Why Xander Bogaerts chose to sign with the Padres over the Red Sox

SAN DIEGO — As executives and agents scattered late Wednesday night at the conclusion of a Winter Meetings that featured delirious round-the-clock spending, a final shockwave swept through the Manchester Grand Hyatt that registered on seismographs in Boston: Xander Bogaerts had reached agreement with the Padres on a startling 11-year, $280 million contract.

Another Red Sox star is gone, the result of a months-long series of missteps by the only organization for which Bogaerts has ever played.

The team drastically misread the market for Bogaerts repeatedly, right up to the end. Entering the Winter Meetings, baseball officials were divided over what a Bogaerts contract might eventually look like, with some speculating he might secure a six-year deal in the $150 million range and others envisioning a seven-year deal that could sneak past $200 million.

Yet the spending frenzy that unfolded in San Diego — an 11-year, $300 million deal for Trea Turner and the Phillies in which the Padres had missed out with an even bigger offer; a nine-year, $360 million agreement between Aaron Judge and the Yankees in which the Padres had likewise emerged as a late bidder — suggested that $200 million represented a likely floor for where the Bogaerts market would go.

Even so, over the course of the week, Sox officials expressed surprise or skepticism that bidding for the 30-year-old Bogaerts would reach that mark. The team behaved accordingly.

According to a major league source, the Red Sox made a six-year offer with an average annual value of roughly $27 million — a higher AAV than the Padres ($25.5 million). Still, even with some belief in Bogaerts’s camp that the Sox would raise their offer, the gap in the number of guaranteed seasons was so enormous that the separation between the offers was decisive.

The Red Sox weren’t even in the picture at the end. Along with the Padres, three to four other teams saw Bogaerts being worth at least $200 million. So far behind were the Sox that Bogaerts told a friend he had “zero choice” but to eliminate what was long his team of choice and have agent Scott Boras negotiate with the others.

That last misstep might not have been necessary but for others that preceded it. The Sox made possible the dissolution of their relationship with a franchise cornerstone — the team’s last link to its 2013 title, and one of the final ones remaining to the 2018 championship — through a bafflingly low opening offer in the spring.

In 2019, one year from free agency, Bogaerts — then 26 — pushed Boras to get a deal done with the Red Sox. The result was a below-market, six-year, $120 million offer that proved a relative bargain, as Bogaerts spent 2019-22 as arguably the most productive offensive shortstop in baseball.

That deal included an opt-out after the 2022 season, giving Bogaerts the opportunity to walk away from the final three years and $60 million for a more lucrative contract. The Sox and Bogaerts spoke of their desire to extend the relationship of a player who signed his first professional contract with the team in 2009, and met to discuss a potential extension in spring training this year.

But the Sox offered Bogaerts just one additional year and $30 million to pass on the right to opt out, essentially, a commitment of four years and $90 million. Bogaerts was stunned. The Sox had just signed Trevor Story — a player whose performance had not matched that of Bogaerts — to a six-year, $140 million deal.

Bogaerts, a source suggested, would have been open to a new deal that was in the range of what Story received. The five-year, $151 million extension that Astros star Jose Altuve landed several years earlier likewise represented a framework that Bogaerts would have welcomed.

Bogaerts said farewell to Fenway on October 5.Jim Davis/Globe Staff

But the Sox’ offer was a non-starter. Bogaerts left spring training with a disappointed realization that the season might be his last with the Sox.

Bogaerts initially suggested he didn’t want to negotiate a new deal in-season but softened that stance in May. Boras likewise said he would be open to calls. But the Red Sox never attempted another contractual outreach during the season.

Toward the end of the year, several team officials told Bogaerts that the club wanted to retain him. But it was only after the season that front office members and members of the ownership group sat down with Bogaerts to revisit talks about a new deal, something that, according to a major league source, happened at Fenway Park.

By that point, free agency — which would commence after the World Series — had gotten so close that Bogaerts was all but certain to reject any deal that didn’t come close to what he and Boras anticipated to be his market value.

Meanwhile, though the Red Sox repeatedly proclaimed Bogaerts to be their top offseason priority, they never came close to making an offer that he and Boras perceived as near his market value.

Over a 10-month period, the Sox missed out on a series of chances to convince Bogaerts to bypass the open market.

The 30-year-old Bogaerts has been a part of the Red Sox' organization his entire professional career.John Tlumacki/Globe Staff

Once other teams had a chance to meet with Bogaerts, his value rose. Chief baseball officer Chaim Bloom and some of his lieutenants didn’t share that assessment. The Red Sox were then left in the dust.

It’s fair to suggest that the Padres gave Bogaerts a contract that was, to use a word employed by evaluators of several teams across the industry, “insane.” An 11-year commitment to a player through his age-40 season, no matter how talented, is likely going to entail a number of years with poor return.

But the Red Sox must now wonder whether the embarrassing departure of a star and face of the franchise could have been avoided with a more practical approach to deal-making much earlier in the process.

Compounding their missteps: The Red Sox got almost nothing in return for Bogaerts. Because the team exceeded the luxury-tax threshold in 2022, they will receive just a compensatory pick between the fourth and fifth rounds of the draft.

It also was puzzling that the Red Sox promised Bogaerts that he would not be traded but did not attempt to capitalize on that gesture by attempting to negotiate in-season.

Why not just trade Bogaerts if their valuation offered no path to an extension? The team’s trade of Jon Lester at the 2014 deadline, though painful, netted Yoenis Cespedes, who in turn allowed the team to acquire Rick Porcello in the offseason.

Even if a trade of Bogaerts was not deemed acceptable, the Red Sox erred when they did not shed players at the trade deadline — J.D. Martinez, for instance — who would have allowed them to duck under the luxury-tax threshold. The team was 52-52 and mired in last place at the time.

Bogaerts' future is now as a San Diego Padre.John Tlumacki/Globe Staff

Such a move would have given the Sox greater compensation (a pick between the second and third rounds) once Bogaerts left, while diminishing the penalties for signing other top free agents who received qualifying offers.

Ultimately, the Red Sox approached a franchise icon clumsily. The result? Bloom, who often speaks of the need to work in service of the present and future, weakened the roster, failed to make decisive moves to improve its prospect talent base, and left a distrustful fan base to confront the void of a departure of a beloved star.

“The Sox without the ‘X’ are just so-so,” Boras gleefully proclaimed Tuesday.

Now they have the difficult task of proving him wrong.

More on the Red Sox during the Winter Meetings

Alex Speier can be reached at alex.speier@globe.com. Follow him @alexspeier. Peter Abraham can be reached at peter.abraham@globe.com. Follow him @PeteAbe.