Brian Cashman is one of the most infamous names in baseball today. The New York Yankees General Manager has a tough relationship with the Yankee Nation. Although his tenure once was seen with pride, gradually things seem to have changed. But now that he has completed more than 37 years with the Bronx Bombers, he has become a mainstay of the Pinstripes. So when did he start and how did he become the GM of MLB’s most successful franchise?

Brian Cashman wasn’t always the GM of the Yankees, but he has been a Yank since his college days. His journey to the top is just as interesting as his time since reaching the summit. So what were the circumstances that led to the Yankees appointing him as their GM?

Brian Cashman’s journey to the top of the New York Yankees

Cashman was still in college when the Yankees came calling for him. George Steinbrenner was a friend of his father, John Cashman. Initially starting as an intern, Cashman gradually started working his way upward the Yankees management ladder. The Pinstripes gave him the position of Baseball Operations assistant after his graduation.

He worked in the minor leagues when a controversy gave him an unexpected push to the top. Steinbrenner was banned from baseball in 1990. This led to a complete reshuffle of the Yankees’ structure. He was called up to assist the daily operations of the team. By 1992, Cashman was the Assistant General Manager of the Bronx Bombers.

He remained in that position even as the team switched its GMs. This clearly showed signs that they were grooming him for bigger and better things. He saw his first World Series win in 1996. With such successes and the immense trust of the management, it was just a matter of when and not if he would become the New York Yankees manager.

The moment finally came in 1998. The Yankees appointed Cashman as their Vice-President and General Manager. He was now the third youngest GM in MLB history. Success soon followed him as the Yankees set up a dynasty by winning 3 consecutive world championships. He was suddenly the most loved figure in the franchise. But this perception did not stay for long.

Brian Cashman’s record since the dynasty years

Post-dynastic New York Yankees have been a shadow of their former selves. The Pinstripes did win a World Series in 2009, but everyone knew this was not a sustainable win. Cashman has seen his popularity wane with each passing year. The fan call for his removal keeps getting louder as the Yankees keep falling more and more behind their rivals.

Read more – Despite 2023 Disappointment, Brian Cashman Defends Yankees’ Operations as Title Drought Nears 15-Year Mark: “I’m Proud…”

The 4 time World Series-winning GM gets most of the blame due to his sometimes reckless decisions. His decision to not sign Bryce Harper or to give up on many other similar star players has turned him into a figure of ridicule among the Yankees Nation. Still, there is no denying that his impact on the Yankees is huge.

Now that he is entering another offseason as a GM, will he do something different this time? He could succeed in turning the fans on his side if he succeeds in luring stars like Juan Soto or Cody Bellinger into the Yankees fold.

Watch the story – Could Cody Bellinger’s Yankees Roots Influence His Free Agency Fate?