Despite Winning 5 Championships, Derek Jeter Details How “Every Season With The Yankees” Led To A Sports Heartbreak

The New York Yankees define eras in history. The franchise can boast a number of iconic names through the decades of its existence, including Derek Jeter. Like any team in sports history, the Pinstriped club went through a rollercoaster of ups and downs. But by the time Captain Clutch signed on, the deed was done. The Yankees had a huge name and following in baseball. Unfortunately, it didn’t last too long.

When looking at the players that made the franchise, Jeter’s time with the team represents a powerful age. Immediately after his arrival, the Yankees surged to the top, almost suddenly. But what is sometimes forgotten is the dark ages that preceded the arrival of the kid from Kalamazoo, and what an impact they had on him.

The New York Yankees Were Derek Jeter’s First Sports Heartbreak

Growing up in Michigan, all Derek Jeter had ever wanted in life was to play shortstop for The New York Yankees. On May 29, 1995, he did it, slowly re-establishing the dominance of a dynasty that had been asleep for too long. The 70s and the 80s were the most depressing few decades for a Bronx lover, and Jeter was nothing if not a die-hard fan.

In a recent interview called ‘My Firsts’ with The Players’ Tribune, the Hall of Famer sits at a desk, signing booklets. When the interviewer asks him about his first sports heartbreak, he has an easy answer. “Pretty much every season with the Yankees when I was growing up,” laughs the retired ballplayer.

So he decided to change things up when The Bronx Bombers signed him, winning four World Series championships in five years, although his total tallies at five rings. The ‘Derek Jeter Era’ is still one of the most fearsome ages in American League history, something today’s Yankees can only dream of. Nevertheless, the Captain’s twenty seasons in the league will always be one of the greatest ages in the franchise’s history.

Dave Winfield Was Captain Clutch’s Inspiration

Everyone has a hero, a role model they look up to and want to emulate in their own lives. Derek Jeter had Dave Winfield, a man who stood the test of time even in the toughest Yankees years. When the ex-shortstop met the retired right fielder, an everlasting friendship was forged.

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Winfield was the first jersey that Jeter bought for himself, as he explains in the same interview. “You know sometimes they say don’t meet your heroes but Dave always treated me great since I was young. And we’re still friends today,” the former slugger tells the camera.

Well, just like someone inspired Jeter, The Captain has serve as an inspiration for today’s Yankees.

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