Seven questions as the Red Sox take the plunge – or cautiously wade – into a pivotal offseason.
1. Why didn’t the Red Sox extend a Qualifying Offer to Lucas Giolito?
The list of potential reasons why the Sox opted not to extend a Qualifying Offer to right-hander Lucas Giolito range from magnanimous, to practical, to concerning.
Let’s go in reverse order. The most logical, and therefore worrisome, explanation is that the Red Sox did not want to offer a pitcher $22.05 million for one year after elbow soreness caused him to struggle in September and be left off their postseason roster.
Most practically, the Red Sox simply do not feel like he is worth $22.05 million for a year, but are open to a reunion in a more affordable, albeit multi-year format. (Giolito is expected to command a three-year deal in the $50-60 million range.)
The most generous version of events is that the Red Sox knew Giolito would have more suitors if he entered free agency without the strings of a QO attached to him. Do you think the Red Sox, who just spent the better part of a decade rebuilding their farm system and overhauling player development to finally create some legitimate depth, are so generous that they will turn down an opportunity to receive some draft pick compensation?
2. Do the Red Sox have more pitching depth than people realize?
Giolito may or may not return to the Red Sox, but several pitchers will be back next year. Among the players reinstated from the 60-day injured list last week were starters Kutter Crawford, Hunter Dobbins, Tanner Houck and Patrick Sandoval. Between them and Cooper Criswell, whom the Red Sox signed to a fully guaranteed one-year, $800K deal late last week, I think the pitching department has slightly more depth than people realize. Slightly.
(Exclude Houck for now; his late-summer Tommy John surgery effectively rules him out for most, if not all, of the 2026 season.)
Don’t take any of this to mean the Red Sox should not be trying to add a starter this winter. They entered this season with far more depth, and were still almost running on empty by September.
3. Why did Trevor Story opt in, and how does it impact the Red Sox?
It wasn’t entirely surprising when Story opted into the remaining two years of his six-year, $140 million contract. He feels loyal to the Red Sox, who stuck with him through injury after injury.
Yet with the current Collective Bargaining Agreement expiring next offseason and the expectation that all heck will break loose in the ensuing negotiations between the league and players, it was somewhat surprising to see a veteran player decide not to pursue the security of a longer-term deal now, after his best season in nearly half a decade.
Could the Red Sox move him to second base, though? I think so.
There were questions about Story’s arm holding up at the game’s most challenging defensive position when he returned to short after Xander Bogaerts became a free agent, and before Story’s elbow surgery in January ’23 and shoulder surgery in April ’24. Those same doubts poked holes in Story’s otherwise impressive comeback season this year; he made 19 errors – five more than his previous career-worst – including seven errors in his final 19 games. In late September, after his sixth error in a seven-game span, he said that while it was not an excuse, his body was tired after a long season.
4. How can the Red Sox strengthen their catcher setup?
Connor Wong and Carlos Narváez each underwent surgeries last month; a right hand carpal boss excision for the former and a left knee meniscectomy for the latter. Both are expected to be ready by spring training, but are they a strong enough pairing to get through another, hopefully better Red Sox season than this one?
Wong only played 63 regular-season games, a sharp decline from the 126 games he played in each of the previous two seasons. This was in part because the rookie Narváez stepped into the everyday role and cemented himself as the primary catcher, but largely because Wong’s offensive production practically vanished into thin air.
After a career-best offensive campaign in ’24 when he hit .280 with a .758 OPS, 24 doubles, and a career-highs in hits (125), home runs (13), and RBI (52), Wong batted .190 with a .500 OPS this year. His 32 hits included eight doubles that were his only extra-base knocks, and he drove in just seven runs. Combined with his defensive struggles – he ranked in the 6th MLB percentile in Blocks Above Average and 21st percentile in Caught-Stealing Above Average this season – the picture painted is not a pretty one.
5. What should we glean from the exodus of scouting and player development staff?
Is it a compliment, matter of concern, or a combination of both that so many key members of an improved Red Sox player development machine have left in the last two months?
First, assistant general manager Paul Toboni, who left to become the Washington Nationals’ president of baseball operations in September. He was Red Sox chief baseball officer Craig Breslow’s favorite for a promotion to the vacant GM role, and team president and CEO Sam Kennedy described Toboni’s departure as a “brutal loss” for the organization.
Red Sox director of amateur scouting Devin Pearson and field coordinator Andrew Wright joined Toboni in the nation’s capital, and Red Sox director of pitching Justin Willard agreed to become the New York Mets’ pitching coach.
It speaks highly of the Red Sox that teams want to follow in their footsteps by luring away their employees. It also could say something about the state of the Sox that so many key contributors are happy to leave.
6. How likely is a Red Sox-Alex Bregman reunion?
The Red Sox should do everything in their power to bring Alex Bregman back long-term, but my optimism that it will get done is fading by the day.
Which leads us to our seventh and final question…
7. Are the Red Sox finally ready to be ‘THE Red Sox’ again?
Yes, the Red Sox have made some enormous trades (Garrett Crochet), handed out some mega-extensions (Crochet, Roman Anthony), and got Bregman during spring training last year.
However, those are not the type of moves that defined the Red Sox teams that won it all four times in this century. I’m talking about bold, big-market, no-limit contracts that verge on outlandish. That’s what it takes to get a deal done nowadays.
Until the Red Sox show that they are willing to get truly uncomfortable with a long-term deal for a free agent position player, they are not all the way in on themselves. Bregman’s three-year, $140 million deal had two escape hatches, and it was presumed almost from the start that he would use one of them. And so he has!