Derek Jeter: His Real Life On And Off The Field


Throughout his 20-year career with the New York Yankees, Derek Jeter was the ultimate symbol of excellence. He not only captivated a fanbase, but also the entire country, thanks to his countless high-profile relationships. Jeter epitomized success and celebrity in a way few others have.

King Of Baseball

Derek Jeter may be a retired athlete, but his baseball skills will live on for decades to come. With a career spanning over 20 years in the MLB, Jeter is a five-time World Series champion and a Yankees superstar. The Yankees drafted Jeter back in 1992 when Jeter was still in high school, and that was the year his life changed for good.

And Then A Hero Comes Along

With exceptional charm and good looks, Derek Jeter was bound to be a star beyond the baseball diamond. He caught the attention of a then-26-year-old singer named Mariah Carey as his career took off. She was married to music executive Tommy Mottola but found herself in the middle of a love triangle. Jeter and Carey met at a benefit event in 1996 and started what is considered Jeter’s first celebrity hook-up. After years of denial, she confessed that their romance lasted into 1998.


Universally Loved

Could Jeter’s spectacular 2000 season have been attributed to his dating life? Now that he was the crown prince of New York, beautiful women longed for him. This included Miss Universe. Jeter and 2000 Miss Universe Lara Dutta reportedly dated throughout the year. After winning Miss Universe, Dutta became a sensation in India. She launched a massive career in Bollywood. Whether we can accredit Jeter’s success to her or her success to him can be disputed. Undisputedly, they made for one beautiful couple.


A Parting Gift

Yankees fans should consider June 26, 1974, as their most significant holiday. Derek Sanderson Jeter was born to Dorothy and Sanderson Jeter on this day. The Jeters did everything they could to ensure that Derek and his younger sister Sharlee were model individuals. They made sure that they treated everyone with respect. As an adult, Jeter used the lessons from his parents when treating his ladies. During his single days, he reportedly sent girls home via limo with a gift basket of signed memorabilia.


Mr. Steal-Your-Girl

2001 was quite a successful season for Jeter and the Yanks, but his biggest steal of the season was not of a base but a girl. At the 2001 All-Star Game, Rodriguez introduced him to Joy Enriquez, a woman that he had been seeing. She was trying to make it as an actress, appearing in television series 7th Heaven,  and had contributed background vocals for Jeter’s ex Mariah Carey. Bad move, Alex. Jeter swooped in and began dating Enriquez for a brief fling.


Brothers At Arms

The late 1990s saw an influx in talented shortstops. In addition to Derek, Alex Rodriguez and Nomar Garciaparra became household names. Derek and Alex struck up a friendship after Rodriguez reached out about the pressures of being a high draft pick. It became the biggest bromance in baseball  but turned sour due to Rodriguez’s jealousy over Jeter’s admiration. After Rodriguez signed the biggest contract in sports history, he bad mouthed Derek in the press, and their relationship was never the same.


Yankees Focused Only

One of the biggest differences between Jeter and Rodriguez was how they approached the game. Alex loved everything about baseball, where Jeter loved everything about being a Yankee. A-Rod once went over to Jeter’s apartment and was baffled to find out that Jeter did not have the baseball package on his television. When he was asked about it, Jeter replied, “I don’t have that stuff.” Rodriguez could only ask, “What else do you do?” Derek only cared about his team’s games.

New York Yankees' Alex Rodriguez startles teammate Derek Jet

It Takes Two To Tango

Throughout his entire career, Derek Jeter proudly wore the number two on the back of his pinstripes. Interestingly enough, Jeter did not want number two and was hoping to get 13, the number his father wore in college. Legend has it that Yankees manager Buck Showalter told the equipment manager,”Give him two; he’s going to be special,” even though the number is not associated with anything specific. Coincidentally, frenemy Alex Rodriguez wore 13 when he and Jeter played together on the Yankees.

His Junior High School’s Prediction

As Jeter began working hard and improving as a baseball player, those around him began to notice. His classmates were especially keen to his abilities. They voted him as “most likely to play shortstop for the New York Yankees” in their junior high school yearbook. This was Jeter’s life goal, which he would eventually realize. Derek would become not only the best player in his school but one of the best in the country, winning numerous national awards in high school.


College Or The Pros?

Derek had a difficult decision to make following high school: would he accept a baseball scholarship to the University of Michigan (his favorite school), or would he turn pro with whichever team drafted him? The Yankees hoped to take Jeter with the sixth pick and prayed he would fall to them and choose the pros. Somehow, he fell to the Yankees and signed for $800,000. The five players chosen before him became career journeymen or minor leaguers.


Locked In The Bathroom

On draft day in 1992, Derek was quite nervous about where he would end up. After his name was not called in the first five picks, an anxious Jeter locked himself in the bathroom to be alone. As he tried to calm himself in the bathroom while awaiting any news about his future team, the phone rang and his mother shouted, “The Yankees are on the phone.” It did not matter where he received the call; he was going to the Yankees.

Realizing The Dream

Just a month shy of his 21st birthday, Derek Jeter made his major league debut. Due to injuries to infielders Tony Fernandez and Pat Kelly, Derek was called up to the majors on May 29, 1995. He was assigned jersey number two and would wear it throughout the rest of his career. In 13 games that season, he did not play well enough to make the postseason roster, but new manager Joe Torre announced that Jeter, the fourth-ranked prospect, would be the starting shortstop in 1996.


First Trip Down The Canyon Of Heroes

Every player hopes to have a rookie year like Derek Jeter. He hit a home run in the first game and carried that momentum throughout the season, winning Rookie of the Year unanimously. In the American League Championship Series (ALCS), Jeter notoriously hit a controversial game-winning home run with the help of young fan Jeffrey Maier. The Yankees would win that series and take home the World Series trophy against the Braves, their first since 1978.


Righting The Ship

Jeter and the Yankees had another good year in 1997 but lost in the American League Division Series (ALDS). They came back the next year looking for vengeance and unleashed a historic season on the way to a then-record 114 wins in the regular season. The Yankees plowed through the playoffs and took home another World Series trophy with Jeter leading the way. It was starting to look like Jeter, and the Yankees had a dynasty in the making.

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Dynasty Indeed

1996 and 1998 were only the beginning for Derek Jeter. Jeter and the Yankees would win two more World Series titles in 1999 and 2000. He continued to hit for average in the season and especially in the postseason. In 2000, Jeter became the first player to win All-Star Game MVP and World Series MVP in the same season. For his service, the Yankees gave him a fat contract worth $189 million over ten years, making him the second highest paid athlete in sports behind friend Alex Rodriguez.


Derek and Dubbya

In 2001, Jeter made sure to play up to his new contract. The tragic events of 9/11 would delay the postseason, but Jeter and the Yankees persevered into the World Series. Before Game 3 at Yankee Stadium, President George W. Bush threw out the ceremonial first. Before walking out to the mound, Jeter told President Bush, “Don’t bounce it our they’ll boo you.” With the world watching, President Bush tossed a perfect strike from the top of the pitcher’s mound.


Mr. November

If four World Series titles were not enough to make Jeter a legend, he solidified his position in the 2001 World Series. Due to the late start of the playoffs, game 4 took place on Halloween. With the game in extra innings, Jeter stepped to the plate. The clock struck midnight after the first pitch of the at-bat, becoming the first MLB game played in November. Derek hit a home run to win the game moments later, tying the series, and transforming him into “Mr. November.”


Fast and Furious

Although the Yankees would lose the series in seven games, Derek would head into 2002 as a winner. He began dating actress Jordana Brewster towards the beginning of the year. Brewster was acting in the CBS soap opera As The World Turns and was about to see her celebrity explode on the heels of the first Fast and the Furious film. She would reprise her role as Mia Toretto in four more installments. The relationship, however, lasted under a year, one of Jeter’s shortest.


Title Drought, Celebrity Surplus

Between 2001 and 2008 Jeter and his Yankees failed to win a World Series. Jeter’s personal life, however, was on the upswing. Following his relationship with Brewster, Jeter began a long-term relationship with Vanessa Minnillo. He started seeing the former Miss Teen USA in 2003. Minnillo’s career began to grow at that time as she was a host of Total Request Live (TRL) on MTV. He ended things in 2005 due to the very public nature of their relationship. She married Nick Lachey a year later.

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Dating The Dark Angel

While Derek and Vanessa were taking a break, Jeter began aggressively making dating moves with some of the biggest names in Hollywood. One of his finest flings was with Jessica Alba. She was still a year or two away from her roles in Fantastic Four and Sin City, but she was considered one of the most beautiful people in the business. Jeter dated Alba, ranked number one by Maxim magazine on their 2001 Hot 100 list, for a brief period in 2004.


Mr. November Meets The Black Widow

The 2004 season saw the Yankees complete a historic collapse in the playoffs to their arch-rivals, the Boston Red Sox. Jeter picked himself out of a rut with his various famous ladies. Although it was never confirmed, especially by the tight-lipped Jeter, rumors swirled that he was seeing Scarlett Johansson when he was not with Alba or Minnillo. She was 20 at the time and transitioning into adult roles, including 2003’s Lost in Translation. Scar-Jo would make a killing years later in Marvel films.


Bringing The Ship Back To The Bronx

An entire decade had almost eclipsed since the last time Jeter won a World Series ring. That changed in 2009. In their first season at the new Yankee Stadium, Jeter and his teammates captured the franchise’s 27th World Series victory. His fifth ring came next to his three oldest teammates: Jorge Posada, Andy Pettitte, and Mariano Rivera. The Core Four had been together since the beginning, coming up in the minors together and winning championships together.


Not Good Enough For MJ

Throughout Jeter’s career, he endorsed Nike products and had his own line of Jumpman shoes. The Jumpman himself, Michael Jordan, was not impressed with Jeter’s five championships because he has more. Jeter revealed in a 2012 interview that Jordan texts him “all the time” to boast about his six championship rings. Now that Jeter is retired, he has no chance to win a sixth ring and might have to endure a lifetime of abuse from Michael Jordan.


Baseball Twins

Baseball fans probably know the name Jason Kendall from his fifteen year career and three all star appearances. Kendall and Jeter have had bizarrely similar lives. For one, they share the same birthday – June 26, 1974. Jeter was chosen 17 picks before Kendall in the first round of the 1992 draft. Kendall likely won’t become a hall of famer like Jeter, but they share some similar statistics too. They both hit 16 minor league home runs, one career major league grand slam, and are top 15 in career hit-by-pitch.

A Victoria’s Secret Angel

Although he had been a bona fide star for a decade and he had dated a who’s who of Hollywood, somehow it took some time for him to find a Victoria’s Secret model. Some years before he got that fifth and final ring, Jeter had a quick fling with Adriana Lima.  It was a brief romance, but perhaps sparked her interest in athletes. She married former basketball player Marko Jaric in 2009. They later divorced in 2016.


America’s Next Top Jeter Lady

It took a decade to find a Victoria’s Secret model, but about a year after dating Lima, Jeter began another, if not the most famous, Victoria’s Secret Angel, Tyra Banks. Like many of Jeter’s famous flings, it only lasted for a short time. Tyra would be okay without Jeter and currently has a net worth around $90 million thanks to her show America’s Next Top Model. She was the creator of the show, served as executive producer, and also hosted the show.

America's Got Talent - Season 12

Before Timberlake

Before Jessica Biel became Mrs. Justin Timberlake, she was a rising actress and model. As her career began to explode, Biel and Jeter had a relationship towards the end of 2006 and into 2007. They were spotted on a handful of occasions together, including a vacation. Timberlake swooped in not long after as their courtship began in the winter of 2007. Biel and Timberlake have one son together and were married in 2012. Derek would have to wait yet again for his perfect lady.

Tiffany & Co. Gala - Arrivals

The Kid From Kalamazoo

Before he was a Yankee, Derek Jeter was just a kid from Kalamazoo, Michigan. Since he had family still in New Jersey where he was born, he spent many summers there going to Yankees games with his grandparents. Although Detroit was not far too far away, Jeter became a huge Yankees fan thanks to the time spent with his grandparents. Hall of Famer Dave Winfield became his favorite player and sparked his interest in playing professional baseball.


Clear Eyes, Full Heart

In 2008, Jeter started his steamiest relationship to date. He began seeing Friday Night Lights star Minka Kelly, and it seemed to correspond with his success. The Yankees won the World Series in 2009 and Minka joined Derek on a float during the championship parade. When Jeter hit a home run for his 3,000, the two were still together. Not long after, Derek ended the relationship. It is rumored, that like his past relationships, Derek did not like how public their relationship had become.

2009 World Series Champions the New York Yankees ride down Broadway. The Canyon Of Heros for a ticker tape parade.

A Fitting End In Pinstripes

Before the 2014 season, Derek announced that he would retire at the end of the season. While the season itself was uneventful as the Yankees failed to make the playoffs, teams around the league paid their respects to The Captain by showering him with love and gifts. Even the Red Sox faithful gave him a standing ovation. In his last at-bat at Yankee Stadium, Jeter hit one of his patented opposite-field singles to win the game, a perfect ending to a great career.


An Underwear Predicament

Since retirement, Jeter found himself in the middle of a legal battle of an interesting product: underwear. RevolutionWear, a company which works with underwear brand Frigo, owes Jeter $90,000 in unpaid legal fees. He sued them in March 2016 and has since asked the judge to impose a $100 fine per each day the payment is late. Initially, the company tried to sue him for $26 million for backing out of a deal. Instead, they found themselves on the losing end.

Do It For The Kids

When he could no longer play baseball and show up for his fans, Jeter decided to enter into a venture aimed toward his youngest fans. In 2013, Jeter launched Jeter Publishing (an imprint of Simon and Schuster). Much of Jeter Publishing’s projects target children’s books. One book, Night at the Stadium, is like a combination of Field of Dreams and A Night at the Museum. Jeter has final say on all titles that the company signs.

Finding The One

It seemed as if Derek Jeter would remain New York’s most eligible bachelor forever. That is, until he met Hannah Davis. The model is 16 years younger than Derek, but they began dating in 2012. After a handful of breakups, the couple finally decided to solidify things. Derek proposed in 2015, and they married in 2016. When she met him, she barely knew who he was and thought that he was a pitcher. Now she bares the name of one of the greatest winners ever.

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Introducing Baby Bella

While ladies everywhere cried over the fact that Derek Jeter was off the market, Derek and Hannah Jeter made another shocking announcement – Hannah was pregnant, and they were expecting a daughter. Baseball fans will still have to wait for another Jeter to don the pinstripes. On August 17, 2017, they welcomed Bella Raine Jeter into their family. After years of testing the water, Derek finally had the family that he deserved and could cherish into his retirement.


What’s Next?

Now that he has retired from baseball and has a wife and child to take care of, what’s next for Derek Jeter? In 2014, he started The Players’ Tribune, a website which allows athletes to write first-person stories. His newest endeavor has him back in baseball, this time as an owner. Jeter (and his $185 million net worth) joined a group which purchased the Miami Marlins. He owns 20% and is the team’s CEO. Although not with the Yankees, it’s good to have him back in the MLB.

Derek Jeter

King Of New York And The Ladies

The New York City Streets have stories for days about Derek Jeter. Jeter ruled the Big Apple as a ballplayer, but it’s his history as a Don Juan that made him a legend in the tabloids.