Since the Red Sox were eliminated from the postseason, most talk regarding the team has steered towards one of two things: the former Sox in the World Series, and what the team might do during this upcoming offseason. We’ve seen more than enough about the former, from Terry Francona to Jon Lester, so it’s about time we start discussing the latter.

The Red Sox only have a few holes in the roster as it’s currently constructed, but they’re obvious. The retirement of David Ortiz makes the roster more flexible, but it also takes away one of the best offensive players of 2016. The impending departures of Koji Uehara, Brad Ziegler and Junichi Tazawa also leave a lot of spots open in the bullpen. Mookie Betts and Xander Bogaerts essentially require contract extensions at this point. Clay Buchholz’s option will probably be picked up, but his usage is still up in the air. As you can see, there’s quite a bit on the Sox’s itinerary.

Naturally, there are already suggestions as to how best to fill the holes. Signing Edwin Encarnacion or Jose Bautista is a big one. Adding Kenley Jansen seems to have picked up steam in recent weeks. Trading for a first baseman like Joey Votto or Paul Goldschmidt has been out there for a while. Then there’s the more conservative options, like bringing back Uehara and Ziegler. Most of these options are viable, sure. But most of them are also costly. A signing of Encarnacion, Bautista, or Jansen would likely require a big contract relative to their peers, and a trade for Votto or Goldschmidt is going to require giving away at least a few good prospects. The Red Sox can’t clean out all their resources now, not with what’s coming the next two winters.

Next winter, Jake Arrieta, Yu Darvish and Craig Kimbrel could all become free agents. All of them will require a burdensome contract to reel in. All of them would make a great fit on the Red Sox. The year after that is even more bonkers. Guys like Bryce Harper, Josh Donaldson, and Madison Bumgarner all hit free agency, making it a winter that could define the next decade. On top of all that, that’s when David Price can exercise the opt-out in his contract. The Red Sox would behoove themselves to take advantage of that potential upheaval, and the preparation can begin now with little short-term harm to the team.

The first order of business would be to try and lock up the two players vital to the Red Sox’s core in Betts and Bogaerts. This is also where you begin to outline exactly how much you could have to spend over the next two winters. The Red Sox have to move now on this because if they get better – and all signs point to them doing so – it’ll become even harder to retain them, and these are two budding stars they can’t afford to lose. With Jackie Bradley Jr., however, they can wait and see. He’s a superb defensive outfielder, but the offense comes and goes with him, evidenced by the .926 OPS in the first half of the season, and the free fall to a .728 mark in the second half. He’s not as urgent as the other two. After that, the next thing should be to work on the relief pitching. Bringing back Uehara is a nice idea, but he showed clear signs of regression in 2016, and would have to come back on a much lighter contract than what he had. Brad Ziegler is a candidate for re-signing, but there have been rumors that the Diamondbacks would like to get him back this winter. Kenley Jansen is a nice idea, and would be one hell of a bullpen combo with Kimbrel. As relievers go, he’s one of the best and most consistent out there. He’ll probably ask for a contract like the four-year, $50 million one that Jonathan Papelbon got back in 2011, and while that’s not the most punishing thing, it’s steep for a guy who might only pitch four percent of all possible innings pitched. Of the possible big contracts, his is probably the safest. Hitting should be the last thing on the Red Sox’s list. The hole left by Ortiz isn’t as huge as you might think. You don’t need an Encarnacion or a Votto to make up for some of that offense. The Red Sox rolled out the best offense in the American League with a .269 TAv, and it won’t hurt to drop a little, especially with the competition in the AL East losing a lot of their key players, most notably Toronto. Instead of vying for Encarnacion or Bautista, the Red Sox would probably come out better by going for someone like Matt Holliday or Carlos Beltran for a year or two. It makes the roster a little inflexible, but the Red Sox don’t have a comparable hitter on the roster, and no, Travis Shaw isn’t going to cut it. A short contract with an older hitter would do wonders for the team.

A plan like that would keep the Red Sox in the running for whatever they want over the next two summers. They don’t need to throw money everywhere. The pitching needs some tune ups in the relief corps and the offense doesn’t require a drastic overhaul. The Sox could probably spend $65M on just Jansen and Holliday, call it a winter, and still come to Spring Training as a pretty strong favorite to win another AL East pennant. They’d be limiting themselves in the near future by spending a lot in the upcoming one.

This will be the second winter with Dave Dombrowski at the helm, and I’m very curious to see what he’ll do. The Red Sox are definitely changing, and adeptly navigating the next few years could prove to be both career- and franchise-defining. The thing about success is that it’s a lot easier to initially achieve it than to consistently do so. Being conservative this offseason could go a long way to keeping the Red Sox winning for a long while.

Photo by Gary A. Vazquez/USA Today Sports Images