Brian Cashman's Best Trade Deadline Move Might Be One Yankees Fans Least Expect

New York Yankees general manager Brian Cashman is pondering his options ahead of the MLB trade deadline.

New York Yankees general manager Brian Cashman before game one against the Los Angeles Dodgers the 2024 MLB World Series at Dodger Stadium. | USA TODAY Sports via Reuters Connect

Time for a history lesson. In the 1985 movie "Brewster's Millions," Richard Pryor is tasked with spending $30 million in 30 days. Part of that plan included running for mayor of New York City and calling for the voters to elect none of the above on the ballot. That's what Yankees general manager Brian Cashman should do ahead of Monday's trade deadline.

New York is being linked to just about every big name on the trade market, including Detroit Tigers ace Tarik Skubal, San Diego Padres closer Mason Miller, and Colorado Rockies catcher Hunter Goodman.

Recently, there's been a wave of reports calling for the Yankees to trade for an outfielder after Cody Bellinger landed on the injured list over the weekend.

But Cashman's best move? None of the above. Here's why.

Why none of the above?

First, imagine what the Yankees lineup could look like in September if Bellinger, right fielder Aaron Judge, and designated hitter Giancarlo Stanton return from the injured list. You are talking about three former MVPs, and there's no one on the trade market who can top that kind of production.

New York Yankees designated hitter Giancarlo Stanton (27) celebrates his three-run home run against the Seattle Mariners with center fielder Cody Bellinger (35) and right fielder Aaron Judge (99) during the sixth inning at Yankee Stadium. | IMAGN IMAGES via Reuters Connect

Second, if the trio doesn't return for the stretch run, the Yankees aren't winning the World Series. That's just a cold, hard fact. So why start selling off top prospects before the deadline just for a long shot at a title? Cashman would be better off holding onto his best trade chips and focusing on 2027.

Seller's market

Third, Cashman isn't dealing from a position of strength. Everyone knows the Yankees are desperate for upgrades. And they aren't the only contender looking to make a move. It's a seller's market, and New York will have to overpay dearly to bring anyone to the Bronx.

Fourth, keep in mind that the Yankees still sit atop the American League Wild Card standings heading into Tuesday night and are just 2.5 games behind the first-place Tampa Bay Rays in the AL East.

Is it difficult sometimes to watch the lineups manager Aaron Boone is forced to field? Absolutely. But like it or not, the Yankees have been doing more than just treading water even though Stanton has been out since April and Judge has been sidelined since the end of May.

Yankees are winning arms race

Nonetheless, if the Yankees are going to go anywhere this fall, it will be on the back of the team's pitching staff. Gerrit Cole and Max Fried are rounding into form after IL stints. Carlos Rodon and Clarke Schmidt are expected back sooner rather than later. And Cam Schlittler remains a Cy Young Award candidate. Add all that up, and you get a staff that leads the majors with a 3.41 ERA.

Jul 25, 2026; Philadelphia, Pennsylvania, USA; New York Yankees pitcher David Bednar (53) throws a pitch against the Philadelphia Phillies during the ninth inning at Citizens Bank Park. Mandatory Credit: Bill Streicher-Imagn Images | IMAGN IMAGES via Reuters Connect

And it's not just the starters who are getting it done. The Yankees are second in the majors with a team bullpen ERA of 3.07, thanks in part to closer David Bednar, who's fifth in the AL with 21 saves. The right-hander hasn't allowed a run since May 18. That's 20 consecutive scoreless appearances. Not too shabby.

So let Cashman go out and pick up a cheap band-aid option like Kansas City Royals outfielder Lane Thomas. But he must resist the temptation to sell the farm and go all-in ahead of the deadline. There's not much out there that will improve the Yankees' postseason odds, and whoever he can acquire will come with an insane price tag.

Yankees' postseason odds still looking good

Despite the struggling offense, FanGraphs gives the Yankees a 98.7% chance of making the playoffs. And New York has a 12.2% chance of winning the World Series. The only club with better title odds is the Los Angeles Dodgers (24.3%).

Think about that. The Yankees, despite all their glaring needs and shortcomings, remain the favorite to represent the AL in the World Series.

So let the Yankees dink and dunk their way through the dog days of summer. Cashman must resist the temptation to wheel and deal. If Judge, Stanton, and Bellinger can return before the postseason, the Yankees are in position to win their first championship since 2009. If the trio doesn't return, well, then this just isn't the year.