9 innings with the Red Sox, starting with an offseason to-do list
Chaim Bloom needs to bring in a true workhorse pitcher, and other thoughts.
Playing nine innings while congratulating Kevin Millar on shattering the all-time words-spoken-per-minute record by a NESN Red Sox analyst …
1. It’s not much fun, and there’s not much to be gained, to think about what the 64-68, last-place Red Sox are right now. So let me ask you: What’s your within-reason ideal for what happens this offseason?
To me, it looks something like this, at least in regard to the current roster: Sign Rafael Devers to a slightly more lucrative extension than the 10-year, $210 million deal Austin Riley accepted from the Braves a month ago. (As I said, this is a reasonable ideal, not necessarily an expectation. I suspect Devers wants and will command more than that.) Sign Xander Bogaerts — the heart of this thing — to a two-year, $65 million extension on the back end of the three years and $60 million he has remaining. Make Trevor Story a second baseman permanently.
And that’s just for starters.
2. What else? Bring back Nate Eovaldi on a short, incentive-laden deal. Offer Michael Wacha two years and $15 million. Re-sign Kiké Hernández to a two-year deal similar to the one he has now, which averages $7 million per season. Tell Garrett Whitlock he’s a relief ace until further notice, because the bullpen needs all the help it can get.

It’s kind of weird to say, but the Red Sox have so many roster holes that their best bet to fill them is counting on competent players who are already here to be better and healthier next year.
3. Of course, the Red Sox do need significant outside help, and they should have the money to be players in the free agent market. I’ve long wondered whether Chaim Bloom’s plan — and why their actions suggest they’re lukewarm on retaining Bogaerts — is to pursue a free agent shortstop such as Trea Turner or the ascending Dansby Swanson.
I know the working theory is that Story will move back to short if Bogaerts opts out, but he does not look like he has the arm for it anymore, and he’s a sensational second baseman. Keep him there.
4. I hope Bloom’s long-term plan isn’t to annually sign an abundance of pitchers to cheap deals and hope a couple of them outperform their contracts, as Wacha has this year.
The Red Sox need to find a genuine front-of-the-rotation workhorse. The best pitcher available in the upcoming free agent class is the Giants’ Carlos Rodón, who has been spectacular the past two seasons (including 2021 with the White Sox) but has the kind of injury history that has made Dr. James Andrews a rich man.
The Red Sox’ best bet for acquiring a front-line starter might be to trade from their improved prospect depth.
5. It’s tempting for multiple reasons to ponder a pursuit of Aaron Judge, who might be having the greatest free agent walk year in baseball history. But as much fun as it would be to steal the preeminent righthanded power hitter in baseball away from the Yankees, I can’t see the Red Sox allocating the resources required to sign an outfielder who will be 31 next April. I can’t see the Yankees allowing it to happen, either.

6. Every time Judge goes deep — he has 51 home runs — I’m reminded of the old Mo Vaughn line when he was a free-agent-to-be having an excellent year for the ‘98 Red Sox: “The price keeps going up.”
While Judge isn’t going to get close to Barry Bonds’s season record of 73 — feel free to apply your own asterisk here — I find myself rooting for him to break the Yankees record and the old MLB mark of 61 set by Roger Maris in 1961.
7. I can’t say I’ve liked Bloom’s approach to team-building, which for one thing seems to disregard the human element and the value of leadership. But any notion that he should be fired is ridiculous.
The Red Sox were two wins from the World Series last season. Was there some luck involved? Sure, as there is with every team that succeeds. This year is an outright debacle. So to me, his ledger is one win and one loss, with next season as the rubber match. He must get things right this offseason.
8. My respect for Bogaerts has grown this season, and I didn’t even know that was possible. He has long been a player worth admiring on the field and off, someone who always tries to do the right thing and has a history for coming through at a high level.
He has handled this frustrating season with candor and grace. And though his power is down and questions about how he will age are fair, he still has been productive and dependable. This is a player you keep, even if you suspect he’s slipping slightly.
9. He has been everything as a hitter that the Red Sox could have wanted when he was signed to a five-year, $110 million contract in February 2018. But J.D. Martinez is one player who should not be back.

He’ll turn 36 next August, and the bat speed just isn’t there anymore. He has 11 homers, a .768 OPS, and 113 OPS+ this season, which basically aligns him with Tom Brunansky’s 1990 season with Boston (15 homers, .780 OPS, 114 OPS+).
It’s highly unlikely that Martinez clinches a playoff berth with a spectacular catch, however.
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