3 trades that destroyed the Yankees’ hopes of a World Series

frankie montas, yankees
Aug 18, 2022; Bronx, New York, USA; New York Yankees starting pitcher Frankie Montas (47) walks off the field after the top of the fifth inning against the Toronto Blue Jays at Yankee Stadium. Mandatory Credit: Brad Penner-USA TODAY Sports

The New York Yankees, despite their recent win over the Washington Nationals, find themselves far from playoff contention. As the team remains 17 games back in the AL East and 9.5 games behind in the Wild Card race, the struggles of the 2023 season have raised questions about their roster construction and strategic decisions made by general manager Brian Cashman.

“It’s been a disaster, this season,” he told reporters. “It’s definitely a shock. Certainly, I don’t think anybody on our side of the fence, from our player group, from our coaches, our manager, or even outside the organization, would’ve predicted this.”

Several trades and acquisitions have proven detrimental to the team’s aspirations, setting them back in their pursuit of success. In this analysis, we delve into three trades that have had a lasting negative impact on the Yankees.

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Three Trades That Spelled Doom for the Yankees: Analyzing Cashman’s Moves

1. The Josh Donaldson Deal: An Expensive Gamble

The trade that brought Josh Donaldson, Isiah Kiner-Falefa, and Ben Rortvedt to the Yankees stands as a glaring example of Cashman’s missteps.

Despite the team’s need for an upgrade, the acquisition of Donaldson, plagued by concerns about his clubhouse relationships, turned out to be a costly blunder.

josh donaldson, yankees
Jun 11, 2023; Bronx, New York, USA; New York Yankees third baseman Josh Donaldson (28) reacts after hitting a deep fly ball for an out against the Boston Red Sox during the sixth inning at Yankee Stadium. Mandatory Credit: John Jones-USA TODAY Sports

“The Donaldson trade was terrible. That was bad from the jump. I think the Donaldson trade was bad from the start because the Yankees knew just how poorly he was getting along with people in Minnesota. There was some toxicity going on there. I don’t think you can look at the Donaldson trade in any positive way.”

Via Jeff Passaon on the Michael Kay Show.

With two years and $50 million left on his contract, Donaldson’s performance has been abysmal. The aging player’s .142 batting average and .225 OBP this season reflect his decline, leaving the Yankees burdened by an unproductive and costly asset.

Kiner-Falefa, while versatile, has been inconsistent in both defense and offense. His .253 batting average, .318 OBP, six homers, and 35 RBIs illustrate his limitations as a starter. As the Yankees evaluate their options, IKF may continue as a utility player with value, but relying on him as a regular starter remains questionable.

Rortvedt’s promotion following injuries to other catchers showcases the lack of depth the Yankees faced. While his offensive contributions have been limited, his lefty bat might earn him consideration as a reserve player in 2024.

2. Frankie Montas and Lou Trivino: A Medical Oversight

The Yankees’ acquisition of Frankie Montas and Lou Trivino proved ill-fated due to a failure to recognize Montas’ existing shoulder injury. This oversight led to Montas missing the entire 2023 season. The trade, which involved leveraging pitching prospect potential, yielded disappointing results as Montas struggled and Trivino’s impact was minimized.

With Montas heading into free agency at age 30, the Yankees’ prospects of benefiting from the trade remain dim. Trivino, recovering from injury, poses further uncertainty for the team.

The Yankees traded one of their top pitching prospects in exchange for Montas and bullpen piece Lou Trivino. Cashman might consider bringing back Montas on a one-year deal after his injury, but relying on him to become a key rotation player is uncertain.

The Twins and Athletics trades indeed illustrate a scenario of misjudgment concerning the Yankees’ attempts to strengthen the roster. Trading prospects is a practice that has existed for a long time, but in recent years, the Yankees have consistently found themselves at a disadvantage in these transactions.

3. The Joey Gallo Trade: A Mental Challenge

Acquiring Joey Gallo aimed to bolster the Yankees’ offensive power, yet his performance fell far below expectations. Gallo’s .160 batting average, .303 OBP, 13 homers, and 38.6% strikeout rate raised concerns about his fit within the team’s lineup. His struggles were exacerbated by the intense media scrutiny and pressure that playing in New York entails.

While the Yankees gained pitcher Clayton Beeter in the Gallo trade, his contributions failed to offset the offensive shortcomings that hindered the team’s World Series aspirations.

In Retrospect

Cashman’s trades have not yielded the desired results, and the Yankees’ struggles in recent seasons underscore the impact of these missteps.

As the team navigates a challenging competitive landscape, a reevaluation of their approach is imperative. The Yankees must consider nurturing their young prospects, who have the potential to inject new energy and enthusiasm into the roster. By learning from the successes of teams like the Tampa Bay Rays, the Yankees can make strategic adjustments to reinvigorate their pursuit of excellence and regain their competitive edge.