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via Getty

via Getty

In September 2014, after spending 20 years in Pinstripes, the sun finally set on Derek Jeter’s storied, widely loved, respected, and adored MLB career in the city that never sleeps. While this emotion was particularly augmented within the Big Apple, American’s including various Bostonians, gathered all across the country to celebrate the distinguished career of a leader who carried the heart of the New York Yankees. And the support of every New Yorker. After making his debut in 1995, Derek Jeter was about to hang his Yankee boots in September 2014.

Shortly before the shortstop reached the Bronx, before his final walk to the park decked in Pinstripes, the Yankees captain decided to stroll the city he called home one last time; with Frank Sinatra’s classic hit “My Way” serving as the soundtrack. It was a poignant moment, captured on film by Gatorade, as the great shortstop bid farewell to the place that had seen him rise to greatness.

Derek Jeter took a final bow in New York, through Gatorade

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The commercial begins with the Yankees legend getting off his car, by lauding, “You know what, I’ll walk from here.” Ensuing this, the 2009 Roberto Clemente Winner strolled the streets of New York, with every New Yorker recognizing him, and standing in disbelief at being faced by their loved Yankees captain.

Very accurately backed by Sinatra’s My Way, the entire city exploded at the sight of the Yankees captain standing right outside Yankee Stadium. Before he decked the number two for one last time. Seconded by rival team’s boston.com, “It’s almost enough to make a Red Sox fan sentimental about Derek Jeter’s impending retirement, and we probably don’t need the almost.”

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As Jeter walked through the streets, he knew that he had given it his all, leaving nothing on the field, and leaving a lasting legacy that would be remembered for years to come.

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Following his retirement, the Yankees’ front office retired his jersey number two in 2017, followed by a plaque in Monument Park. In 2020, with a record 99.75 majority in the Hall of Fame ballot, Derek Jeter made his way to the great Hall of Fame.

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Which is your most remembered memory from Derek Jeter’s 20-year career with the New York Yankees? Let us know your thoughts in the comments below!