Negotiations on a new contract extension between Xander Bogaerts and the Red Sox didn’t result in a deal prior to Opening Day, and at the time, Bogaerts implied that the opener was an unofficial deadline.  “I’ve got a season coming up in front of me and I don’t want to put any of our teammates in that type of distraction,” Bogaerts said. “They don’t deserve it.  We had time to get something done. It didn’t work out.”

Now, Bogaerts has left the door slightly open for more talks during the season, telling The Boston Globe’s Peter Abraham that “I don’t know how this would work. But if they talk to [agent Scott Boras] behind closed doors and it’s something that’s fair, he can come to me.  We’ll see how that goes.”

Most players set Opening Day as the endpoint for any contract negotiations, echoing Bogaerts’ point that once games begin, the focus is solely on baseball.  (Even in Bogaerts’ proposed scenario, he would himself seemingly have no role in active talks.)  Most extensions that are announced during the season tend to be announced perhaps within the first few weeks, indicating that the two sides had things mostly finalized aside from a few small details.

That said, it isn’t uncommon for extensions to be struck during the season.  2021 alone saw multiple deals finalized well into the year, including extensions involving the Red Sox (their two-year pact with Matt Barnes) and another Boras Corporation client (Jonathan Schoop, who inked a new deal to stay with the Tigers).  However, all of those extensions were for significantly shorter terms and for less money than what Bogaerts is undoubtedly looking for in a new contract.

Bogaerts is already under contract via a prior six-year, $120MM extension signed in April 2019.  The shortstop can opt out of that deal after the season, leaving behind the $60MM he is guaranteed between 2023-25 plus a $20MM vesting option for 2026.  There is little doubt that Bogaerts will indeed opt out and hit the open market, as entering his age-30 season, the three-time All-Star could triple the $60MM he’d be leaving on the table in Boston given how this past offseason raised the bar for shortstop contracts.

With the larger shortstop market in mind, perhaps the key point in Bogaerts’ quote is “something that’s fair.”  Reports have suggested that the Red Sox made a curiously low offer to Bogaerts’ camp, with the team proposing to extend the term by just one guaranteed year — Bogaerts would earn around $30MM for the 2026 season, and still be paid $20MM for each of the next three seasons.  Boston’s proposal apparently didn’t get a response from Bogaerts and his reps, and one friend of Bogaerts described the offer as “a slap in the face.”

It could be that the Red Sox were simply starting low as a negotiating tactic, and as Abraham notes, team president Sam Kennedy and chief baseball officer Chaim Bloom have said that the Sox want to retain both Bogaerts and Rafael Devers (who is a free agent after the 2023 season).  That said, the Red Sox also signed Trevor Story to a big six-year, $140MM free agent deal, and the team has one of the game’s top shortstop prospects in Marcelo Mayer.  Between Story, Mayer, and the lowball offer, it would seem like the Sox are already preparing themselves for life beyond Bogaerts, unless he happened to take that below-market extension.

While Boras has a reputation for pushing his clients towards free agency, several high-profile Boras Corporation clients have indeed signed extensions over the years — even Bogaerts himself re-upped with the Sox entering his final year under team control.  Of those deals, however, Stephen Strasburg’s 2016 extension with the Nationals is the only big-money, multi-year pact signed in-season, and Strasburg and the Nats were much closer in talks than Bogaerts and the Sox seem to be at this point.

With Bogaerts this close to the open market, it would seem like the Red Sox would have to (if anything) overpay to prevent him from opting out.  The other factor involved is Boston’s mediocre start to the 2022 season, as with only a 13-21 record thus far, there has already been whispers that Bogaerts could be a deadline trade chip rather than a future cornerstone.  If the Red Sox continue to struggle and lean towards becoming deadline sellers, it could be that the Sox might take the approach of revisiting extension talks with Bogaerts around the All-Star break, and if a deal can’t be struck, the team would then focus on trading him.