The Yankees made 2 franchise-altering busted trades

frankie montas, yankees
Aug 18, 2022; Bronx, New York, USA; New York Yankees starting pitcher Frankie Montas (47) reacts during the second inning against the Toronto Blue Jays at Yankee Stadium. Mandatory Credit: Brad Penner-USA TODAY Sports

Over the past two years, the New York Yankees and General Manager Brian Cashman have executed two severely misjudged trades, putting misplaced faith in older and injury-prone players.

Failed Strategies: Ill-advised Trades and Creative Misfires

The Yankees attempted to think outside the box by strengthening the starting rotation and opting for an aging veteran at the hot corner. However, these transactions have left a significant blemish on the team’s strategic blueprint. With no major acquisitions at the recent trade deadline, it’s evident that the Yankees are determined to play out the rest of the 2023 season with their current roster—a roster that has proven inadequate.

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The Yankees misfired significantly on two trades:

1.) The Frankie Montas Debacle

The decision to acquire Frankie Montas from the Oakland Athletics stands out as one of the most regrettable moves in Cashman’s tenure.

Despite Montas’ impressive 3.18 ERA over 104.2 innings with Oakland, he recorded a lackluster 6.35 ERA across 39.2 innings for the Yankees before ultimately undergoing shoulder surgery. Reports later revealed that Montas wasn’t fully fit when the Yankees acquired him, suggesting a failure in medical assessment.

The Yankees sacrificed one of their top pitching prospects for a player who hasn’t pitched an inning this year and likely won’t for the rest of the season. Heading into free agency in the upcoming off-season, Cashman essentially traded a promising minor leaguer for a player who had a negative impact and contributed nothing to the rotation.

With both Montas and Luis Severino becoming free agents this winter, it’s plausible that both will sign with other teams as the Yankees aim to reset and craft a strategy that isn’t dependent on injury-prone players.

2.) The Josh Donaldson and Isiah Kiner-Falefa Misstep

In trading for the then 36-year-old Josh Donaldson, the Yankees’ real goal was to secure a shortstop in the form of Isiah Kiner-Falefa.

Unfortunately, both players fell short of expectations, with Donaldson having two disastrous seasons. In 2022, he managed just .222 with a .308 OBP over 132 games. This year, despite hitting 10 homers in 34 games, his record stood at .142 with a .225 OBP and a 75 wRC+, the lowest of his career.

In essence, the Yankees traded for an aging starter and a supplemental player who morphed into an underperforming utility outfielder.

In return, the team let go of Gary Sanchez and Gio Urshela. Although Sanchez turned out to be a disappointment, Urshela hit .285 with a .338 OBP, 13 homers, and 64 RBIs last season before his promising run was cut short by injury.

The Yankees were saddled with $50 million from Donaldson’s contract, while Montas, expected to be a key part of the rotation, ended up merely occupying a spot on the injured reserve.

Cashman’s Underwhelming Trade Track Record

At this juncture, it’s clear that Cashman hasn’t executed a truly successful deal in quite some time. The accumulated result of these flawed transactions has led to one of the most underperforming rosters in Major League Baseball, despite the Yankees boasting one of the sport’s highest payrolls.