'What's a Scarlet Letter?' The Improbable Reinvention of A-Rod

Yes, Alex Rodriguez is engaged to Jennifer Lopez. Yes, they spend their days frolicking across the celebrity landscape, from the Oscars to the Met Gala. But here’s the really crazy part: He’s popular.

Sports Illustrated’s annual “Where Are They Now?” issue catches up with the stars and prominent figures from yesteryear—past features have included Sammy Sosa, Brett Favre, Dennis Rodman, Tony Hawk and Don King. The 2019 issue features an inside look into the new life of Alex Rodriguez, Yao Ming’s mission for Chinese basketball and more.​

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As much of the world focused on Lady Gaga and Bradley Cooper making love via duet onstage at the Oscars on Feb. 24, I kept squinting at the man who occupied the seat directly behind the one that her ladyship had just vacated. Like everyone who keeps an eye on baseball, I had tracked his climb from the depths, but I still couldn’t quite believe that he’d ascended to the center of the second row—in frame for nearly 30 million viewers—for perhaps the year’s most indelible pop cultural moment. But his pearlescent, Cheshire Cat smile, matched by the white of his dinner jacket, was unmistakable. What the hell, I thought, is A-Rod doing there?

It turns out that 43-year-old Alex Rodriguez was at that moment similarly incredulous. How the f--- did I get here?, he asked himself, f-bomb and all; he uses it a lot, as you’ll see. That had been what he was thinking as his girlfriend, Jennifer Lopez, reassured a shaking Cooper during the commercial break before Cooper’s performance. (“When you hear the song, and you hear the people’s reaction, jump on that wave and go with it,” Lopez told the experienced actor but amateur singer.) And it’s what Rodriguez wondered as he watched Cooper and Gaga nail their showstopper from A Star Is Born. It’s a question A-Rod asks himself all the time, and it’s not a logistical one.

Five years ago he thought he was ruined, and so did every-body else. “This is f------ bulls---!” he had screamed before storming out of Major League Baseball’s offices and into the barricaded media circus awaiting on Park Avenue, thereby ending his participation in arbitration hearings that would result in his being banned for the entire 2014 season. It was the sport’s longest-ever suspension for performance-enhancing drugs, its extent justified not just by the strong evidence against Rodriguez but also by his determined efforts to impede the league’s investigation. It was, it seemed, the death knell for A-Rod’s reputation, if not his public life.

This spring, though, he visited MLB’s offices under happier circumstances: The league had invited him to consult on how to engage younger fans, and to discuss his leading role in promoting the Yankees–Red Sox series in London.

“It was surreal,” Rodriguez says. “Same building, same revolving doors, same security guards, but a completely different situation.” The familiar question flashed across his mind.

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The answer begins around Opening Day of 2014, when he forced himself to turn on the TV and watch the Yankees’ first game without him. “I was sitting there crying,” he says. “It was torture. It was like being a masochist. I was broken, dead, tapping out, thinking crazy things.” He had already decided to drop his lawsuits against baseball, to accept his penalty, but he had no idea what the result of that would be.

Not long after, he secretly met with Rob Manfred—then the league’s chief operating officer under commissioner Bud Selig, and the man who had led the takedown of baseball’s biggest star—this time entering and exiting through a back door. “Once you serve your suspension, you become just another player,” Manfred told him. “There will be no scarlet letter.”

“Great,” Rodriguez said. “What’s a scarlet letter?” The explanation, says Rodriguez, “gave me the confidence that once I serve my suspension, I’m free. I found that to be incredibly liberating.”

Since then, says Manfred, “I think that he has accomplished more than I would have guessed possible.”

Rodriguez had already done that in 2015, when—after issuing a handwritten apology to the fans, the Yankees, the league and the players’ association that was heartfelt yet notably unspecific about his misdeeds—he returned to the field. That season, as a 39-year-old DH with two surgically repaired hips, he slugged 33 homers and drove in 86 runs, satisfying those easily swayed by athletic exploits in the face of dismaying off-field behavior.

The next year didn’t go nearly as well—he batted .200, with little power—and in August the Yankees retired him with a ceremony at their home ballpark, four home runs short of 700, the fourth highest total ever. It felt like a tidy ending to a messy yet unprecedentedly lucrative career, and a final farewell.

It was not. Just three years later Rodriguez is everywhere. He is not just a respected fixture on Fox’s postseason studio show, but also in the booth each Sunday night for ESPN’s nationally televised game, greeted with hugs in every clubhouse he visits, the Red Sox’ included. “He’s the defining voice for baseball, in a weird way,” says Bardia Shah-Rais, Fox Sports’ coordinating producer. “In a good way.” 

He is the constantly besuited CEO of A-Rod Corp, his investment company, which he says has hundreds of millions of dollars in assets and several dozen employees. That gives him the business bona fides to host a popular Barstool Sports podcast, The Corp, along with Dan (Big Cat) Katz. Rodriguez draws the entrepreneurial guests: Kobe Bryant, Mike Francesa, Gary Vaynerchuk. Barstool pulls in the young demographic. The company is often criticized for misogyny, but Rodriguez, so far, has avoided the flak others have received for associating with the brand. “What other guy can work for Fox, ESPN and Barstool?” asks Katz, who in 2017 had an ESPN show canceled after one episode when the network deemed Barstool too toxic. “That’s almost incredible.” 

Rodriguez is also a shark on Shark Tank, a host on CNBC, a frequent guest on The Tonight Show Starring Jimmy Fallon and the squire to J.Lo for not just the Oscars but also the Grammys, the Met Gala and pretty much every other celebrity mega-event there is. All of which he assiduously documents on Twitter, Instagram and YouTube, followed by a total of more than four million people.

He is, in other words, a celebrity himself, to a greater degree than any baseball player in decades, let alone one who was recently disgraced. 

Robert Beck

“It’s really the comeback story of all comeback stories,” says Yankees owner Hal Steinbrenner, to whom Rodriguez is a special adviser. Billy Corben, the director of the recent documentary Screwball, which digs into the Biogenesis scandal that ensnared Rodriguez, has put it in stronger terms: “We haven’t seen a resurrection like this since Jesus Christ.”

So: How the f--- did he get here? “I fell from the Empire State Building,” Rodriguez says. “Nobody pushed me. I f‑‑‑‑‑‑ jumped. No parachute. I have no one to blame for myself. But what’s changed is, I got my ass humbled. I paid a deep penalty. I’ve learned lessons. And I’m different.” 

Most people who experienced all that and still emerged with career earnings of some $450 million would probably spend their remaining years holding putters and tillers. “I wish I actually liked to, like, play more golf, or go boating,” Rodriguez says. But he’s always been existentially driven to be more than he already is—which, when you think about it, accounts for both his baseball successes and transgressions. In his post-baseball life, that has meant two things: attempting to change, yes, but also communicating to the world that he has done so, a task that can require even more work than change itself. 

Luxury brands matter a lot to Rodriguez, and his world brims with them: Mercedes, Rolls-Royce, Hermès, Balmain, Tom Ford, the Yankees. He owns his own brandmark, which doubles as his company’s logo. It’s a Jordan-like silhouette of Rodriguez in full backswing, with a contrail following his bat. During the seven days I spent with him over the course of this spring, I saw his logo everywhere—on his sweatshirts, his sweatpants, his coffee mugs, the floor of his indoor basketball court, the lumbar pillows and the tail of his Gulfstream jet—and though I can’t recall ever seeing it anywhere else, I’m sure people who are not him buy and use some of this stuff too.

In fact, Rodriguez transformed from mortal into luxury brand himself in 1996, the first time Mariners broadcaster Dave Niehaus referred to him by the nickname that would stick: A-Rod. Back then, A-Rod meant Golden Boy, the handsome, strapping, bilingual star who was nearly the AL MVP at 20 and promised to break every record. Then, long before his steroids suspension, his brand broke bad.

He became, in general chronological order, the overpaid Rangers slugger whose team couldn’t win, the glove slapper, the shirtless sunbather, the World Series hijacker, Madonna’s boy toy, the mirror kisser, the owner of paintings depicting himself as a centaur, the admitted if then unpunished PED user, the eater of popcorn from Cameron Diaz’s hand. 

Worst of all, Rodriguez seemed phony. Which he was, as he now understands. “I had it backwards,” he says. “I tried to say the right things, to be manipulative, instead of doing the right things.” He calls that version of himself the Robot. The Robot didn’t think he owed anyone anything to begin with, least of all the media. “For so long, I took the approach that it doesn’t matter what they write; I’m just going to go out and be the best baseball player I can be,” he says. “I didn’t realize that it actually does matter.” (For the record, as far as the centaur paintings: “Never true.”)

A couple of years after he became A-Rod but before everything went south, he was asked, on camera, to describe his dream date. “Jennifer Lopez,” he said, his hat insouciantly backward. “Hopefully you can find me a date with her.” 

Two decades later, the 49-year-old Lopez perches on a sofa in the living room of Rodriguez’s pristine, modernist house on 1 1⁄2 walled acres in Coral Gables, Fla., one of six or so residences they own between them, though their real estate holdings often change. She’s wearing a gleaming diamond on her left ring finger, a bauble on which Rodriguez reportedly spent $1.8 million, presenting it to her on a Bahamian beach in March. She sits in front of the centerpiece of his extensive art collection, an Andy Warhol portrait of Jean-Michel Basquiat, which A-Rod particularly prizes because they are his two favorite artists. She talks about how she and Rodriguez met.

Their first encounter was actually in a tunnel at Shea Stadium in 2005, when both say they felt a frisson that perhaps only a pair of incredibly good-looking and famous people, with similar backgrounds and similarly formulated nicknames, can experience. “We shook hands, and it was this weird electricity for, like, three seconds,” she says. “Three to five seconds of looking at somebody right in their eyes, and getting stuck.” Alas, both were married, she to the singer Marc Anthony and he to the former Cynthia Scurtis.

A lot happened after that—a second daughter for him and twins for her, two divorces for her and one for him, hundreds of millions of dollars in earnings, mild career turbulence for her and what had seemed like permanent disgrace for him—until they saw each other again at the Beverly Hills Hotel early in 2017, five months after his retirement. Or, rather, until she saw him. He was so engrossed in conversations with Michael Strahan and Jamie Foxx that he didn’t notice her until she tapped him on the shoulder.

A few nights later they met for dinner at a secluded back table at the Hotel Bel-Air. Rodriguez, in Lopez’s telling, launched into a long, winding, often name-dropping monologue: He wanted to get into producing; he knew Guy Oseary, the powerful talent manager; he didn’t think he’d get married again until he was 45; he’d never dated a Latina; he’d never really been in love. “I realized afterwards he was a little nervous, saying all this stuff you would never say on a first date,” Lopez says. Then he excused himself to go to the bathroom, and shortly thereafter her phone vibrated. YOU LOOK SEXY AS F---, he’d texted her.

“Actually, it was good game, because it was very unexpected and it was super flattering,” she says. “I wasn’t dressed very sexy.”

After that, he sent her a gift: a copy of the bestselling book Grit, by Angela Duckworth, which is subtitled, “The power of passion and perseverance.” He told her, “This just reminds me of you.” 

The two quickly realized that not only did they have much in common but that they complemented each other too; theirs could be both a romantic and a commercial merger. “I’ve been in the public eye, I’ve navigated the media in a certain way, I’m creative and artistic and have all these skill sets,” she says. “He’s a business-minded guy who knows math and numbers and money and equity and all that stuff—like, EBITDA, right? What I was missing, he kind of had. And what he was missing, I had.” He taught her that instead of licensing her image to other companies, she should have ownership stakes in the businesses themselves. “She had sold, like, two billion in perfumes—and she’d made a few bucks,” Rodriguez says. “That’s not good.”

Less than a month into their courtship Rodriguez sent Lopez a video of a press conference he’d just conducted upon his arrival at Yankees spring training, where he was serving as a special instructor. He had been asked if he missed playing baseball and replied, flatly, that he didn’t.

“How was it?” he asked.

“It was good,” she said.

“Tell me.”

“You could have smiled, once,” she said. “You’re silly, you’re funny; I know that now. And why did you say you’re fine without baseball? You love baseball. You miss baseball. It’s O.K. to let people know that.”

The Robot had returned. “The key to being in the public eye is being your best self,” says Lopez. “It’s not being fake. It’s being you. But the best version of you.”

Eric Espada/Getty Images

Others had tried to help Rodriguez realize this before—like Ron Berkowitz, the ace crisis publicist who has advised him since 2013 and whose client list includes Robert Kraft and Meek Mill. Rodriguez had made something of a breakthrough on Fox during the 2016 playoffs, when he emerged as the natty, insightful, often goofy counterpart to his rumpled deskmate Pete Rose. But Lopez helped him see how he could be more. “She knows how to communicate to the masses in ways I never will,” he says. “She has this platform that’s just ginormous, like 200 million on social, over 75% of them millennials. She just sees it. She helps me out all the time when I’m trying to land a point on something. She’s just a wordsmith.”

One of the first things Berkowitz told him was, “We need to figure out who you are. You need to figure out who you are.” After years of wanting and failing to be liked, he discovered a version of himself that the public found genuinely pleasing—and once he did, he couldn’t stop revealing it, especially on social media. “I’m not the person walking around with the camera on myself all day, but he does love it,” says Lopez.

Rodriguez delights in showing that his brand is no longer scandal-ridden Robot. It is now: Baseball geek. Savvy businessman. Hard worker who grinds through every day. Loving family man. Flawed human who makes mistakes.

He does appear to be all those things. Every TV in his many homes is constantly on and tuned to either baseball games or baseball highlights. He works 80-to-100-hour weeks filled with meetings and phone calls and lectures and TV appearances, with his weekends fully accounted for by his ESPN duties. He’ll often hit the gym at one in the morning, fueled by one of the nine cups of coffee he can consume a day, most of them served in A-Rod mugs. Yet, says Cynthia, who divorced Rodriguez in 2008, “When our daughters walk into a room, the world stops for him—and same for them.”

Rodriguez’s message, after the fall, is that he’s just like everybody else, except with nicer possessions and an überfamous fiancée. With Lopez he has become, finally, more than a luxury brand: an aspirational brand, like another pairing of a Yankee and a movie star.

In the entrance hall of his and Lopez’s New York City apartment, a pair of large framed photographs sit side by side on a credenza. One is of the couple, taken by the fashion photographer Mario Testino. The other depicts Joe DiMaggio and Marilyn Monroe.

Not long after Berkowitz began advising Rodriguez, they visited the University of Miami, which Berkowitz attended and Rodriguez almost did. Berkowitz caught his new client wistfully staring at passing students. “I never had one of those,” Rodriguez said.

“What’s that?”

“A backpack.”

A JanSport is not unobtainable by someone of Rodriguez’s means, but he meant it symbolically. There has always been one type of brand that he values more than any other: that of great universities. He remembers where virtually everyone he meets went to college—not just that Cardinals reliever Andrew Miller attended North Carolina, but also that Miller’s wife went to Duke. He has long made a habit of touring campuses around the country, even taking classes at some of them.

It’s because he never enrolled at one himself, as high school shortstops who draw 72 pro scouts to their senior-year games and are picked No. 1 in the draft do not. That—combined with the fact that his father, Victor, walked out on his family by the time Rodriguez was 10—led to deep insecurities that he never fully explored until his suspension, which allowed him time for both introspection and therapy.

Jason Miller/Getty Images; Chuck Solomon

“Remember: I went to prom, and a few months later I’m in Fenway Park, facing Roger Clemens,” he says. “I’m still a boy, and here I am having to play with people who are twice my age. I felt this fake bravado. Physically, I was ready, because I was a man-child. But not emotionally. Then you go on this ascending road for 20 years, along the way you make hundreds of millions of dollars, it’s f------ hard to have some reality, some self-awareness. In college, you get four years to get things out of your system, to grow, to learn. I don’t know what that’s like. The sabbatical—my time off, when I served my suspension—really taught me things that I should have been learning at 19, 20, 21 years old. Things that a good whipping in the butt from my dad would have helped with.”

One thing he did know, early on, is that he never wanted to be poor again, as irrational as that fear eventually became. After his father left, his mother, Lourdes, worked as a secretary during the day and a waitress at night, but the family still had to move every 18 months when the landlord raised the rent. Goddam, if I can ever trade places with the landlord, I will do that, he told himself. He bought his first two-family unit in Miami early in his career, with a down payment of $48,000. He says A-Rod Corp now owns about 10,000 units in 10 states along with a construction arm, investments in a number of gyms and parts of 20 or so other businesses.

Along the way, Rodriguez picked up many mentors who could provide him with the education he lacked and, in some cases, a father figure, too. He gave me a list of contacts I might call to discuss his business acumen, three of them billionaires drawn from the same section of his address book: Mark Mastrov (24-Hour Fitness), Marc Lasry (Avenue Capital) and Mark Cuban (Mark Cuban). I started with a non-Mark/c.

“Alex may give me some credit—but he doesn’t need me,” says Warren Buffett, the world’s third-wealthiest person, on the phone from Omaha. “He’s got a money mind. He just gets things, if they’re business- or money-related.” In 2000, the now 88-year-old had insured a portion of Rodriguez’s record 10-year, $252 million contract with the Rangers. The 25-year-old Rodriguez, delighted, emailed Buffett’s longtime assistant, Debbie Bosanek, to ask for a meeting. So began a series of pilgrimages to Nebraska, for steak and ice cream, that continue 19 years later. 

A cryptocurrency impresario recently paid $4.6 million in a charity auction to have lunch with the Oracle, but Buffett happily agrees to spare 25 minutes gratis to wax about Rodriguez. “Most athletes get gamed,” he says. “They’re pigeons, basically. They don’t have a nose for smelling out the people that are promoters rather than true friends. I don’t know if the term is used anymore, but we used to call them jock-sniffers. They promote partnerships, the young kid is getting checks like he never dreamt of before. Sometimes even their agents may be in cahoots. That has not happened to Alex, and it wouldn’t happen to Alex. He’s got a bulls--- detector that’s pretty damn good.”

Robert Beck

Of Rodriguez’s troubles, Buffett says, “I’ve always said generally, you should behave better in the second half of your life than you do in the first half of your life. You learn more about people as you go through life. You really learn more about yourself. I think that’s been the case with Alex. You and I would not like to be judged by the worst thing we’ve ever done.”

This January, Rodriguez spent two weeks as a guest speaker in lecturer Allison Kluger’s class on strategic pivoting and reputation management at Stanford’s Graduate School of Business. “From crisis comes a decisive moment,” says Kluger. “You can make the moment work for you, or you can crawl into a hole and wait for something else to come. Alex didn’t wait.”

Rodriguez did SoulCycle with the class’s 25 students, and ordered them all a Chipotle dinner (although, as a health nut, he didn’t himself eat a burrito). The highlight of the course, most agreed, was when he narrated his own crisis, though he didn’t get into exactly what substances he ingested or injected, or when or why; he’s never done that, publicly. Even so, all 25 course evaluations offered raves. “Alex’s superpower is his storytelling,” wrote one student. “He was able to engage and connect with every student.”

Acknowledging his failures, it turns out, and elucidating their lessons, was enough to get him to Stanford. 

Jimmy Fallon emerges from Rodriguez’s dressing room at 30 Rock with a theatrical frown on his face. “He’s not gonna do the show,” the Tonight Show host reports, solemnly. Then Fallon breaks into a broad smile. He’s joking. Fallon spots another guest across the hall—a miniature pig, in the arms of its handler—and he’s immediately beside himself. “Oh my god, so cute!” he shouts, as he sprints towards the creature.

The dressing room is done up as a faux cabin: faux antlers over a faux stone fireplace. “Am I first up? Or second?” Rodriguez, sitting in front of a lighted mirror, asks. 

“We don’t do second anymore,” jokes Berkowitz.

A producer has gone over a list of topics with Rodriguez that Fallon will want to cover. Rodriguez has always been a maniacal preparer, sometimes to his own detriment. Early in his Yankees tenure, manager Joe Torre once forbade him from arriving for a 7 p.m. game earlier than six, the message being that Rodriguez didn’t need to exhaust himself hours before first pitch, because he was goddam Alex Rodriguez. He still can’t help preparing, though his goals are now different—in this case, how to most winningly answer Fallon. “Can I have the room with Naomi?” he asks.

Naomi Bagdonas is a frequent Rodriguez consultant who teaches a class at Stanford’s business school called Humor: Serious Business. The course’s central concept is that humor, properly deployed, is a severely under-leveraged asset in the generally dreary corporate world. Being self-deprecating can endear executives to their employees and customers, and it can actually make them seem even more powerful and talented than they are: Who would mock their own flaws if they were significant? It can even make a wildly wealthy athletic legend who is engaged to one of the most famous women in the world seem to be something he never appeared to be in his past life, which is human. 

Rodriguez’s appearance goes flawlessly—almost. He is vigilantly self-deprecating, deflecting Fallon’s constant praise by, among other things, detailing his earnest and fumbling preparations to propose to Lopez and asserting how bad a dancer he is. He recaps his surprise that Barack Obama sent them a card upon their engagement, which Rodriguez had immediately posted to Instagram. He promotes his podcast, inviting Fallon on. He asserts his baseball nerdery and his place in the sport’s firmament, crediting Manfred—his erstwhile Javert—for sending the Red Sox and Yankees to London. “We’re going across the pond to play the greatest game in the world, and we’re leading with our best,” he says. The we’s are notable, and true. Baseball needs Rodriguez. Who else even tenuously associated with the sport could secure 10 minutes on Fallon, let alone in the first slot?

Douglas Gorenstein/NBC/NBCU Photo Bank via Getty Images

Afterward, back in the faux cabin, Berkowitz and Bagdonas are delighted—as is Lopez, who watched the taping via FaceTime. Rodriguez is too, except for one thing: At one point he had failed to come up with the name of the movie Lopez is currently shooting, in which she plays a stripper who takes revenge on her clients. “I f------ forgot the name of the f------ movie,” he says. “F---. It’s Hustlers.” When the show airs that evening, that moment will have been edited out.

Downstairs, his limo is waiting, although it’s more like a limo-van—the 14-foot-long, $160,000 Mercedes Sprinter with two DirecTV screens, quilted captain’s chairs and a chauffeur that ferries him around New York City. But not today. “We’re walking,” he says.

What follows is five blocks of chaos as he briskly strolls up Fifth Avenue. Cars honk at him. A lady walking an assortment of Pomeranians, Chihuahuas and Yorkies nearly drops their leather leashes as she gawks. Pedestrians stop dead in their tracks. There are selfies, autographs and even shouts of “696!” referring to his career home run total. Eventually he reaches his destination, the St. Regis hotel, and walks into a small, empty room off the bar, drawing its purple velvet curtain behind him. Scene.

Why did he choose to walk? Was it for my benefit? Was it for his? “I love the people,” he says. “I don’t think I’ve ever been treated poorly in the streets of New York. I feel like it could be three in the morning, I could walk to the Bronx and people would protect me, if anything.”

After seeing him in public a few times, and observing the way regular people reacted to him and he to them, a thought occurred to me. Might he ever run for office?

“Never,” he says. “Never, never. I don’t think there’s anything I would rather do less. I’m trying to be president of my own home, and I’m having a hard time with that.”

He keeps thinking about it, though. “That’s funny you say that,” he says. “That’s a good question.”

On one day in May, Rodriguez was scheduled to be in Orlando. Demand for the new him is booming, and he was to be the keynote speaker at a conference for hundreds of amped-up middle-market deal-makers. “I have a Ph.D. in failing but a master’s in getting back up,” he would tell the delighted Waldorf ballroom, launching into his prom-to-Fenway and trading-places-with-the-landlord stories, among others I’d by then heard before. 

He would also film part of an episode of Back in the Game, his CNBC series in which he mentors athletes who have fallen on hard times while simultaneously affirming that he has overcome his. He had done episodes with, among others, the former No. 1 NBA draft pick Joe Smith and the former heavyweight champion Evander Holyfield. This one featured Ryan Lochte, the 12-time Olympic medalist who now, Rodriguez would sadly report, is living with his family in a rented two-bedroom apartment, having lost most of his sponsors. 

“His apology was pathetic,” Rodriguez said. “It was awful. Look it up. Half-assed, poorly written Instagram post.” Of course, Lochte’s offense paled in comparison to Rodriguez’s—the swimmer drunkenly messed with a gas station sign during the 2016 Games in Rio—but he was still grateful for Rodriguez’s advice, which included a sharp instruction to never again refer to himself in the third person. “Being with him, learning, having him help me out—it’s amazing what he’s been able to do,” Lochte would say. Rodriguez would invite Lochte to create content for one of the fitness companies A-Rod Corp has invested in, starting him at $15,000 a month.

Rodriguez had decided to make a stop, before he was due in Orlando, to do what he considers to be his most important job of all. He was going to fly to Miami to put his kids to bed, and then drive them to school. 

Rodriguez spends 500 hours a year on his Gulfstream IVSP—nearly three full weeks in the air, which you might too if you had the scratch to buy one. It’s outfitted with 10 plush seats and a bed, as well as endless healthy snacks arrayed next to a single white orchid, WiFi, delicious shrimp cocktail and salmon filets served on green-rimmed Limoges china, and a smooth sound system that plays Rodriguez’s favorite bands, like Bon Jovi and Journey. “Ash!” he shouts out to an assistant, upon boarding. “Coldplay!”

Rodriguez is still buzzing from last night’s Met Gala, to which he wore a different dinner jacket, this one pink. “We had a great table,” he says. “The black guy from The Wire—Idris Elba, yeah, and his new wife. Some famous singer next to me, I don’t know what her name is. Versace—Donatella. We had Kylie and Kendall. And we had an Asian gentleman from Rich Asians, the lead. Kylie was talking about Instagram and her lipstick, and how rich she is.” 

Taylor Hill/FilmMagic

The next morning Rodriguez does drive his kids to school: his daughters Natasha, 14, and Ella, 11—Tashi and Ella Bella, to him—along with Lopez’s twins, Emme and Max, also 11. Lopez is in L.A. rehearsing for her new tour. The kids are all exceedingly polite and don’t complain about having to crowd into the backseat—albeit of Rodriguez’s Mercedes Maybach, which retails starting at $170,750. Natasha helps her younger siblings—all of whom are in the fifth grade at the same private elementary school—study for a science test. 

“See you guys! Crush it on the test!” Rodriguez says to the fifth-graders, after snapping a quick selfie with them for both Lopez and Instagram. Then Natasha, an eighth-grader, is alone in the back.

Rodriguez begins bragging about his daughters, not obnoxiously. Five years ago he gave them money to invest in small stock portfolios. “They have both doubled their money, for sure,” Rodriguez says proudly.

He reveals that Natasha is the president of her middle school and wants to go to Princeton. “I’d like to,” she says. Natasha had herded the family into the car at precisely 7:05 a.m. Unlike her father, she is never late.

“He’s changed,” Natasha says of her dad in recent years. “Totally. He weirdly has more things to worry about. He had a lot to worry about before, but he had a ritual. Now, it’s different. So many different things.”

Both Emme and Max’s dad, Marc Anthony, and Natasha and Ella’s mom, Cynthia, live short walks from Rodriguez’s (and now Lopez’s) house in Coral Gables. Cynthia, who has a master’s in psychology and is remarried with an infant daughter, says that no longer contending with baseball’s daily pressures, plus maturity, have distilled her ex-husband into the person he was all along, deep down. “He didn’t have a chance to develop certain aspects of his adolescence and of his life, and I think marriage is another difficult institution,” she says. “We met when he was 21. What can I say, it didn’t work out. But I’ve always known a part of him that other people didn’t. It’s almost as if the person I knew, that I had a relationship with, is now the dominant personality.”

The Maybach approaches Natasha’s school. “Do you want to let me off here, if you want?” Natasha says, some distance from the entrance. Rodriguez stops the car. “I love you, baby girl. Have fun,” he says.

As she trots off, he says, “She is literally so embarrassed that if it were up to her I’d drop her off like two blocks away.”

Three weeks later Rodriguez is again driving to Natasha’s school, to attend her middle school graduation. Natasha, Rodriguez proudly says, is that evening due to be presented with an award as her class’s most-well-rounded student—“the MVP of the eighth grade.”

In the front passenger seat, Lopez trails her arm out of the open window. “It’s balmy tonight,” she says, dreamily.

“Balmy?” Rodriguez asks. “How do you spell that?”

“B-A-L-M-Y. Balmy.”

“What does it mean?”

“It means when there’s a little bit of a humidity in the air. It’s hot but not scorching. When it feels like there’s a blanket around your skin. Balmy.”

“Use it in a sentence?”

“The air was balmy and thick as we rode to the graduation ceremony.”

“See? She’s a wordsmith,” Rodriguez says admiringly. “I told you.”