Can the Red Sox really turn around this last-place finish? Big questions loom over the post-Mookie Betts era

Coming into the 2022 season, everyone knew two things to be true: The AL East was going to be tough sledding, and MLB’s expanded playoff format was likely to allow multiple strong teams from the division to compete. Four teams from the powerhouse division playing meaningful September baseball seemed imminently reasonable. It’s just that no one thought the one team left out of that group would be the Boston Red Sox.

Maybe we should expect it by now. The last 11 seasons have been a difficult-to-believe roller coaster in Boston. There have been five postseason appearances, including two World Series titles, and now there will be five last-place finishes alongside. There have also been three top baseball executives and four different managers.

Current chief baseball officer Chaim Bloom took over when owner John Henry fired Dave Dombrowski near the end of the 2019 season. The error that cost Dombrowski his job was paying the luxury tax for a team that finished third. This year, the Red Sox will pay the luxury tax again — for a space in the cellar. Now, Henry can afford it, it’s only a $900,000 bill, but his emphasis on getting under the tax at the time raise questions about how he will respond when his team needs reinforcements, not belt tightening. He walked back some of those comments but still acknowledged an incentive to be under the tax threshold — which carries escalating penalties for repeat spenders — to the Boston Globe, “I think every team probably wants to reset at least once every three years.”

Henry also didn’t really need to say anything for the priority to be apparent. After all, Bloom’s first major act at the helm was to trade away Mookie Betts.

If they’re going to defy the gravity of losing once again, there are major questions to be answered. And they start with the money.

Boston Red Sox's Rafael Devers, left, and Xander Bogaerts walk to the dug out during the fourth inning of a baseball game against the New York Yankees, Friday, Aug. 12, 2022, in Boston. (AP Photo/Michael Dwyer)

Will the Red Sox keep Xander Bogaerts and/or Rafael Devers?

The two best players on the Red Sox reside on the left side of the infield. Xander Bogaerts, the shortstop who is turning 30 on Saturday, will likely opt out of his contract after the season. Rafael Devers, the baby-faced 25-year-old third baseman, is under team control through 2023.

Whatever comes next for this team starts with these negotiations. Team president Sam Kennedy dismissed the narrative that the Red Sox aren’t willing to spend this week, so perhaps that portends an effort to get these deals settled.

Bogaerts, who makes $20 million per year under his current deal, will certainly be able to beat that on the open market. Take whatever scope you want — three seasons, five seasons — and he compares favorably to Carlos Correa, Corey Seager and Marcus Semien, all of whom signed for at least $25 million per year last offseason.

Devers, who could reach free agency right around his 27th birthday, presents Bloom and company with a less elite, but still crucial, version of the Betts situation. With one year left under team control, Devers has proven himself to be one of the 15 to 20 best pure hitters in baseball. His defense was subpar in previous seasons, but the numbers point toward improvement in 2022. Whether teams believe that will stick for at least a few years will have some sway over his earning power. Even if he is viewed as a future first baseman, the deal to secure him will likely need to come in north of the $21 million per year the Braves gave to Austin Riley and Matt Olson.

Can the Red Sox count on Chris Sale … or any other pitchers?

The 2023 Red Sox starting rotation looks … murky to say the least. Chris Sale’s return from Tommy John surgery was delayed by a rib cage injury. Then, he suffered a fractured finger on his pitching hand in his second start back in the majors. While recovering from that, he broke his other wrist in a bike crash and required season-ending surgery. Should he be good to go for 2023? Sure.

Nathan Eovaldi is set to become a free agent, along with Michael Wacha and Rich Hill. James Paxton — who signed a one-year, $10 million deal with several options — never pitched in 2022. The Red Sox presumably won’t pick up his $13 million team option, but he could exercise a $4 million player option.

Internally, 23-year-old Brayan Bello looks like a keeper after 12 games in the bigs (10 of them starts), but high walk totals lend at least some doubt about how reliable he will be in his first full season. Nick Pivetta can provide innings, but his best major league season involved an ERA merely 1% better than league average.

Mookie Betts is in L.A. How will Boston use the financial flexibility?

External options also exist, of course.

The turnover on the pitching staff could even be a good thing if Bloom has better luck on the market. That’s just far from a guarantee. Last winter’s attempts at efficiency included trading away solid outfielder Hunter Renfroe as his arbitration salary doubled. He continued with a nearly identical 2-WAR season, while the Red Sox flailed at finding even a serviceable hitter to replace him. Real upgrades usually cost real money.

It’s hard not to think about Betts’ eventual deal with the Dodgers, which he has said he would have signed if it were offered by the Red Sox. It’s a long deal, 12 years, but it carries an average annual value that now looks very reasonable for a perennial MVP candidate at $30.4 million. For at least the next two seasons they’ll be paying upward of $47 million for a mid-30s pitcher (Sale) and a shortstop with two straight worrisome seasons of mediocrity under his belt (Trevor Story).

So the question is: Will the misadventures in cost-cutting change their ways? The free agent class this winter is loaded. There are real impact players available — from Aaron Judge to Jacob deGrom to Trea Turner, if Bogaerts moves on or someone is willing to move positions. There are also potentially impactful, if riskier, options like Carlos Rodon who figure to be available in that Story range.

Bloom has also legitimately improved the standing of Boston’s minor league system. There is a good deal of talent in the pipeline, much of it in the coveted middle infield category. First baseman Triston Casas has already hit the ground running and figures to provide pop for the foreseeable future. Within two years, more high-level players should emerge as big-league help at the usual rookie bargain rates.

This isn’t a team or a city that usually waits a few years, though. It’s the Red Sox. They can afford the talent to rebound quickly, even in a daunting division. And until they secure it and achieve that rebound they’re going to be answering questions about the ill-fated cost-slashing assignment that ownership gave Bloom and the current regime in 2019.