1 NY Mets habit Brian Cashman should learn, 1 Yankees habit for David Stearns to copy

At the outset of the 2025 season, both the New York Mets and the New York Yankees had dreams of World Series rings. After the heat of the Juan Soto bidding war had died down, both fanbases fantasized about October victories with the prospect of a Subway Series to determine it all, further electrifying the city.

Of course, the best laid plans of mice and men often go awry. The Mets didn't even make it to October. As for the Yankees, their run was cut short prematurely by the division rival Toronto Blue Jays.

Both teams feature massive payrolls, but their architects, David Stearns for the Mets and Brian Cashman for the Yankees, have gone about building their teams in slightly different ways. While there is no one-size-fits-all approach, both executives would be wise to take a page out of the other's book as the offseason gets underway

One thing Brian Cashman can learn from the Mets and David Stearns is not to go overboard for good-not-great players

Fifteen-year, $765 million contract to Juan Soto notwithstanding, Stearns draws a line in the sand when it comes to his negotiations. This is especially true for players who, while good, are not bona fide superstars.

Case in point, Stearns had no problem staring down Pete Alonso in free agency last year. The easy play would have been to re-offer Alonso the seven-year, $158 million extension that he declined when Billy Eppler was running the show. At the time, Alonso thought he could get more, but a so-so 2024 hurt his market value.

The two-year, $54 million pillow contract that paid Alonso a hair over $30 million for 2025 and was looking at a pay cut for 2026 if he hadn't decided to opt out. The decision puts the ball back in Stearns' court, but now, with another year of data, Stearns can be more confident in a long-term commitment.

The flip side of what Stearns did with Alonso last year was to increase the Mets' luxury tax bill based on the short-term nature of the deal. Had he offered Alonso something along the lines of what he had previously rejected, the AAV (used for luxury tax calculations) would've been roughly 22.6 million. Instead, the actual number was $27.1 million. When paying the "Cohen Tax," the nearly $5 million difference isn't chump change.

This is where Brian Cashman falls short. The Yankees are more concerned with the top-end of the tax than the Mets are, and it shows in how he handles contracts and extensions for the players who are good, but aren't superstars.

A perfect example of this is the deal Cashman gave D.J. LeMahieu ahead of the 2021 season. LeMahieu first landed in the Bronx in 2019 and hit .327 with 26 homers, earning an All-Star selection and finishing fourth in the AL MVP voting. He'd follow that up in the pandemic-shortened 2020 season with the second batting title of his career, hitting a ridiculous .364.

LeMahieu was 32 when he was due for an extension, and Cashman lavished him with a six-year, $90 million deal that would take him through his age-38 season, which seemed to be a couple years two long for a contact hitting middle-infielder.

Cashman's logic was this: by extending the deal out over six years, he would pay a little more in total contract value than, say, a three or four-year deal, but the AAV would be much less, lowering the tax bill the Yankees would face.

Fast forward to today, and DJ LeMahieu is no longer a member of the New York Yankees, though they'll be paying him $15 million on their 2026 books, further handcuffing them to build the roster they want while avoiding the exorbitant tax penalties.

This isn't the first time Cashman has made this move either. The 2025 club was hamstrung by deals that were longer than needed. In addition to LeMahieu, old friend Marcus Stroman had quickly proven that he wasn't worth the $18 million the Yankees were paying him, and worse yet, when their rotation suffered injuries in spring training, the club didn't want to use him for fear of triggering a vesting option for 2026. That option was another mechanism to keep the AAV down, but it nearly blew up in their faces.

Additionally, their books were saddled with $10.8 million due to Aaron Hicks, who last played for the club in 2023. All of this mental gymnastics to avoid the tax man cost the Yankees, as they entered the regular season without a solution for third base, and then made a panic trade for Ryan McMahon at the deadline.

The lesson from Stearns should be clear. It's better to take your medicine now and play a fair rate for the appropriate amount of time than it is to get cute and try and avoid the consequences. It's just always so much worse when you pussyfoot around.

David Stearns and the Mets should take note of this Brian Cashman strategy and pay big for bona fide aces

One of David Stearns' most aggravating habits is refusing to pay for a true ace to lead the rotation. Blake Snell, Corbin Burnes, and Max Fried were all sitting there for the taking last year, and Stearns instead decided to sell Sean Manaea as the leader of the rotation.

As good as Manaea was in 2024, his track record shows that as a bad bet, and while most Mets fans wouldn't have bet that he would be pitching out of the bullpen come September, they all hoped for something more at the top of the rotation.

On the other side of town, Brian Cashman relishes the opportunity to make big splashes for fire-breathing aces. He came away last offseason with Max Fried, who certainly looked the part with a 2.86 ERA over 195.1 innings. In signing Fried, Cashman awarded him the largest contract ever for a left-handed starter in history.

That wasn't the only time Cashman struck, however. Before Yoshinobu Yamamoto broke his record, Gerrit Cole's nine-year, $324 million deal, authored by Cashman, was the largest ever given to a starter back in 2019.

A little more than a decade earlier, Cashman handed out another then-record contract to Hall of Famer C.C. Sabathia. The epitome of an ace in every way, Sabathia went out and led the Yankees to a World Series title in 2009, just as the ink was drying on his seven-year $161 million pact.

One could argue that a one out of three success rate isn't the greatest, but Cashman went into spring training this season with the idea of having a two-headed monster in Cole and Fried at the top of his rotation. An unfortunate UCL tear for Cole derailed that vision before it could get off the ground, but the Yankees will have another go at it in 2026.

While the Mets have an exciting young trio in Jonah Tong, Brandon Sproat, and Nolan McLean, their rotation was in tatters at points in 2025, and it would be lovely to have a battle-tested ace to help lead the charge for the youngsters.

Injuries are an unfortunate part of life, especially for pitchers, but as 2025 showed us, skimping on talent for that fear leads to wasted money nonetheless. After all, who really wants Frankie Montas on the club next season?

Stearns needs to start taking these types of swings for these types of players. The market isn't great this time around with Framber Valdez, Dylan Cease, and Zac Gallen representing a top-tier that has more warts than normal.

Still, sooner rather than later, Stearns will need to add a true rotation anchor to his collection if the Mets are going to break a title drought that is going on 40 years