The Boston Red Sox keep rolling, even if the Adley Rutschman isn't able to suit up for them just yet. Craig Breslow's prized trade deadline addition is still recovering from a wrist injury, but the hottest team in baseball retained that label the day after the trade deadline with a 14-2 drubbing of the Chicago White Sox. Yet, it was worth noting that, in the offensive barrage by the Red Sox, that the only position that didn't accrue a hit on the night was catcher, Connor Wong to be specific. That's why the Red Sox were so aggressive in going out to trade for a three-time All-Star like Rutschman.
Make no mistake, though, Breslow and Boston paid an exorbitant price to land Rutschman. No. 2 prospect Anthony Eyanson, No. 4 prospect Kyson Witherspoon and No. 5 prospect Enddy Azocar was the heart of the return for Rutschman and veteran backup Jake Rogers. That price tag had many Red Sox fans bristling, saying the club gave up too much. Not only is that incorrect in itself, but it could be made even more so if Boston can get an extension done soon with Rutschman.
Extending Adley Rutschman is paramount for the Red Sox

Eyanson, Witherspoon and Azocar are all high-value prospects, make no mistake. Eyanson has dominated at High-A and Double-A this season, Witherspoon was a first-round pick last year, and Azocar is a toolsy High-A outfielder with immense upside. Yet, the Red Sox and Breslow are trying to win now, and Rutschman helps the team in Boston as soon as he returns. And with Boston's pitching infrastructure and development, the arms feel somewhat replaceable eventually.
That's why, from where I'm sitting, the trade is worth it now. But that, admittedly, is up for debate considering how you value win-now type of moves and the prospect capital given up to do so. Thus, it stands to reason that the only thing that would make it worth it for some fans is if the Red Sox ensure that Rutschman is with the organization well beyond the 1.5 seasons remaining before he hits free agency.
It's worth noting that, in the aftermath of the initial reports of the trade being close to finalized, a few hours passed before it was reported as a done deal. Jared Carrabis of Section 10, who was first to mention the close possibility of the trade, speculated on a trade deadline stream that the reason it took so long was that the Red Sox were putting out feelers with Rutschman about the possibility of an extension.
That's no guarantee that a deal will come, of course. However, if true, it does indicate that the Red Sox also see the value in an extension. And while some will talk about the surface numbers and injuries for Rutschman being a cause for concern about a possible long-term deal, the underlying numbers and what Boston gave up would suggest that they're still willing to go that route.
Such a contract won't be cheap, but the Red Sox are far more equipped to match that price than the Orioles were, clearly.
What an Adley Rutschman extension could cost the Red Sox

The idea behind an extension for Rutschman, beyond the obvious of making the investment even more ironclad in a star catcher, would be to buy out the 2027 season, his final year of arbitration, for the catcher and then extend him likely into his mid-30s. At 28 years old, maybe the best framework to work with would be something of a marriage between Cal Raleight's six-year, $105 million deal to buy out three arb years and Will Smith's 10-year, $140 million contract that bought out two years of arbitration.
Two things at play in the matter, however, are Rutschman's injury history and the fact that there simply aren't many star catchers in baseball. That makes comparisons a bit difficult, but where we land is likely something in the six or seven-year range with a bit of a higher AAV overall.
So what would that look like for the Red Sox and Rutschman? My best guess would be something along the lines of a seven-year, $140 million deal. They could buy out the 2027 arbitration for something like $12 million, which would then effectively make this a six-year, $128 million extension beyond club control, good for a $21.33 million AAV for the last six years of the deal.
Maybe that's a bit rich, but I'd prefer to be on that side in projections rather than underestimating. That's especially true given that we know the Orioles were unable to get a deal done, indicating that it might be expensive.
The good news for Boston, though, is that there are things working in their favor. Rutschman's ability as both a switch-hitter and elite defender make him exceptionally valuable. He doesn't have Scott Boras representing him, giving a better chance for a pre-free agency extension. And there are indications that the two sides both already have interest in a deal.
There are no guarantees, but with what the Red Sox paid, much of that fan base needs the organization to get the new contract done. And it seems like the arrow might already be pointing in that direction.
