Brian Cashman somehow got outsmarted by Craig Breslow with Max Fried signing

Game 1 of the ALWCS between the New York Yankees and the Boston Red Sox was a representation of the choices each had made. Brian Cashman looked on as his offseason decision took the mound. Craig Breslow did the same.

Both teams were in the market for top-of-the-rotation arms last offseason. They went about solving that need in different ways. Cashman chose to lavish Max Fried with the largest contract ever given to a left-handed starting pitcher. Boston wanted him, but Breslow ended up taking a different route. He dipped into his deep farm system to snag a different lefty, trading for Garrett Crochet in a swap of sock colors.

Of course, prospects, a price which Breslow paid handsomely, weren't the only expense for the Red Sox, who also had to sign Crochet to a six-year, $170 million extension. Advantage Cashman, right? We initially thought so, but not so fast.

Game 1 between the Yankees and Red Sox proves Craig Breslow outfoxed Brian Cashman

With the two aces dueling last Tuesday, the differences became apparent. No slight against Fried, he didn't allow a run over 6 1/3 innings, but it was Crochet who looked the part of a fire-breathing ace.

Yes, Anthony Volpe beat Crochet for a second-inning solo-homer, but from that point on, Crochet shut down the Yankee lineup, setting down 17 batters in a row before Volpe would end his streak with a single to center. In 7 2/3 innings, Crochet struck out 11, allowing just four hits and no free passes.

Fried, on the other hand, wiggled and squirmed in and out of trouble. He allowed four hits but issued three walks. He was in a two-out jam with runners on second and third in the fourth inning. Then he allowed two baserunners in the fifth. He issued his final walk in the sixth.

Maybe the traffic on the bases made Aaron Boone skittish when he pulled Fried after one batter in the seventh. It was the wrong call, but it's a plausible explanation for his thought process.

What we saw in this matchup was a true ace going up against a very high-end No. 2 starter. No disrespect to Fried, who turned in a superb 2025 campaign with a 2.86 ERA and 189 strikeouts in 195 1/3 innings, but Crochet bested him in every metric, posting a 2.59 ERA and leading the majors with 255 strikeouts in 205 1/3 innings.

In fairness, Cashman at the time thought that he would have Gerrit Cole anchoring his rotation. Objectively, Crochet is the better value. Boston's ace is 26 while Fried is 31. Despite the age discrepancy, Crochet cost nearly $40 million fewer in total.

The Yankees signed the Fried deal knowing it would end poorly. There have been a lot of contracts that haven't aged well in New York recently. DJ LeMahieu, anyone? Still, they looked at it as the cost of doing business.

Cashman might argue that the cost in prospects offsets the monetary discrepancy. However, prospects are far from a guarantee, and Cashman squandered some good ones for the likes of Jake Bird and Ryan McMahon. By the way, Ryan McMahon is only here because past bad contracts didn't allow Cashman to address the hot corner until the trade deadline.

New York might not have had as deep a farm system as Boston did at the time, but Cashman certainly could have scrounged up the necessary youngsters to get a deal done with the White Sox if he wanted to. He did not.

Now, he'll have to live with the decision, knowing that he opted for the lesser option without saving anything in the process. He'll have to stare down the reality that he was beaten by a guy who created the Rafael Devers controversy for no reason. That surely stings.