The New York Yankees approach every season with a clear, singular goal. Any season that does not end in a World Series title is a failure. That's why it's so curious that GM Brian Cashman is willing to enter the 2025 campaign with such an imperfect roster.
In fairness to the team's front office, major injuries to both ace Gerrit Cole and slugger Giancarlo Stanton have substantially weakened the team. Stanton suffers an injury or two every season but the fact that he won't be ready for Opening Day could not have been anticipated. Cole's season-ending injury is even worse luck for Cashman and his franchise.
That does not mean the franchise did everything possible to compete with the likes of the Dodgers to win it all. Cashman deserves criticism for his inability to build a roster that even looks like a favorite to win the AL East. Here are the three missteps he'll regret more than anything else as the regular season rolls along.
1. Not addressing the third base issue
Even if everyone on the roster was fully healthy heading into Opening Day there would still be a major hole to fill at third base. Oswaldo Cabrera seems set to start the campaign as Boone's everyday starter at the hot corner but he's much better suited to be a utility player.
Signing Alex Bregman was the obvious baseball solution to round out Boone's infield but ownership refused to meet his contract demands. Cashman should be criticized for his failure to convince Hal Steinbrenner to open up his check book to land the former All-Star.
Even a trade for Nolan Arenado would have given New York a meaningful upgrade. The Cardinals are not in a position to ask for a big trade return given the veteran's advanced age and sizeable contract. There's still time for Cashman to swoop in for Arenado but there's no indication he's ready to do so at the moment.
The Yankees might find a way to succeed without a quality starter at third base but it places a lot of pressure on the rest of Boone's everyday lineup. Absent an in-season trade it looks like New York is punting on a position where power hitters are more the norm than the exception around MLB.
2. Not signing a dominant left-handed reliever
Trading for Devin Williams gave the Yankees a reliever with legitimate swing-and-miss stuff to deploy in the ninth inning. That was one of Cashman's best moves of the offseason.
Unfortunately, New York didn't follow that up by signing a southpaw reliever capable of racking up strikeouts in a setup role. Tim Hill is a quality pitcher but he gives up a lot of contact. Some of those ground balls have a way of finding their way through holes in the infield with runners on base.
Tanner Scott would have been a dream signing for the Yankees bullpen, but, like Bregman, he was judged to be too expensive. Andrew Chafin was another lefty who could have given Boone's bullpen a major boost.
There's still time for Cashman to correct this error by making a move at the trade deadline but there's no guarantee the Yankees will still be in the mix for a playoff berth. A more powerful left-handed arm could have helped Boone's team win several more games ahead of the deadline.
3. Letting Juan Soto get away
The moment the Yankees pulled the trigger on the trade that brought them Juan Soto they knew it would take a mammoth contract to retain him. Instead of paying what was necessary, New York let him move across town to commit his future to the Mets.
Some fans might give the Yankees credit for showing a measure of financial restraint, but it cost the team a generational superstar who could have anchored their lineup for years to come. It's hard to put a price on that kind of star power in one of the world's largest media markets.
It's hard to envision a scenario where the Yankees would have lost out on Soto if they had given him the largest contract offer. Instead, they came up short, and now their lineup is going to suffer. Cashman did a reasonable job of pivoting after losing the superstar slugger but the chances of him making up for Soto's absence by committee aren't great. Every time Soto hits one out of the park for the Mets it's going to sting Cashman to the core.