Should Yankees general manager Brian Cashman be on the hot seat?

The Yankees’ season has ended, and while a fourth straight trip to the playoffs would be considered a major success for many franchises, it does feel that way in the Bronx. Heading into the season with massive expectations, the Yankees have not been able to take that next step since their ALCS run in 2017. Did general manager Brian Cashman leave himself vulnerable through his moves—or lack thereof—and could an incredible reign at the head of the Yankees’ organization be coming to a close over the next few weeks?

Cashman took over the job of Yankees general manager in 1998, during one of the great runs in baseball history. While detractors have given credit to his predecessor Bob Watson for much of the Yankees success in those early years, they leave out key moves that he made during each of those championship runs.

Since bringing home the World Series in 2009, he has been unable to put a team together to win the pennant. His rapid rebuild in 2016-2017 earned him the praise of many, but it is still pointed out that he has tremendous resources to work with and cover his mistakes.

This last offseason Cashman landed a prize in Gerrit Cole, a player he described as his “white whale.” Committing $324 million to one of the best pitchers in the game is the type of move you make to finish a championship roster. Anything short of elite results from the team can leave the big splashy move in question. Cole delivered this season, and was strong in the postseason, but the team did not reach its lofty goals finishing as the fifth seed in the American League.

It was clear that the Yankees had some holes in the roster approaching the trade deadline, yet the Yankees chose to not make any moves. No pitching help came for either the bullpen or the starting rotation, as Cashman said that the trade market was risky and uncertain.

The end result was a bullpen that struggled for stretches and looked to be missing injured reliever Tommy Kahnle from a depth standpoint. We will likely never know what other teams were asking for, but the Yankees were unwilling to part with their serious prospects for an upgrade in 2020.

Results speak volumes, the Yankees did have the best record from 2010 to 2019 going 921-699 during the decade. Despite that the Yankees did not make an appearance in the World Series and often did not feel like a serious threat to win when matched against the best teams in the league in the middle part of that stretch.

While Cashman has hit on buy-low players (Luke Voit, Mike Tauchman, Aaron Hicks), he has missed on many of his flashier trades. He brought in Sonny Gray while the Astros landed Justin Verlander and the World Series title. Gray told CC Sabathia on the R2C2 podcast last offseason that he realized the Yankees were behind on pitch technology and data once he arrived. While the team has taken dramatic steps to catch up in these areas and is now among the most savvy teams in the league, could the organization be looking for a GM that will get out in front of the next technology or player development strategy before it is too late?

The Yankees have major decisions to make this offseason as three of their starting pitchers head to free agency, along with the AL batting champ. The decisions made over the next three months will affect the Yankees’ organization for years to come.

Rivals to the Yankees are coming. Toronto has a load of young talent, and likely room to spend. Tampa using a low revenue model has played the Yankees tough for the last several seasons and won the AL East title this season. Members of the Rays front office have also moved on and exported a successful system for the Los Angles Dodgers who have become the class of the National League.

Boston recently hired another alumni of the Chaim Bloom to take over as the Chief Baseball Officer Baseball and many in the league think that Boston will rebound in the next couple of years to create a system that is competitive year-in and year-out, similar to the Dodgers.

Despite Houston’s cheating scandal and losing the top two Cy Young finishers from 2019 was able to punch their ticket back to the ALCS. The team that was built with a progressive methods that were not bound by tradition. Their front office tactics have also moved to the AL East as Mike Elias heads into his third offseason attempting to rebuild the Baltimore team with many of the techniques he learned in Houston.

The Yankees staggered through parts of the 2020 season and exited the playoffs earlier than most would have expected at the beginning of the season. With an AL East that is on the rise, and key decisions that did not pan out this season has Cashman left himself vulnerable as the Yankees key decision maker?