Three years later, the Red Sox...

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.

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.

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.

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.

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.

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.