3 Brian Cashman mistakes who are about to beat the Yankees in World Series

There have been many heroes for the Los Angeles Dodgers en route to a 3-1 World Series lead over the New York Yankees. Starting pitcher Jack Flaherty was sensational in Game 1, keeping the Yankees' bats at bay long enough for his offense to finally come to life. Speaking of that offense: Freddie Freeman has been a man possessed, winning Game 1 with a walk-off grand slam and then homering in Games 2, 3 and 4 to boot. And Yoshinobu Yamamoto delivered a gem of his own in Game 2, pitching L.A. to a big victory.

But all three of those names have more in common than helping Los Angeles get within one win of a ring. All of them, at one point or another, appeared close to becoming members of the New York Yankees — that is, until Brian Cashman got in the way.

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3. Swinging and missing on Freddie Freeman

The man currently terrorizing Yankees pitching was once on the team's radar as a free agent. Back in the winter of 2021, Freeman was the top first baseman on the market, and New York just so happened to have a glaring hole at the cold corner. There was just one problem: Cashman was never quite able to gain any traction with the former Atlanta Braves star. Freeman only ever seriously considered the Braves and Dodgers, telling the New York Post's Jon Heyman that “I had a conversation with [Cashman]. They never made an offer."

New York has been looking for consistent offensive production at first ever since, while Freeman has just kept on hitting — especially in this series, where he's almost single-handedly carried the Dodgers to a 3-1 series lead. Maybe Freeman was only ever willing to sign with Atlanta (the only organization he knew) or the Dodgers (his hometown team); but Cashman certainly doesn't seem to have helped matters, and the Yankees are still feeling the consequences.

2. Turning down a trade for Jack Flaherty

Flaherty, on the other hand, was very nearly a Yankee. It's an open secret at this point that Cashman had reached an agreement with the Detroit Tigers on a trade sending the right-hander to New York at this year's trade deadline. There was just one problem: The Yankees found an issue with Flaherty's medicals, and it was a big enough concern that Cashman decided to call the deal off entirely. Flaherty does have a lengthy injury history, but he hasn't shown it this season, excelling for L.A. down the stretch of the regular season and showing out in Game 1 of the World Series against the Yankees. Rather than relying on unproven younger pitchers like Clarke Schmidt and Luis Gil, New York could've slotted Flaherty behind Gerrit Cole and Carlos Rodon.

1. Not ponying up for Yoshinobu Yamamoto

This might be the one that hurts the most. Yamamoto was as much of a slam dunk as a pitcher who's never played in the Majors could possibly be: The righty had won Japan's pitching triple crown in each of the last three seasons, and at 25 years old, he was just entering his prime. With the Yankees, Dodgers and New York Mets invonlved in the bidding, among others, everyone knew it was going to take a big chunk of change to land him. Los Angeles was willing to pay that price, eventually signing Yamamoto to a 10-year, $325 million deal. New York, at least if reporting is to be believed, was not: Cashman reportedly stopped at $300 million, with rumors circling that he didn't want to hand out a contract higher than the one he gave to Cole in 2019.

Maybe that was Steinbrenner's decision, and maybe it was out of Cashman's hands. But after Yamamoto looked every bit like the ace that was promised in the Dodgers' Game 2 win, it looks like yet another in a long line of errors that have left New York with an uphill climb in this World Series.