Another overlooked Brian Cashman miss arguably cost Yankees 2024 World Series

Following the 2021 season, which was one of the worst start-to-finish "contending" campaigns the New York Yankees (or really, any other team) has had in the modern era, Brian Cashman needed to upgrade the roster and work on cleaning house.

He did ... not that. Or, at least he thought he was doing that when he traded for Josh Donaldson and Isiah Kiner-Falefa, got rid of a fan-favorite (and team favorite) Gio Urshela, continued wasting time with Aaron Hicks, Domingo Germán, Joey Gallo and Aroldis Chapman, and re-signed Anthony Rizzo.

That last one was probably the least egregious, but it once again represented a scenario in which the Yankee were settling for less. That offseason, all of Freddie Freeman, Corey Seager, Kyle Schwarber, Carlos Correa, Marcus Semien, Justin Verlander, Kevin Gausman, Max Scherzer, Starling Marte, and others were available for the taking.

The Yankees signed none of them, and prioritizing Rizzo over Freeman when all was said and done could've perhaps been the biggest mistake. Some might point to neglecting the pitching or the shortstop position, but all in all, the Yankees' pitching has gotten the job done over the last three years and the organization felt strongly about hitching their wagon to Anthony Volpe, which could work out still (or make them regret everything).

It's unclear if Freeman wanted to come to New York, but when the dust settled and he agreed to a six-year, $162 million contract with the Dodgers (the same contract Carlos Rodón got!!), it felt more and more like a gigantic miss, especially since the Yankees have paid Rizzo over $60 million since the 2021 trade deadline.

Meanwhile, Rizzo's career is essentially done and Freeman just won World Series MVP. Think that extra $100 million for an additional three seasons would've been worth it for a team that could afford it? We think so too.

Another overlooked Brian Cashman miss arguably cost Yankees 2024 World Series

Maybe the price was cheaper because Freeman wanted to return to his native Southern California. Maybe the Yankees didn't try as hard. We'll never really know. But the lack of intensity surrounding the pursuit leaves much of this open to interpretation and further criticism.

And though there are conflicting details, we tend not to give the Yankees' front office the benefit of the doubt because their success rate with free agents and trades has taken a steep decline over the last 15 years.

From the outside looking in, Rizzo's career was very clearly on the back nine, and the Yankees saw an opportunity to import a veteran at a discounted price, their favorite thing to do. And they might've been too tantalized by what he offered in 2021 because of how troubling their first base problems were with Luke Voit and Mike Ford.

In the end, the 2024 World Series plainly laid out what we knew all along. The Dodgers went the extra mile to acquire so many players the Yankees were also interested in acquiring. Freeman, Yoshinobu Yamamoto, Tommy Edman, Michael Kopech, Jack Flaherty and Kiké Hernandez. LA got all of them while the Yankees were forced to pick up the pieces multiple times after losing out and making worse pivots to address their needs.