Cheap John Henry may have already given up hope of an extension for Garrett Crochet

The Boston Red Sox traded four of their top-15 prospects per MLB Pipeline for Chicago White Sox ace Garrett Crochet on Wednesday. The best of the bunch was catcher Kyle Teel, who some within the Red Sox organization believe is their best catching prospect since Jason Varitek.

Crochet shined in his first season since he transitioned from a relief pitcher to a starter. He had over 200 strikeouts and a 3.58 ERA, and was one of the lone bright spots for a White Sox team which lost over 120 games. Chris Getz has kept no secrets about his intent to trade Crochet – and perhaps soon Luis Robert Jr. – for prospects as part of an all-out rebuild. His timing couldn't have been more perfect at the Winter Meetings, as the Red Sox missed out on two of their pitching free-agent targets in Blake Snell and Max Fried.

While acquiring Crochet is a big step for John Henry and Craig Breslow, the next step is determining when (or if) to give the left-handed ace a long-term extension.

A Garrett Crochet extension with the Boston Red Sox is no guarantee

Crochet's contract runs through the 2026 season, so there is no huge rush, but the longer Boston waits the higher his price tag could get. Ken Rosenthal of The Athletic reported the Red Sox may have some hesitancy about extending Crochet this early:

"After getting burned on nine-figure contracts for Sale and David Price, Red Sox owner John Henry is reluctant to award long-term deals to pitchers, according to sources briefed on his thinking. Perhaps his hesitancy will extend to an extension for Crochet, who is under club control for two more seasons. But the Red Sox are so deep in young talent, that they cannot possibly fit all of their prospects onto future 26-man rosters. So for them, Wednesday’s trade for Crochet was a move that made perfect sense," Rosenthal wrote (subscription required).

This is rather surprising from Rosenthal, as Henry has shown a willingness to spend this winter. The Red Sox were in the bidding for Juan Soto, and went as high as $700 million. Of course, spending on a proven position player talent like Soto is different than taking a relative gamble on Crochet. Boston's position on this matter is always subject to change, especially if Crochet pitches lights-out atop the Red Sox rotation this season at Fenway.

It's a precarious position for the Red Sox to be in. The longer they wait, the higher Crochet's price tag could go up. If they act now and sign Crochet to an extension, there's always a chance he doesn't pan out given his limited experience as a starting pitcher. Henry only has so much money to go around.