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We may be waiting a while for contract extensions

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Don’t expect them to be right around the corner

World Series - Boston Red Sox v Los Angeles Dodgers - Game Five Photo by Harry How/Getty Images

The upcoming offseason for the Red Sox figures to be a very different one compared to the previous winters in the Dave Dombrowski era. In each of the last three Hot Stove periods, Boston headed into the winter with at least one major need and a willingness to go all out to fill it. First, they traded for Craig Kimbrel and added David Price. The following year, they traded for Chris Sale (and also Tyler Thornburg, though that probably doesn’t belong in this conversation). Finally, last winter they went out and signed J.D. Martinez. Every year Dombrowski had his sights on a whale, and every year he brought him in.

That’s not the case this winter. The Red Sox just won 108 games and a World Series and they aren’t losing much of a significance. That’s not to say they’re not losing anything — Kimbrel is one of the top free agents on the market — but they don’t have major holes to plug this year. To put it simply, the roster is pretty much loaded, and while it’s always possible that Dombrowski will strike for a major move it’s far from a necessity at this point.

Now, this is not the same as saying nothing will be done this winter. The Red Sox roster is outstanding, but it’s certainly not perfect. They could use some relief help, whether it be Kimbrel or someone else towards the top of the market. I’d argue they could use two relievers this winter with one being relatively high-end, bu they need at least one. They could probably also use another starter, which I’ll get into later this week. Add in some depth options around the periphery of the roster and sorting out the catching situation, and Dombrowski has work to do this winter. It’s just not the whale hunting season it has been like the rest of his tenure.

World Series - Boston Red Sox v Los Angeles Dodgers - Game Five Photo by Sean M. Haffey/Getty Images

In fact, the biggest focus of the winter could very well be on the players who are already on the roster and aren’t in danger of going anywhere before Opening Day. Boston’s roster has a great young core that is largely in their prime, but these guys have been together long enough that they are set to hit free agency over the next couple of years. Next winter, Chris Sale, Xander Bogaerts, Rick Porcello and Brock Holt are all set to hit the open market. The year after that, Mookie Betts and Jackie Bradley Jr. end their time under team control. These are all important pieces — yeah, I put Holt in this conversation, sue me! — and the Red Sox are going to do everything they can to keep as many of these guys as possible.

So, we can expect extensions for many of these players to be the biggest storyline and theme of the winter. Every couple of weeks a reporter will have a new story on the status of extensions talks with various players, and there will be takes to be had about each report. Most of us will be waiting with bated breath for an extension to be announced, just like we were waiting all of last winter for the Martinez signing. This time around, however, we’re probably going to be waiting even longer.

The main reason for the impending wait is simply that getting these things done is pretty hard! Any contract negotiation is difficult, of course, but when there is no real timeline needed either or both sides can drag things out to get the best deal possible for themselves. Plus, all of the main extension candidates have reasons why things are difficult. Sale is coming off some injury concerns and has shown a tendency to fade late in the year. That doesn’t jive well with the money he’ll (justifiably) be commanding in negotiations. Bogaerts is coming off a career year and will want money to reflect that as his true talent. Betts is probably the second best player in the world and has shown he would like his pay to reflect that. That’s hard to do this far away from free agency. Bradley’s value is largely tied up in defense, which can be hard to quantify. None of these roadblocks are impossible to overcome, but these things take time.

MLB: New York Yankees at Boston Red Sox Bob DeChiara-USA TODAY Sports

In addition to all of that, it’s in the team’s best interest to wait until after the season begins to get these extensions going. This all comes down to payroll and the luxury tax. The Red Sox are going to pay the luxury tax again. Even without adding anyone else to their roster, they’ve already gone over the $206 million mark. Getting under it is out of the question. However, there is still the higher threshold of $246 million, which would cause them to drop ten picks in the draft if they exceed it. The Red Sox exceeded this mark last year, and they have said it’s not an obstacle this year if they feel it makes their team better. That should absolutely be the attitude, but I suspect they’ll do what they can to stay under. Which brings us to extensions. If any of these players signs an extension, it will change their current average annual value — it will increase it, specifically — if it is signed before the season begins. Average annual value, of course, is how luxury tax figures are determined.

The Red Sox have gamed extension timing to get around the luxury tax before, for what it’s worth. When Adrian Gonzalez signed his extension back in 2011, the team waited a few weeks into the year to officially announce it despite reports indicating it had been done for months. This allowed them to save $4.8 million in AAV, and kept them under the tax that year. The players have to be on board with this too — part of the luxury tax revenue goes towards the players, for what it’s worth — but I’d expect the Red Sox to push for this loophole in order to try and stay under the $246 million mark this year.

I take the team at its word that it will exceed that threshold to improve the team, and if they already go over then the extension theory won’t matter anymore. Furthermore, if a player (particularly Sale or Bogaerts) says they won’t sign an extension once the season begins, then this strategy should be thrown out the window. However, between the tax implications and the sheer difficulty of working out these kind of extensions, don’t expect any early announcements this winter.