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One of my first early memories of heartbreak as a Red Sox fan was the Jon Lester saga of the 2014 offseason. I absolutely loved Jon Lester. He was everything you could possibly want in a big-game pitcher, a true “give me the ball and get out of my way” kind of guy. There was not a doubt in my mind he was going to come back. He loved Boston, Boston loved him. Why wouldn’t he want to be here? But Lester didn’t come back. Instead, he signed with the Chicago Cubs, and helped them win a World Series he should have won in Boston.


As heartbreaking as that failure was, it taught me a valuable lesson: Don’t get emotionally attached to players. Baseball is a cruel, heartless business, and nobody is a guarantee to stick around forever. That’s why I wasn’t heartbroken when Mookie Betts got traded to the Dodgers prior to the 2020 season. Yes, Mookie was a generational talent and one of my favorites, but the Red Sox were in payroll hell, and a Mookie contract would handcuff for years to come. The true root of the problem was that they were paying Pedroia, Price, Hanley Ramirez and Sale huge sums of cash for little to no production, and that forced their hand. It was unfortunate to lose a player of that caliber, but at least they were able to get value back and rid themselves of the Price contract.


Nearly two years later, I, along with all other Red Sox fans, are being tested again with the loss of Xander Bogaerts. Bogaerts was, if possible, even more popular than Mookie. He was the one player connecting the 2013 teams and the 2018 teams, an accountable and vocal leader in a clubhouse looking for a replacement for the larger-than-life David Ortiz. Bogaerts was the consummate professional. He played every day, he played hard every day, and he always held himself and his teammates accountable.


From an emotional standpoint, this sucks. It also sucks how much we got duped by the front office and ownership. Two months of hearing about how Bogaerts is their “top priority” and “Plan A” and in the end, they don’t even get close to signing him. That’s inexcusable. That’s embarrassing. Not to mention that if they just offered that 6 year/$160 million deal in the spring, they probably got the deal done.


There are, however, two sides to this story. Let’s now take emotion out of the equation, and look at this deal from a purely analytical standpoint. There is not a doubt in my mind that this contract is going to age extremely poorly for the Padres. 2022 was one of the worst offensive seasons of Bogaerts career, a point reinforced by both the surface-level and advanced metrics. His .833 OPS was his lowest since the 2017 season, and while his .307 batting average was near the league leaders, it was helped by extreme batted ball luck, .362 batting average on balls in play (BABIP), as the league average is just around .300. He was also below league-average in average exit velocity, hard hit percentage and barrel percentage.


What Bogaerts made unquestionable improvements in last year was his defense. After totaling negative outs above average (OAA) in all but one of his seasons since 2015, he totaled a +5 mark in 2022, a reflection of offseason commitment and better positioning. Yet with the new rules against shifting and declining footspeed (2022 saw a career low in sprint speed), it stands to question if he can sustain those improvements.


None of this is meant to bash Bogaerts on the way out the door. I obviously wanted him to stick around, and I think he’ll be a great, if not elite, player for the next couple years. But if he has all these questions and red flags surrounding him right now, what’s it going to look like in five years? Will he eventually need to shift to third, where his bat is unlikely to play? How will his declining power translate to one of most pitcher-friendly parks in baseball? These questions are why Bogaerts was not a “blank check” guy, and why it’s digestible to let the player go if not the person.


So where do the Red Sox go from here? My guess is as good as anyone’s, but one thing is for the certain: The Red Sox are trying to win. You don’t sign a 35-year-old closer to 16 million a year if you’re not expected to win. The question isn’t if the Red Sox are going to spend, but how and when. They are going to get a premier pitcher, whether by free agency or trade. They are going to get at least two bats, preferably right-handed ones. I would qualify it as unlikely that they go after Swanson or Correa, given that they have other holes to fill and depth in the minor league system, but you never know.


Regardless of what the Red Sox do, this is an inflection point in their history. Play your cards wrong this offseason and in Rafael Devers extension talks, and it’s going to be really hard to pull yourself back up. Yet there is still time, money, and most of all, urgency. As painful as the Bogaerts departure was, don’t write the Red Sox obituary quite yet.


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