Wednesday was the best day Boston Red Sox fans had seen in a while. The oft-infuriating front office run by Chaim Bloom — and installed with cost-cutting haste by team owner John Henry — finally agreed to sign a homegrown star to a long-term deal, finally sidestepped an emotionally draining quagmire instead of barreling into it. Effervescent third baseman Rafael Devers, a two-time All-Star at only 26 years old, will reportedly be staying at Fenway Park on an 11-year, $331 million deal that begins in 2024.

That inspired mostly relief among a fan base now on heightened alert for losing beloved stars. Since Henry ousted Dave Dombrowski and hired Bloom in October 2019, less than a year after a glorious victory in the 2018 World Series, the Red Sox traded away Mookie Betts and failed to negotiate an extension with Xander Bogaerts. They watched impotently as Bogaerts accepted a massive offer from the San Diego Padres in December, just the headliner of a bleak winter as J.D. Martinez and Nathan Eovaldi also walked. In signing Devers, Bloom and the ownership group probably staved off a fan revolt — or, worse, apathy.

Momentous as the Devers extension could be, it doesn’t reset the track record of this front office. Nor does it change the not-so-promising immediate outlook for the team in a stacked AL East. Paying up for a star player is a decision the Sox didn’t make when given numerous other opportunities in the past three years.

"It’s the average annual value the Red Sox never gave Betts. It’s the 11-year commitment they wouldn’t give Xander Bogaerts. It’s the top-of-the-market splash they wouldn’t make with Aaron Judge or Carlos Correa or Corey Seager,” The Athletic’s Chad Jennings wrote. “Devers is the player they’ve chosen to build their future around.”

Is Devers the right choice, though? Many would say the Red Sox had to sign him now. But evaluating Wednesday’s deal requires reevaluating the decisions that put their backs against the wall.

The Xander Bogaerts decision(s)

Maybe it was always going to be one or the other, Bogaerts or Devers. Given the concerted effort to accumulate infield talent in the minor-league system — most notably Marcelo Mayer, a 20-year-old shortstop who ranks among the 20 best prospects in baseball — the Red Sox might have viewed it that way.

The reported conversations with Bogaerts didn’t suggest the team was seriously attempting to keep him. The New York Post reported that Boston’s extension offer was four years and $90 million, essentially adding a year and $30 million to the three years and $60 million he opted out of following the season. They reportedly bumped that up to a total of $120 million in October, but Bogaerts nevertheless opted out. Their bid once Bogaerts hit the open market never even eclipsed the deal Dansby Swanson got from the Cubs. Bogaerts accepted 11 years and $280 million from the Padres.

There’s a solid case to be made against that type of deal for Bogaerts. He is 30 years old and won’t be able to stick at shortstop forever. If the team’s top prospects, including rookie first baseman Triston Casas, pan out, it would be tough to find a new defensive home for Bogaerts. But this is also a team that signed the up-and-down slugger Trevor Story to a six-year, $140 million deal prior to 2022 and then got a second straight worrisome down year.

Bogaerts vs. Story is a very different comparison than Bogaerts vs. Devers. And the latter wouldn’t even need to be had if the Red Sox sat out the sweepstakes for second-tier shortstop talent and prioritized their own top-class player. Or if they were the sort of team wired to acquire real difference-makers and figure out the exact fit later (a quandary that hasn’t slowed down the Padres). If the Red Sox took that approach, perhaps they would've sought the services of Carlos Correa or Corey Seager last offseason and had a much more comfortable fallback plan if negotiations with Bogaerts or Devers soared out of their preferred price range.

Whichever way you want to slice it, Bogaerts has been a difference-maker in a way Story is not. By FanGraphs’ WAR, he has been one of the 15 best position players in baseball — since his first full season in 2014, over the past five seasons and in 2022. He’s about as steady a star as you’ll find in MLB.

FanGraphs projects Story, already 30, for 2.9 WAR in a modest bounce-back year. He’ll make just about $2 million less per year than Bogaerts through 2027 and begins his decline years from a much lower pedestal.

Bogaerts and Devers, meanwhile, are pegged for almost comically identical total value (4.6 vs. 4.5 WAR) in 2023, though Devers' new contract doesn't kick in until 2024. Devers will pull ahead in coming years, as his 20s persist and his bat stays quick. He has never quite been the first-class player Bogaerts has been or the elite MVP that Betts was, but he has much of his prime left to add to his résumé.

The Mookie Betts decision

When Henry imported Bloom from the Tampa Bay Rays, his marching orders were widely known: Get the payroll under MLB’s competitive balance tax threshold.

Bloom’s method was immediately painful and has grown increasingly regrettable. He traded Mookie Betts to the Los Angeles Dodgers, with whom Betts signed a 12-year, $365 million extension that he has said he would've accepted from the Red Sox, had it been offered.

Boston’s return in the deal — limited by the single season of team control remaining for Betts and the inclusion of an expensive, aging David Price — consisted of outfielder Alex Verdugo, catcher prospect Connor Wong and middle infield prospect Jeter Downs. Verdugo has been an average regular at best. Wong is viewed as a backup option or potentially a utility player. Downs was designated for assignment earlier this winter. Betts, of course, has continued to be one of the game’s elite all-around superstars. The trade is already an embarrassment and might be remembered in the same breath as Boston’s sale of Babe Ruth, among baseball’s all-time boondoggles.

The stated purpose of that whole saga, of Bloom’s project in Boston, was to de-Dombrowski-fy the franchise, take it off a decade-long record roller-coaster and create a sustainable winner. One obvious step on the way there, for Henry and the ownership group, was getting under the competitive balance tax threshold at least once to reset their penalties, which escalate for teams that pay in consecutive seasons. Bloom did that, sliding under the soft cap in 2020 and 2021 (though the 2020 season was shortened by the pandemic).

The Red Sox have, however, very much remained on the roller-coaster, sandwiching a 2021 ALCS run between two seasons of doom and gloom. In the meantime, the rest of baseball seemed to learn a lesson about building winners from the Betts debacle.

What the rest of MLB learned from the Red Sox's mistakes

Since the Betts trade, a bevy of top talents have inked early career extensions, including the Seattle Mariners’ Julio Rodriguez, the Tampa Bay Rays’ Wander Franco and the San Diego Padres’ Fernando Tatis Jr. As Tatis proves, there are some risks involved in those moves, too, but teams are overwhelmingly choosing them over the paths the Red Sox took with Betts, Bogaerts and Devers. Even the Nationals’ stunning decision to trade Juan Soto with multiple years of team control left spoke to a desire to avoid a Betts situation: They reaped far more prospect talent by moving him early and declining to attach bad contracts in the deal.

The Atlanta Braves offer an example of a path the Red Sox might have taken if they intended to build a consistent winner. They got to the extension trend early by signing Ronald Acuña Jr. and Ozzie Albies in 2019 and have proceeded to make that practice their entire personality under Alex Anthopoulos. Virtually every Braves hitter you’ve heard of is under contract for a long time at an annual salary of $21 million or less. The players they couldn’t sign on their terms — Freddie Freeman and Dansby Swanson — were allowed to walk, with the club unburdened by desperation thanks to the solid core already in place and the maneuverability ensured by the reasonable annual commitments.

When Bloom took over the Red Sox, Devers was still a season away from hitting arbitration. That’s roughly the same moment the Braves signed third baseman Austin Riley, a notably similar player who’s about five months younger, to a 10-year, $212 million deal.

Since the start of 2021, here’s how they compare:

Devers: .287/.355/.530, 65 homers, 9.1 WAR

Riley: .288/.358/.529, 71 homers, 10.2 WAR

The WAR difference mostly stems from Riley's playing 22 more games and managing slightly better defense. Statcast rates Riley’s fielding as sixth-worst among regular third basemen over those two seasons. Devers ranks dead last.

That’s not exactly a knock against them — it’s a known fact that stellar bats carry their games and that they might eventually require a move to first base — but it’s something that has to be considered in the long term. It also seals their twin profiles.

The Braves are paying $8.89 million less per season, in the eyes of MLB’s tax calculation, for Riley than the Red Sox will pay for Devers. That difference arises because Devers had leverage; he’s only one year away from free agency despite his youth, and the Red Sox have suffered from letting other star-level talents go. If they had managed to negotiate a deal with Devers prior to 2020, it might've cost a bit more than Riley because Devers was younger at the time. Still, it would've given the team far more flexibility than the 11-year, $331 million pact they hammered out this week — flexibility they will likely need to actually compete. As of now, their projected 2023 depth chart ranks fourth in the AL East, per FanGraphs, with the young Orioles nipping at their heels.

Add the fact that the Red Sox are paying Story ($23.3 million) more than the Braves are paying for any player on their roster, and you can identify perhaps $30 million of wiggle room the Red Sox sacrificed from 2023 onward as a result of pursuing short-term tax savings for John Henry — along with, you know, the chance to watch Mookie Betts and/or Xander Bogaerts forever.

So yes, the Red Sox had no choice but to keep Rafael Devers’ smiling face and smashing bat. But it didn’t have to feel this desperate, and it didn’t have to come with so much punishment. That all stemmed from decisions the Red Sox very much chose to make.