The black and white video begins with the 40-year-old future Hall of Famer asking his driver to pull over just a few blocks from Yankee Stadium in the Bronx.
Along his walk to the ballpark, Jeter greets kids at a local park with Frank Sinatra's "My Way" playing in the background.
Jeter stops by a well-known bar called Stan's Sports Bar, located in the shadows of Yankee Stadium. Mike Rendino, the general manager at Stan's, tells the Yankee captain he's been waiting for Jeter to walk into the bar since 1998, the year he started working there.
Jeter responds, "You never invited me," to a chorus of laughs from patrons.
In an interview with ABC News, Rendino said he had a "heads up" that Jeter would walk into the bar, but "couldn't tell anyone."
"The few [employees] I could tell, I was emotional telling them because I was so excited," Rendino said.
Yankee fans in the bar at the time were "shocked" and some didn't even know how to react, Rendino recalled.
Jeter was supposed to spend only a few minutes at Stan's, but ended up hanging out for about 15 minutes to speak with customers. At one point, Rendino said, the All-Star shortstop "requested to go behind the bar."
"Fans feel like they are part of his goodbye," he said.
Molly Carter, senior director of marketing at Gatorade, was with Jeter in July on a 97-degree day when the commercial was filmed before a Yankees home game. Carter knew the commercial was a success once Jeter and the small film crew arrived at Stan's.
"That's when we knew we came up with something good. Derek Jeter was so natural and genuine," Carter told ABC News.
"Everyone in the commercial was hired by Gatorade, but they had no idea they were in a Derek Jeter commercial," Carter added, saying that nothing was scripted as the Yankee legend strolled through the Bronx. Fans were never told it was a commercial involving Jeter, let alone he would make an appearance.
Carter said the entire commercial was filmed in almost two hours. Any other commercial of that magnitude should've been filmed in at least eight hours, Carter said, pointing out that "time was tight."
The area near Yankee Stadium was shut down in order to make sure Jeter was secured, she said.
Carter said her first meeting with Jeter about the possibility of doing a commercial happened in March after he announced his retirement in a letter to fans on Facebook.
"The inspiration [for the commercial] came from the retirement letter, thanking the people of New York," Carter said.
It was also in that meeting Carter asked Jeter about what song to use for the spot. Jeter chose Sinatra's "My Way" because it epitomized his career, Carter said.
As Sinatra hits the crescendo of the song at the conclusion of the commercial, Jeter is seen standing in Yankee Stadium's Monument Park, where other pinstripe legends have plaques and retired numbers -- a place Jeter will one day be honored.
The Gatorade tribute follows Nike's "Respect" ad earlier this year. With only a few games left in Jeter's legendary career, you can expect more tributes and tears to come.