He has reportedly dated Jessica Alba, Jessica Biel, Jordanna Brewster, Mariah Carey, Minka Kelly, Adriana Lima, and former Miss Universe Lara Dutta, to name a few, and legend has it he gave gift baskets of autographed memorabilia to one night stands.
And yet, Derek Jeter was once described by former Red Sox ace Curt Schilling as someone who has "always been above the fray.” As a GQ article by Seth Mnookin about his “Swinging Years” noted in 2011, “he's Tiger without the car crash, Kobe without the rape trial, Brady without the jilted pregnant girlfriend, A-Rod without the...well, everything.”
To some extent, the public has never gotten to meet the real Derek Jeter. “My number one priority was on the field,” he said of keeping his private life private. “I've had fun. It's not like I've never gone out; I've done a lot of things. But I've always kept sight of my number one priority.”
In retirement however, Jeter no longer has to prioritize his persona as an athlete, and we have, perhaps, seen cracks in the facade as he explores new roles as family man, entrepreneur, and giving voice to athletes to speak directly to their fans.
With that in mind… here are 15 Things You Didn't Know About Derek Jeter Since His Retirement
15 Still “Captain” Of The Yankees
In the two years since his retirement from baseball in 2014, Jeter has made surprise appearances at the New York Yankees’ annual “Captains Camp.” The club began the program in his final year as a player, pairing their most promising young players with an array of big name instructors in their training facility in Tampa, FL, mentoring them to not just be better athletes but better people. This year’s camp started January 18 and ends February 24 and Yankee legends such as Andy Pettitte, Tino Martinez, and Alfonso Soriano are expected along with current players and coaches, including of course, Alex Rodriguez.
“As the New York Yankees, we set the standard for how to prepare and compete as a professional,” Vice President of Player Development Gary Denbo said. “Captains Camp is about developing good men that will become the leaders of our future championship teams.” Its certainly hard to think of a better example of that goal than five time champion Derek Jeter, the only captain the team has had in the last twenty years.
14 Engaged In A Lawsuit Involving Underwear
A company called RevolutionWear, a marketer working with the luxury underwear brand Frigo, reportedly owes Derek Jeter $90,000 in unpaid legal fees after he sued them in March of 2016. He has also recently asked a judge to force them to give him $1000 a day for each day they’re late in paying up. The company had reportedly wanted $26 million from Jeter for allegedly backing out of a deal that gave them permission to use his “name or likeness to promote the products,” but has ended up owing him money instead.
Jeter has not walked away from the proceedings unscratched however, as there have been allegations against him alleging he demanded that the company not market to the gay community and that he was angry when 50 Cent, a Frigo investor, was selected to be the brand ambassador because he didn’t want the brand to be “too urban.” Jeter responded that he was disgusted by the allegations and that they were “categorically false.”
13 Building A Wall
Derek Jeter’s nine-bedroom Tampa mansion has become a huge tourist transaction since he finished construction in 2011, so the city recently granted him special permission to expand the height of his gate to keep paparazzi from stealing pics. While the local law limits gates to be built at a maximum of four feet in height and requires that one can see through them, Jeter will be installing an eight-foot-high gate with sheet metal backing.
People hang out there," Jeter representative Stephen Michelini said. "They're looking for snapshots. They come at all times of the day and night. The neighbors have become the enforcers here, and frankly, they're getting tired of it.” Tampa mayor Bob Buckhorn has a different take on who is to blame for the former Yankee needing to block the outside view. “I’m sure there are a number of Christmas cards in New York with people standing in front of Jeter’s house with their family,” he said.
12 Got Married
There’s another reason Derek Jeter now has to want to keep people from peeking onto his property, In July of 2016, Jeter, then 42, married 26-year-old Sports Illustrated swimsuit model Hannah Davis.
He had proposed to his bride in October on the eve of their third anniversary, with a diamond estimated to be between four and six carats, after asking her parents “for permission” to marry her months earlier. Davis, who is originally from the Virgin Islands, took a very “chill” approach to planning the big day. “ I just want it to be a fun day, not all the fuss,” she said. “I don’t want to go overboard — it’s not about the place settings. I won’t get stressed out about that, ’cause I could just care less.” She did get to wear a custom-made Vera Wang gown, but otherwise it was a small and intimate ceremony with only close friends and family held in Napa, CA. Of former teammates, only Andruw Jones, Tino Martinez, and Jorge Posada made the cut to be amongst the audience.
11 Co-Founded Popular Website
Jeter co-founded The Players’ Tribune, a website dedicated to content created by the athletes themselves, in 2014. The company recently announced it has more than tripled its start-up financing, growing from $18 million to $58 million. “We’re basically a pretty small company,” Jeter told Fortune. “But we’ve been able to establish our brand and grow, and this gives us a chance to help us scale further.”
What began with just a few dozen contributors writing about their personal experiences in sports now has over 1,200 athletes creating content consumed by over a million views per month. Most famously, the site crashed after Kobe Bryant used it to announce his retirement in 2015 because of the amount of traffic it suddenly took on. Jeter was inspired to create the website by just such a direct connection it could offer between players and their supporters. “I do think fans deserve more than ‘No comments’ or ‘I don’t knows,’” he wrote in a post.
10 Standing Up To Bullying
“We know what it’s like to be bullied or trolled,” Jeter said of the many sports stars he has recruited to participate in a campaign called “STAND UP” on his popular website, The Players’ Tribune. The first step is a viral video recently released that stars NBA center Karl-Anthony Towns, NFL linebacker Von Miller, NASCAR’s first female driver Danica Patrick, Olympic legend Michael Phelps, and Jeter himself each reading some of the hateful comments they have received on social media.
“Everyone’s anonymous,” Jeter said of the current climate’s failure to combat what his website’s press release called “divisive rhetoric.” He continued “there’s no connection there. People that don’t know you, never know you and probably never will know you that are saying hateful things.” Other athletes who will be releasing videos through his website in coming weeks range from Joel Embiid to Andrew McCutchen to Abby Wambach and many more.
9 Another Start-Up Company
Within a week of the influx of capital to The Players’ Tribune, Whistle Sports, another startup Derek Jeter co-founded (along with, prominently, Peyton Manning), a viral/social sports video media company, raised $25.5 million.
Founder and CEO John West will look to build upon the corporation’s early success with the new cash to spend. "Backed by this new investment, we are excited about building on this success and continuing to grow in 2017 and beyond," West said. "In particular, we look forward to further developing our analytics practice to provide brands with the detailed insights they need to better understand and engage with millennial sports fans.”
In other words, expect more videos that appeal directly to you coming your way on YouTube, Facebook, and more in the coming months.
8 The Jeters Have A 100 Pound Dog
There are reports that Jeter is “definitely ready to be a dad” but, for now, he and Hannah Jeter are parenting a two-year-old Italian mastiff named Kane, a 2014 Christmas present from her to him, on their thirty thousand square foot mansion in Tampa, FL. To hear a neighbor describe it though, Kane has not always been the easiest canine to manage. “When he first got it, it was a cute little puppy, but it became controversial on the block,” said a neighbor. “All of the dogs are afraid of him. He was outside barking all of the time. It wasn’t a normal bark. It was a bark you could hear blocks away.”
Jeter doesn’t hesitate to agree. He wrote on his Players’ Tribune website that he was “previously scared of dogs” and that “discipline is proving difficult” with the 100-plus-pound Kane.
7 Jeter Publishing
Launched in 2013 as a Simon & Schuster imprint, Jeter Publishing has released baseball themed literature like “Night at the Stadium,” a children’s book described in its press kit as a combination of “Field of Dreams,” "Alice in Wonderland,” and "A Night at the Museum.” Beyond baseball, “Muhammad Ali Unfiltered,” a tribute to the legendary boxer who passed away in June of 2016, was published just a few months ago. They also offer non-sports specific writing, and apparently had pursued Tracy Morgan’s memoir but ultimately did not land the project.
In fact, Jeter himself has final approval over which titles are signed. “He talked about being very involved in the acquisitions process,” says agent Jennifer Keene. “[He and his partners] stressed that Derek’s name is on the imprint doesn’t just mean [authors] are signing up — and they aren’t just throwing money at people. There is a sound business sense there.”
6 Making Use Of All Of Those Retirement Gifts
Amongst the goodbye presents Derek Jeter collected during his final stops at various stadiums across the United States and Canada were a 10-day trip to Tuscany, Italy, received from his Yankees, a vacation to a Napa Valley resort from the Oakland Athletics, and a getaway in the Canadian Rockies, from the Toronto Blue Jays of course. And it turns out, he’s actually used them. “He’s been a globe-trotter,” one baseball source said. “A lot of teams offered trips, and he made good on all of them.”
He also traveled to Cuba in March of 2016, coinciding with Barack Obama making the first visit to the country by a U.S. president in nearly ninety years, to watch his now hometeam Tampa Bay Rays play against the host’s National Team.
5 To Boston Fans, He’s Still Derek Jeter
After years of torment, the Red Sox fan base maintains a love/hate relationship with Jeter, even in retirement. “[When they come up to me,] they always say, ‘I’m sorry, but I’m a Boston fan,’” Jeter joked on Late Night With Seth Meyers. “I don’t care if you’re a Boston fan. We’re not at the stadium. Just don’t yell at me in restaurants.”
Of course, with Hannah in his life, he is no longer alone with being recognized in public. A man complemented his wife’s beauty this past New Year’s Eve while the couple was dining at Bern’s Steak House in Tampa. Jeter responded graciously and even picked up the check for the man’s dinner, agreeing with him that the model on his arm was the “most beautiful in the world.”
4 Last To Wear #2 In A Yankees Uniform
On May 14 of this season, the New York Yankees will officially retire the #2 worn by Derek Jeter and add a plaque to their Monument Park in his honor. It is perhaps no coincidence they are doing so on Mother’s Day. Dorothy Jeter was a well recognized presence at Yankees games along with her husband for much of her son’s twenty years will the club.
With the retirement of Jeter’s number not only will there never again be a #2 on the back of any Yankee player, but there will never be another single digit as he joins Billy Martin (#1), Babe Ruth (#3), Lou Gehrig (#4), Joe DiMaggio (#5), Joe Torre (#6), Mickey Mantle (#7), Yogi Berra/Bill Dickey (#8), and Roger Maris (#9). Not bad company to keep.
3 Mulling A Return To The Majors… As An Owner
"The ultimate goal, the ultimate aspiration, is on the ownership side. But not right now,” Derek Jeter said after walking the red carpet at the annual gala for former manager Joe Torre’s Safe at Home Foundation this past November "I needed to get away from the game, so I got away from the game for a while. I didn't watch. This year, I saw a few more games than in the past.”
He added that he is “trying to learn” about owning a team in the future but “there’s no news to be broken today.” He said he would think about it if the Yankees asked him to be more involved, but there are also rumors of his interest in the Tampa Bay Rays, who play of course just miles from his house.
2 New Sport To Conquer
Only two years after his retirement from baseball, Derek Jeter made a debut in a new sport, one familiar to other retirees across the country… golf. “You’ve got to find something that sort of quenches that competitive thirst after you retire,” he noted. He teed up this past December for the Hero World Challenge at the Albany Golf and Beach Resort Club in Nassau, Bahamas, which long time friend Tiger Woods was hosting. Jeter has had a standing invitation for some time to participate in any tournament Woods hosts, but didn’t think his game was in good enough shape to reveal to the public. Even when he hosted his own charity golf tournament, he limited his playing to just one shot. “I embarrassed myself a lot through my career, but never intentionally,” he said. “So I stayed away from it.”
Jeter has lowered his handicap to a 10 since his retirement, but still can relate to the challenges of hitting on the greens. “It’s probably the most frustrating thing I’ve done, because the ball’s not moving, right?”, he joked. “I can hit it, but it just doesn’t go where I want it to go. So I’ve gotten addicted to trying to improve.”
1 Still Parties With The Best Of Them
Renowned for his partying during his playing days, Jeter has been otherwise occupied with his many business ventures, traveling, and spending time with his new wife since retirement. But in October of 2016, he threw a massive party to raise funds for his Take 2 Foundation at Cipriani in New York City. Jorge Posada and current Yankees CC Sabathia and Dellin Betances were there, but other celebrities included Tiki Barber, Hoda Kotb, Andrew McCutchen, soccer star Ronaldinho, Dave Winfield. and Ne-Yo, who performed.
And, with a former Sports Illustrated Swimsuit Cover Girl for a wife, Jeter can still draw headlines like “Spent His Sunday Night Partying With 30 Model Types,” as he did in 2014.
Seems like he still has it. It’s still pretty good to be Derek Jeter, even without the #2 on his back.