the more complicated and harder to complete it’s going to become.


4. No New Superstar Players

After the 2011 season ended, the Red Sox lost a homegrown star when Jonathan Papelbon bolted for Philadelphia. In August 2012, they lost several more stars when Josh Beckett, Carl Crawford and Adrian Gonzalez were fired out of a cannon in the general direction of Los Angeles.

There never was any sort of promise that the Red Sox would replace their lost star power this winter, but they could have. They entered the offseason with a ton of money to spend, as well as a farm system that ranks among the very best in baseball. They had an excuse to make a big free-agent signing, a big trade or both.

But nope. The Red Sox have brought in some good, solid players this winter, but to call their new additions “stars” would be stretching the limit of that word’s definition more than a little bit.

Especially relative to the players the Red Sox have been linked to this winter. They were linked to slugging outfielder Josh Hamilton right up until he signed with the Los Angeles Angels, and there were plenty of rumors about them possibly going after Nick Swisher as well.

On the trade front, there were rumblings that the Red Sox would make a run at Arizona Diamondbacks right fielder Justin Upton, and they were also mentioned as one of many teams that have called the Miami Marlins about slugging phenom Giancarlo Stanton.

Yet no true stars have come to Boston. And with pitchers and catchers just around the corner, it’s highly unlikely that any new stars will be coming to Boston.

From a baseball standpoint, this isn’t a disaster. The Red Sox tried the All-Star team approach in 2011 and it failed miserably. They had their share of stars for most of 2012, too, and it didn’t make a difference. They’ve found out the hard way that assembling stars is no sure way to win games.

But from a rooting standpoint, Boston’s failure to land stars is a bummer. If acquiring stars during the offseason is good for anything, it’s getting a fanbase even more excited for the arrival of baseball season. Fans can come to love a star-studded team before they even see it in action.

Boston fans can be forgiven if they’re not in love with the 2013 Red Sox yet. These Red Sox may very well be a great team in the end, but their first order of business is to win over fans who are stuck in a rut of skepticism.


3. No Significant Upgrades for Starting Rotation

The superstar concern doesn’t really apply to Boston’s starting rotation. The only star they could have realistically added was Zack Greinke, and he was a) too expensive and b) a questionable fit.

But the Red Sox had to make some sort of significant upgrade to their starting rotation this winter, lest they risk enduring another season with a starters’ ERA over 5.00.

It didn’t have to be Greinke. Somebody like Anibal Sanchez would have done nicely as a free-agent signing, and Josh Johnson looked like a good get before the Marlins traded him to the Toronto Blue Jays. Somebody like Brandon McCarthy would have been a good high-upside gamble.

To date, the Red Sox have only made one notable addition to their starting rotation: veteran right-hander Ryan Dempster.

He, unfortunately, does not make the cut as a “significant upgrade.”

Dempster—who got a two-year, $26.5 million contract—should be a decent innings-eater at the back of Boston’s rotation, but likely no more than that. His 12 starts as a member of the Texas Rangers in his first foray into the AL didn’t go so well, as he posted a 5.09 ERA and a 1.44 WHIP.

The Red Sox could still go after Kyle Lohse or Shaun Marcum to round out their rotation, but they look totally prepared to head into the season with a rotation consisting of Dempster, Jon Lester, Clay Buchholz, Felix Doubront and John Lackey.

If so, the Red Sox are banking on Lester and Buchholz turning back the clock to 2010, Doubront making strides after an up-and-down rookie season and Lackey returning to form after missing 2012 recovering from Tommy John surgery.

The upside for this rotation is there, but so is the downside, which is more ominous than the upside is encouraging. If good fortune doesn’t find the Red Sox, they’re going to regret not adding a rock to their rotation during the winter.


2. So Much Money Has Bought Only So Many Wins

Grievances aside, there’s no doubt that the Red Sox are a far better team now than they were at the end of the 2012 season, when they barely resembled a major league ballclub.

The Red Sox have added players to areas of need who are easily better than the players they had in those areas before. They look like a major league ballclub again, which is nice.

But it’s cost an awful lot of money to make these additions, and looking like a major league ballclub and looking like an obvious contender are two different things. The Red Sox have spent like an obvious contender, but they don’t resemble one.

Curious about exactly how much money the Red Sox have committed to the 2013 season? Well, according to, they went into this offseason with about $45 million in salaries committed for the 2013 season. That number has since grown to over $125 million.

So $80 million is your answer. Give or take a few thousand bucks.

To put that in perspective, consider the Blue Jays. They had about $61 million in salaries committed for 2013 at the start of the offseason, and that number has grown to a little over $100 million.

The Blue Jays won only four more games than the Red Sox in 2012, yet they’ve arranged a significantly more talented team for 2013 than the one the Red Sox have arranged at half the cost. 

The best-case scenario for the Blue Jays involves at least 95 wins. The best-case scenario for the Red Sox involves something more like 90 wins, and that’s if everything goes well.

The smart money is on them finishing slightly below the 90-win plateau, however, which would take them out of the running for the AL East title and likely out of the running for a wild-card berth.

Going from 69 wins to 80-something wins in a single season would a big leap forward to be sure, but there must be a sizable portion of Red Sox Nation that’s tired of seeing busy offseasons followed by October-less seasons.


1. The Entire Mike Napoli Situation

The four disappointments I just rattled off are but a tiny speck in the rear-view mirror of this disappointment.

Myself and B/R Red Sox Featured Columnist Benjamin Klein are in agreement that the Mike Napoli situation is by far the biggest smudge on what has otherwise been a solid offseason. Boston’s agreement to sign him to a three-year, $39 million contract wasn’t universally beloved in the first place, and the situation itself became bad and has since become worse.

Napoli first agreed to sign with the Red Sox more than a month ago during the winter meetings. A couple of weeks ago, Ken Rosenthal of reported that Napoli‘s deal was being held up by a preexisting hip issue and that the Red Sox were trying to “rework” the contract.

On Friday, Jim Bowden of ESPN and SiriusXM shed some light on what exactly the Red Sox are trying to do:

This explains the delay, as it stands to reason that Napoli doesn’t want his three-year deal to turn into a one- or two-year deal. This also makes one skeptical about what’s going to happen with Boston’s vacancy at first base.

If Napoli is signed, the Red Sox won’t be able to convince anyone that they haven’t agreed to put damaged goods at first base. The jig is already up.

If Napoli isn’t signed, the Red Sox will be forced to find a replacement from a very weak crop of free-agent first basemen. The better course of action available to them would be to trade for Washington‘s Mike Morse, something they’re supposedly interested in doing.

But the Red Sox won’t be the only ones in on Morse if they decide to go that route, so for now they can’t risk pulling away from Napoli and then pursuing Morse. 

As such, the Red Sox really have no choice but to stay the course and to try to make the best of a bad situation, whether that means getting Napoli to agree to an altered deal or trading for Morse and then washing their hands of Napoli.

If the Red Sox trade for Morse or somebody else, a crisis will have been averted. If they wind up with Napoli in the end, they’ll have to require all fans to cross their fingers when inside Fenway Park.


Note: Stats courtesy of unless otherwise noted. Salary and payroll information courtesy of Cot’s Baseball Contracts.


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