Red Sox

With Red Sox wallets closed, your guide to wincing through the MLB Winter Meetings

This isn't the first time Boston's not been a big free-agent player, but it's certainly a rarity.

Mookie Betts, Red Sox
Will this celebratory shower of Mookie Betts on Sept. 29 be one of his last in a Red Sox uniform? AP Photo


All around the baseball-loving world this morning, there seems to be a hope from which we are excluded. The Hot Stove has been restoked without the Red Sox in their annual place as in on most everyone.

Gerrit Cole’s got a $245 million baseline offer from the Yankees. Stephen Strasburg might double the $100 million he opted out of after the World Series. His presumed former Washington teammate, Anthony Rendon, might net some of those Texas megabucks we first met 19 Winter Meetings ago, when Alex Rodriguez redefined what we think of when we think of a massive baseball contract.

That they all might come off the board by the end of the year, if not before Wednesday’s end of the annual Winter Meetings in San Diego, feels foreign and refreshing. A year ago, baseball needed four months to rustle up five free-agent contracts of at least four years. We could have six this offseason before you’ve even got your annual picture of your child bawling with a mall Santa.


Alas, we are not refreshing our Twitter feeds with hope this year. We’re doing it with fear. Because 15 weeks after $208 million became the number every Red Sox fan knows by heart, the 2020 team is both lacking and no closer to it.

And 10 years after “bridge year” was the refrain of the winter, the possible loss of Mookie Betts, and almost certain loss of some favorites, makes that bridge idea seem quaint.

I was reminded over the weekend, reading about old friend Theo Epstein’s Cubs’ need to clear payroll before engaging even with the free-agent bargain basement, when we previously wandered this lonesome winter road. It was 10 years ago this week, speaking at the 2009 Winter Meetings in Indianapolis, that the then-Red Sox architect couldn’t stop talking up mediocrity as battle plan.


“We’re kind of in a bridge period,” Epstein told reporters. “We still think that if we push some of the right buttons, we can be competitive at the very highest levels for the next two years. But we don’t want to compromise too much of the future for that competitiveness during the bridge period. We all don’t want to sacrifice our competitiveness during the bridge just for the future.”

Those Red Sox didn’t sacrifice, but they also didn’t win in 2010. Ten years after they dealt the previous year’s top draft pick at the Winter Meetings for young slugger Carl Everett, and 20 years after they blew away the free-agent market for top 1980s save man Jeff Reardon, Boston’s big Winter Meetings addition was Boof Bonser. Quite the downgrade in the headline and excitement departments.


And yet, a year later, the Red Sox were back to their default, showering $300 million on Adrian Gonzalez and Carl Crawford. And, four years later, they were also world champions again, the 2013 title thanks in large part to Jacoby Ellsbury and Clay Buchholz, two guys they’d refused to part with at those 2009 Winter Meetings in a deal for Curtis Granderson. (Granderson ended up in the Bronx via a massive three-team trade.) As a one-year thing, that bridge was sound.

Of course, the Red Sox didn’t really need to show restraint that winter, much like the Red Sox or the Cubs or the world champion Nationals — who said last week they can’t afford to keep both Strasburg and Rendon — don’t really now. In an excellent piece over the weekend, the Globe‘s Alex Speier laid out how the luxury tax came to be, how we got to our current state of it looming over everything, and the prudent reasons why Boston would be wise to reset its tax penalties this winter.


“The current [collective bargaining agreement] … introduced additional layers of penalties for spending $20 million and $40 million above the threshold. It also produced potential draft pick and international amateur spending penalties,” Speier wrote. “Finally, and perhaps most underappreciated, the new CBA created the possibility that major revenue-sharing payers such as the Red Sox, Yankees, and Dodgers could forfeit tens of millions of dollars in revenue-sharing rebates if they fail to get under the luxury tax threshold at least every third year.”

Prudent, however, does not equal necessary, not when the Red Sox, Cubs, and Nationals are all multi-billion dollar franchises. Scott Boras knows Washington’s “can’t” is really a “won’t,” and you should feel the same about John Henry’s in Boston. Trading a face of the franchise, be it Betts or Xander Bogaerts — who, at least in my eyes, offers far more value to another team and who could better help shuffle a bad contract out of town — is a choice, and one that shouldn’t be rationalized by keeping a draft pick with little chance of producing a player near as good.


Be that as it may, the Red Sox are where they are, and this won’t be a Winter Meetings like the ones we happily remember. Acquiring Chris Sale three years ago. Dan Duquette, operating under an apparent mandate from Yawkey steward John Harrington to goose the potential sale value of the franchise with a big signing, ripping Manny Ramirez away from Cleveland hours after Rodriguez signed with Texas in 2000. (Duquette and Ramirez both go into the Red Sox Hall of Fame next year, should you have forgotten how it all worked out.)

Heck, even Jerry Remy’s Red Sox story begins with a Winter Meetings. The Sox acquired the Somerset kid in a trade with the Angels at the 1977 get-together in Honolulu, the Globe‘s Larry Whiteside calling Boston shipping out promising pitcher Don Aase “another example of how the new Hot Stove League” of finally-Hall-of-Famer Marvin Miller “works, and how teams must gamble, sometimes, to try to keep pace in the race for the pot of gold at the end of the World Series rainbow.”


The Red Sox aren’t champions in 2018 without Sale, who came at the price of stud prospects Yoan Moncada and Michael Kopech, and David Price, who was the $217-million makeup call after losing Jon Lester. Is that worth their current place as talented albatrosses, whose places on the roster could lead Boston to shed Betts, arguably their greatest homegrown star of the draft era?

Your answer may vary. Whatever it is, it’s incumbent on Chaim Bloom to use this week to start answering the questions surrounding his 2020 Red Sox, who have no starting second baseman, no fifth starter, and apparently no more of Henry’s money to spend.


“We have to figure out how we go forward,” Bloom said on NESN’s new ‘After Hours’ show last week. “I think where we are as an organization, we wouldn’t be doing our job if we didn’t explore all of our options. But we do that recognizing we have a very good team and one of the best players in the game and we’re going to handle the situation accordingly.”

There are gambles in standing, and there are gambles in acting. It’s time for him to start gambling, even if it means it’s time for us to start wincing with every push of the ‘refresh’ button.

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