Red Sox flubbed Xander Bogaerts talks even if they were smart not to match Padres | Chris Cotillo

SAN DIEGO — No matter how much as they wanted to keep Xander Bogaerts for the rest of his career, the Red Sox should not have matched the ridiculous, monstrous 11-year, $280 million offer that Xander Bogaerts accepted from the Padres late Wednesday night.

That doesn’t mean they didn’t bungle the Bogaerts saga from the start.

The Red Sox didn’t lose Bogaerts when they lowballed him with a four-year, $90 million offer in spring training — that was really a one-year, $30 million add-on to his existing deal — but they unquestionably moved the goalposts in negotiations. By insulting the face of their franchise in March, the Red Sox opened the door for him to leave in December. That possibility became a reality at the same time team executives boarded planes Wednesday night after the conclusion of the Winter Meetings to leave the exact city Bogaerts will call home for more than a decade.

Looking for his first payday, the 2019 version of Bogaerts wanted nothing other than to sign a long-term deal with the Red Sox and obtain some financial security in the process. The negotiations seemed relatively painless and a deal was struck as a significant hometown discount was reached. Three years later, with Bogaerts’ opt-out looming, things seemed to change. He still loved the Red Sox and wanted to remain in Boston but was also ready to cash in on a career that, through nearly a decade, had been close to flawless. Bogaerts never was driven by the allure of a payday as much as his old teammate Mookie Betts, but as the opt-out date loomed, so did Bogaerts’ understanding of his worth. If the Red Sox wanted him to stay, they’d have to pay.

For some reason, the Red Sox didn’t seem to take that seriously. Maybe they thought the laid back, always chill Bogaerts would happily take another discount, or maybe even take a lesser salary to help the front office build the next great Red Sox team around him. Maybe they figured he’d be so anxious to follow in the footsteps of his idol, Derek Jeter, and play for the same organization for his entire career, that money would not be a top priority. In any event, Boston lowballed him and came nowhere close to an agreement during spring training. For the first time, the idea of the shortstop’s potential departure became real.

Bogaerts never disrespected the Red Sox, but it became clear during spring training that his tone was changing. The ultimate team player drew a line in the sand and said he would not be willing to move off shortstop, even if the Red Sox brought in someone like Trevor Story or Carlos Correa. He jokingly questioned if the Red Sox still knew he was on the team. He reacted to Correa’s deal with the Twins in a way that suggested he was thinking about his own contract. On the eve of Opening Day at Yankee Stadium, he seemed very disappointed, if not hurt, that talks had not resulted in a deal.

Throughout another strong season, Bogaerts admitted that his pending free agency was weighing on him. He repeatedly called it the hardest season of his career and admitted something players rarely do, that he would try to soak in what could be his final weeks in a Red Sox uniform. True to form, Bogaerts’ big heart remained on his sleeve the whole time.

Once Bogaerts was able to opt out of his deal, he did, in a no-brainer move. Then came the wooing. A player who had been with the same organization since he was signed as a 16-year-old in 2009 got a chance to see just how green the grass was elsewhere as teams across the country courted him. Teams begged him to come. It was surely a stark contrast from how Boston’s spring offer seemed to beg him to leave.

Somehow, the Red Sox, who employ many top executives who have been with the organization for years, didn’t learn anything from the Jon Lester saga of 2014. The specifics are somewhat different but the similarities are striking. Lester, like Bogaerts, had grown up in front of the organization’s eyes and seemed like a good candidate to spend the rest of his career in a Red Sox uniform. In both situations, an insulting spring offer led to an unforeseen breakdown in negotiations. Both players ended up with upstart National League clubs whose championship windows were opening.

The Red Sox wanted Bogaerts back badly and believe they put in a good effort to do so. The six-year, $160 million offer reported by Alex Speier of the Boston Globe late Wednesday was actually a fair one even if it pales in comparison to The Godfather $280 million offer from San Diego. A $27 million average annual value for a player’s age 30-36 years is perfectly reasonable. One Red Sox source said he believed the offer was “a really good one.”

It ultimately didn’t matter. The Padres, after losing out on both Trea Turner and Aaron Judge despite offering more than the deals they took, were uber-motivated to add a bona fide star to an exciting core. By letting Bogaerts get to this point, the Red Sox opened the door for another team to get stupid and make Bogaerts an offer he could in no way, shape or form refuse. Put simply, the Red Sox flubbed around in March. Nine months later, they found out.

No one with the Red Sox, publicly or privately, will wave a clenched fist at Bogaerts for taking the mega-deal he did. It’s smart business. It was a no-brainer. And it’s not a level the Red Sox should have even thought about touching.

But there’s no excuse for letting it get to this point in the way it transpired. And because of that, another homegrown star is walking out the door.

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