New York City, surprisingly, did not universally love Derek Jeter from the get-go. It was 1999, and Jeter entered a local Circuit City store looking for a videocassette recorder. A salesman was helping Jeter locate a VCR, and Jeter’s first three selections were out of stock.
According to a 1999 “Sports Illustrated” feature about Jeter, he settled for his fourth choice and was asked to follow the salesman to another register as the first one had malfunctioned.
Jeter joked, “Doesn’t anything work in this store? My credit card doesn’t work either.” The salesman replied, “Yeah, well, you suck anyway.” Jeter was taken aback and said, “I suck?” “Yeah, you suck,” the salesman said. “Griffey’s better.”
Jeter completed the purchase and moved on after regaining his composure. He never wavered and was built specifically for the bright lights of the “Big Apple.” It is no surprise he had so much success with the Yankees.
In 1999, he turned into the star of MLB. By 2014, when Jeter retired, he lived up to those expectations and exceeded them.
Derek Jeter: Prince of the City
Jeter was called up to the majors in 1995 and started 14 of 15 games at shortstop. He became the everyday shortstop in 1996 and won Rookie of the Year. Jeter quickly cemented himself as one of the Yankees’ best players, batting .314.
They beat the Atlanta Braves in the 1996 World Series and Jeter batted .361 in the postseason. He became the most beloved player in New York and was firmly in the spotlight.
He helped the Yankees win other World Series titles in 1998, 1999, 2000, and 2009, giving him five rings. Jeter didn’t succumb to the pressure of playing under the bright lights in a big city like New York City. He loved the pressure.
“You always hear players say, ‘I’d never play in New York,’” Jeter said in the “Sports Illustrated” article. “I don’t understand why you’d say that, unless you’re afraid to fail,”
Jeter learned from failure. He was never the best player in the league and never won the MVP award. Jeter showed up every day and played to the best of his ability, shining in the brightest moments. “Captain Clutch” batted .310 throughout his career in the postseason and .321 in the World Series.
He ranks first with 200 hits, 111 runs, 32 doubles, and 158 games played in postseason play. Jeter also holds the record for strikeouts in the postseason with 135. Jeter was never afraid of failure and failed often. The difference between him and many players who took the field in Yankee Stadium was the class and dignity that he showed despite failures.
One time Derek Jeter was in a terrible slump and Yogi Berra walked into the clubhouse. He sat down next to Jeter and was quiet for a few moments before saying:
“I think I know how to solve your problem: you should swing at strikes.” pic.twitter.com/FIW6W1Hor3— Jim Koenigsberger (@Jimfrombaseball) June 25, 2025
He earned the nickname “Mr. November” in Game 4 of the 2001 World Series. He hit a game-winning home run in the first World Series game in November after the tragic events of September 11 pushed the season back one week.
Jeter took the first pitch he saw over the Yankee Stadium right-field wall with two outs and nobody on base. Jeter tied the series and added to his legacy in pinstripes.
Jeter went on to amass 3,465 hits in his 20-year career. He had a lifetime average of .310 and hit 260 career home runs. He also led the American League in hits in two seasons, 1999 and 2012.
That’s a testament to his longevity and incredible talent throughout his career. Jeter became one of the greatest Yankees ever to don the pinstripes and did it all while being one of the best role models in the world of sports.