Yankees Trade Deadline 2023: Brian Cashman's failure to strengthen $279,000,000 roster draws heavy criticism from insider

As the Aug. 1 deadine approached, New York Yankees general manager Brian Cashman was faced with two options: add to a roster that that was in the hunt for the playoffs or move on from some of the team's hefty and underperforming contracts. He opted for a third option.

At a critical stage of the season, the Yankees front office froze. While some of their American League rivals added big-name stars, the Yankees chose to remain relatively inactive.

Brian Cashman's last minute moves for pitchers Keynan Middleton and Spencer Howard did little to appease a fanbase that has been pleading for changes.

In a recent article, Chris Kirschner of The Athletic provided his views on the Yankees' baffling deadline strategy:

"They mostly stood pat, which was the worst course they could’ve taken. This was a failure by Brian Cashman and the front office"

MLB reporters Kirscher and his colleague Brendan Kuty went on to provide F ratings for New York's deadline, calling it a "disaster." They argued that the management showed little direction and failed to solidify the roster for the 2024 season.

Yankees GM Brian Cashman addresses the Yankees approach to the Trade Deadline.

#YANKSonYES pic.twitter.com/8lm3w4npDq

"Yankees GM Brian Cashman addresses the Yankees approach to the Trade Deadline. #YANKSonYES" - YES Network

Many expected the club to focus on bolstering an offense that currently ranks 29th in the MLB in batting average (.229), 29th in hits (804) and 23rd in team OPS (.703). Instead, Cashman decided to sign two relievers.

Brian Cashman and the Yankees are at risk of missing out on the playoffs for the first time since 2016

Luis Severino of the New York Yankees is pulled from the game by Manager Aaron Boone at Yankee Stadium

There were high expectations this season for a Yankees team that started the year with the second-highest payroll in the majors. Their $279 million payroll was behind only the New York Mets, per Spotrac.

After last night's 5-2 loss to the Tampa Bay Rays, the Yankees have dropped to 55-52 on the season. They are currenly in last-place in the AL East and trail the division-leading Baltimore Orioles by 11 games. More concerning for the organization is that it is now 3.5 games out of the last wild card spot.

Aaron Judge discusses the 5-2 loss, Yankees trade deadline moves, and more. pic.twitter.com/9X9GpGI4Yr

"Aaron Judge discusses the 5-2 loss, Yankees trade deadline moves, and more." - YES Network

While the Yankees have decided to trust their current group, other teams upgraded before the deadline. Justin Verlander returned to the Houston Astros. The Los Angeles Angels traded for Lucas Giolito, Reynaldo Lopez and C.J. Cron. Max Scherzer signed with the Texas Rangers.

All three of those teams could find themselves in a battle for one of the remaining wild card positions with the Yankees late in the season.