I feel like I’m taking crazy pills with this whole Xander Bogaerts situation. Listen, I love Bogey as much as any other Bostonian. He’s been one of my favorite players ever since he got called up to The Show in 2013. Likewise, he’s been one of the best contact hitters in the league over the past few seasons, and while his defense at shortstop hasn’t been incredible, he’s made plenty of strides. Most importantly, though, as the longest tenured player on the team, Bogaerts is an invaluable leader in the clubhouse.

This is why I want Chaim Bloom and co. to reach some sort of agreement with the star shortstop. Bogaerts will almost certainly opt out of his three year, $60 million contract this offseason, which is a bargain considering his value. He’ll test the open waters, though the Sox will have an opportunity to restructure his deal before he hits the market. 

“Ok, well, just get that crap done already,” some of you may shout. And I agree. Get it done. But…there’s a chance this extension could seriously screw the Sox over a few years from now. Like ‘Why did I leave my midterm paper for the final day’ levels of screwed. Chaim needs to play his cards carefully here, and I don’t think enough Sox fans understand just how tenuous this situation is. 

There’s a real timeline out there where the 30 year-old Bogaerts receives a David Price-esque albatross of a contract. If that happens, I just hope it’s a bummy team like the Cubs. For reference, the Sox shit out a seven-year, $217 million stinker of a deal for Price in 2016, who entered free agency at the same age as Bogaerts is now. There’s a difference between wanting Bogaerts back and not being okay with that kind of contract being handed out. The price has to be right, pun intended. With Price, obviously he helped win us the World Series in 2018, but he clearly did not live up to his price tag. After all, the Dodgers had to take on half of his contract as a poison pill when they acquired Mookie Betts in 2020. And guess what? Price is finally off the Sox’s books this offseason. I guess we really did pay our price, huh. 

Consider that a word of caution. If Bogaerts gets a similarly structured deal, things might get ugly for the Sox. There’s little chance Bogie produces at the clip of a $30 million dollar shortstop for four more years, let alone seven or eight. There’s no doubt he’s an elite shortstop right now, but that kind of longevity both at the plate and on the field for the position is rare (see: Jeter, Derek). Also, there’s little to no precedent of an aged SS like Bogaerts getting the years or guaranteed salary that the X-man could garner. Marcus Semien (who turned 32 this September) signed a massive seven-year contract last year with the Rangers, and well, he’s not even a shortstop anymore. That could be an issue with Bogaerts. He’s never really had the defensive range for SS, and while it improved this season, he will  be a liability if he stays there long-term. My guess: he’ll be a second baseman for whatever team he’s on by the 2024 season.

But what about his hitting? Aside from Rafael Devers, he’s the second-best hitter on the team and easily the most consistent one. If he leaves this offseason, the Sox will surely miss his production. However…it looks like his best days at the plate are in the past. He’s not gonna get any better, and his power numbers already look to be on the decline. His ISO percentage, which measures just extra-base hits to the proportion of at-bats, was his lowest mark since 2017 at 0.149 and was nearly 50 percentage points behind his total last year. Sounds like a pretty bad omen to me.

If I had to make a prediction, I don’t think Bogaerts will be on the Sox next April. His asking price seems too high for the amount of years he’ll likely want. After all, a restructured three or four year deal with a higher AAV would send him back to free agency in his mid 30s, where his market would be vastly reduced. This is his only chance at a major contract. Also, keep in mind that Bogaerts is a Scott Boras client, so anything less than the top dollar will not suffice. Unfortunately for the Sox, they’d be mistaken to agree to a long-term deal. On the other hand, he is a fan and clubhouse favorite, and letting him go would severely mess with both of those dynamics. It really sucks. A winning solution for both sides seems really unlikely at this point, though maybe I’m being too negative and something will get worked out. I don’t know. I will say, if Bogaerts leaves, it’s been one hell of a run. From winning it all as a rookie in 2013 to being the leader of the 2018 championship team, Bogaerts has left his mark on everyone who calls Fenway home.