The Owner Takes a Wife

Buttoned-down Red Sox owner John Henry revealed a very different side of himself during his topsy-turvy courtship of Linda Pizzuti. (We've got the soul-baring e-mails and love-struck vacation photos to prove it!)

By Emily Kumler | Boston Magazine |
john henry

Henry and Pizzuti in Fenway Park, where they’ll celebrate their wedding late next month. (Photograph by David Yellen)

John Henry stood on the bow of his yacht, wearing a Red Sox T-shirt and tan safari hat, sunscreen covering his nose. Next to him was his fiancée, Linda Pizzuti, in a red tube top that revealed a bit of black bikini underneath. She was explaining to him the history of the Bridge of the Americas, how it connects North America to South. As she read from her guidebook, he looked at her with bemusement. This cruise through the Panama Canal to the Galapagos had been her idea, and now she was serving as eager tour leader.

We’d spent the past three days cruising the canal aboard Henry’s yacht, the Iroquois, a 164-foot vessel with a dozen crew. The trip would be the farthest south Henry had ever ventured, and an immeasurable distance from the posh Mediterranean and Caribbean vacations he was used to. But then, his relationship with Pizzuti has been full of firsts. They were a couple no one could have seen coming—and one that, for a while, had looked doomed. Along the way, Henry, an intensely private man, showed a side of himself that would surprise the Bostonians for whom the 59-year-old Red Sox owner is such an enigmatic figure. I know, because as one of Pizzuti’s closest friends, I had a front-row seat to the whole thing.


Henry began the evening of June 6, 2008, as he did many nights since filing for divorce the previous year: out with the guys. He and Red Sox chairman Tom Werner, a fellow divorcé, met for dinner at Scampo at the Liberty Hotel, one of their favorite haunts. The third member of their party, nightclub owner Ed Kane, was delayed leaving his 25-year Harvard reunion. So to kill time they headed over to the adjacent Alibi bar, where Harley Bilzerian, daughter of Newbury Street boutique owner Alan Bilzerian, was celebrating her 30th birthday.

The shy, somewhat awkward Henry stood in the corner with Werner, who threw open his arms to hug two of Bilzerian’s friends when they came over to say hello. The women were soon joined by a third. Her poise—not to mention her glossy dark hair, endless eyelashes, and ear-to-ear smile—made an immediate impression on Henry.

“John Henry is staring at you,” Amy Belkin, daughter of developer Steve Belkin, told Pizzuti.

“Who’s John Henry?” Pizzuti asked.

Though a Boston native, Pizzuti didn’t follow sports. Feeling uncomfortable with the stranger’s attention, she avoided eye contact. Henry, for his part, kept staring and racking his brain for something clever to say.


Werner, Henry, and Kane call themselves the Cirque du Rire, or Circus of Laughs. They came together after David Ginsberg, vice chairman of the Red Sox, introduced Kane to Henry in the summer of 2007. The group proceeded to spend what was by their count close to 100 straight days together—going to games, eating dinners, watching movies. It’s not often men their age meet comrades they feel so akin to; they think of themselves as brothers. “Between Tom, Ed, and me,” Henry says, “it’s never boring.”

It was 11 p.m. when Kane finally arrived at Alibi with girlfriend Aurora Ransbottom. He asked Henry what he’d missed. “I said, ‘Well, there is an interesting woman over there I was introduced to,'” Henry recalls. He told Kane he couldn’t think of anything to say to her. “Really?” Kane said. “No problem, I’ll send Aurora over.” As Ransbottom approached the woman, “I watched in a little bit of horror,” Henry says.

Taking charge, Ransbottom asked Pizzuti if she would like to join them for a late-night bite at the South End restaurant Stella. Pizzuti shot back with questions: How well did she know these guys? How long had she known them? But after a powwow, our group of friends convinced her to go with the moment. I made her promise to call when she got home.

At Stella, Henry and Kane traded funny stories about celebrating the 2007 World Series win. Pizzuti, not being a fan, didn’t get a lot of their references, but she found their humor disarming. Afterward, she accepted Henry’s offer of a ride home, and sat next to him in his Mercedes coupe, with Kane and Ransbottom squeezed into the back seat. Henry dropped the couple off first. As they walked away arm in arm, Henry said, “Look how in love they are.” After lingering a moment, he drove Pizzuti to her North End apartment.

“Let me know if you’d ever like to go to a baseball game,” he told her, handing her his Red Sox business card. Pizzuti thanked him, but had no intention of taking him up on the offer.

Pizzuti is the kind of person who always remembers your birthday. She’s also the first one to pick up where the conversation left off, as if she’s got a BlackBerry full of the major transitions in your life. When I met her three and a half years ago, there was a group of us who’d recently become close. We’d all grown up in the Hub, and most of us had lived elsewhere after college; now, in our twenties, we were back and eager to redefine ourselves as adults. As it happens, we were also all raised by entrepreneurial fathers who’d taught us to follow our own path, as they had.

Pizzuti’s dad, Don, moved to New England from Italy when he was a teenager. He worked as an engineer for companies like Polaroid and GE while building a real estate portfolio on the side. Eventually he ventured out on his own, and today his development firm is full of Pizzutis, including Linda, 30, and her three older sisters. Linda, who has a master’s in real estate development from MIT and is LEED accredited, focuses on sustainable projects, most recently a group of green townhouses in Lynnfield, where she grew up.

An avid traveler, Pizzuti has eaten dinner atop Mount Kilimanjaro and gone diving in search of shipwrecks in the Philippines. It’s not rare for her to jet to London for a weekend or skip off to Egypt on a family vacation. When she met Henry, she was gearing up for a 10-day visit to Europe.

Pizzuti figured their first encounter would be their last: His fame was enough to put her off, but the fact that he was 29 years older was the real deal-breaker. Her family was old-school Italian, and they’d impressed upon her the importance of reputation. “On paper, it didn’t look great. He was twice my age, and divorced,” she says. “I love Boston—but it’s a small town.”

Still, wanting to be polite, she sent Henry an e-mail thanking him for the meal. He wrote back, claiming MIT president Susan Hockfield had told him at an event that she really hoped Pizzuti wouldn’t retire from the alumni board. Pizzuti realized Henry had Googled her and was using what he’d learned to let her know she was still on his mind. But she didn’t respond, and Henry assumed he wouldn’t see or hear from her again.


And he might not have, if Boston weren’t such a small town.

On June 18, Henry and Pizzuti happened to attend the same event at the new Renaissance Hotel on the waterfront. Pizzuti was immediately approached by Henry’s Circus comrades, armed with questions out of a ninth-grade playbook: Did she like Henry? Why didn’t she return his e-mails? Taken aback, Pizzuti pulled no punches. She told them she was scared of Henry’s public persona.

Eventually, she and Henry found themselves in the same conversation circle. Someone mentioned the previous night’s Red Sox game, and Henry asked Pizzuti, “Did you see it?” “No,” she answered, in a tone intimating she had a life, “I was on a date.” Yet as they talked, she found herself charmed by his wit and intellect. With some help from Werner and Kane, Henry convinced her to join them for a dinner at Via Matta with chef-owner Michael Schlow.

Afterward, they decided to head over to the Estate, one of Kane’s nightclubs. It was pouring outside, big drops plopping onto the sidewalk. Henry rushed out to Via Matta’s patio, grabbed a table umbrella, and, brandishing it with pride, offered Pizzuti shelter. As the group walked up Boylston Street, passersby and drivers stopped and stared at the two, sauntering through the rain under an umbrella fit for Alice in her wonderland.


The clientele of the Estate leans heavily twentysomething, with Red Bull cocktails and short skirts in abundance. That night the club was crowded, and the music deafening. As Henry attempted to chat with Pizzuti, his personal manager handed him earplugs. (The manager always keeps a pair handy, knowing Henry, who used to have his own rock band, is protective of his hearing.) So Pizzuti, wanting to better know this man who’d just sheltered her from the rain in a borrowed patio umbrella, broke out her BlackBerry and showed Henry how to use his for instant messaging. They pinged notes back and forth all night. It was the beginning of what would grow into a modern epistolary romance.

When Pizzuti told Henry about her upcoming trip to Europe, he asked if he could meet her in Paris. Wild as it may seem, this wasn’t the first time a man had made her such an offer. But none had followed through, and all those trips-that-weren’t had made the city symbolic for her. Though impressed by Henry’s eagerness, she politely turned him down.

Nocturnal by nature, Henry is often up until 3 a.m., checking the Japanese markets, strategizing with Sox GM Theo Epstein, or playing with his iRacing simulator, which mimics the cars of his Roush Fenway NASCAR team. This night, though, something else would keep him from sleep. Ever since his divorce, he hadn’t believed romance was in his future, but after he and Pizzuti parted, he headed home to Brookline and fell into bed fully clothed, replaying the evening. He was amazed by the intensity of the feeling.


Kane and Werner knew Henry was smitten. There were no topics off-limits among the three men.

Henry and Werner met in 2001, the year Henry (who had made his fortune in futures trading) was considering purchasing the Anaheim Angels. When he lost interest in that deal, he contacted his friend Larry Lucchino, whom Henry had gotten to know while the owner of the Florida Marlins. Lucchino was at the time working with Werner to bid on the Red Sox. Henry sat down with Lucchino late one night in New York to discuss the Sox, then flew to L.A. to talk with Werner.

“We went to dinner,” recalls Henry, “and when we were leaving I said, ‘You’re a lucky man, Thomas: bidding for the Red Sox, an ĂĽber-successful TV production company, three kids. You’re loved by everyone I know who knows you. And you’re dating Katie Couric.'” To which Werner jokingly replied, “They’re the lucky ones!” “I soon found out,” adds Henry, “he was pretty much dead-on right.”

Neither of them thought they’d wind up single at the same time. “I didn’t think we could get any closer, but we did,” Henry says.

Kane, Werner, and Henry talked a lot during the summer of 2008 about dating in general and Pizzuti in particular. Kane argued that if age was really the hang-up, they could consider Pizzuti “30 with an asterisk.”

“Right out of the gate, I didn’t think age should be a big deal,” Kane says. “She’s smart and accomplished. And honestly, John is hilarious. People think of him as a business guy, but underneath all that he’s a really funny, warm guy.” What’s more, Kane respected Pizzuti’s reluctance. “She was as cautious as she was curious. I admired that.”

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Pizzuti always wanted an outdoor wedding reception under a big white tent. Henry, it just so happens, has access to a suitable venue. (Photograph by David Yellen)

Pizzuti soon left for Europe, and Henry went on with his life. A week after he and Werner watched the Celtics’ championship win over the Lakers from his courtside seats, they hosted a victory bash at Fenway. During the festivities, it began to rain.

That night, Henry e-mailed Pizzuti.

Dear Linda,

A man needs a muse. Well, he doesn’t really. He doesn’t need nearly as much as he generally thinks he does. A man is greedy. Greedy for what he doesn’t think he has and what he thinks he wants.

We probably wouldn’t have wandered far beyond the basic necessities without that pushing us. Progress is one of its most important byproducts.

So you will ask, “Why are you writing this?” Because a brief encounter-and-a-half with you gave a cool spin to this little blue planet from my vantage point.

We feted the Celtics tonight and the skies opened. The sun emerged and created a giant rainbow between the city and the park. We were transfixed.
You only saw it if you were in the right place. I was in the right place when I noticed you.

I barely know you. I don’t have any illusions about capturing your heart. But the world is brighter, better, lighter and warmer when a man imbues a woman he knows—even tabula rasa—with the attributes I believe reside in you. It’s the small things that ultimately matter. The subtle things.

I am honest. I don’t play games. And I see no reason not to say that I’ve been smitten by you and you’ve done me a great service.

You’ve very innocently made my world brighter, better, lighter and warmer.

So thanks.

No response is necessary because a man doesn’t need nearly as much as he thinks he does.

But Henry waited for her response anyway. When it finally came, it wasn’t quite what he’d hoped for.

A man may not need as much as he thinks he does, but courage and honesty should be acknowledged. I am not so naive as to believe I actually possess the qualities you attribute to me. But thank you.


After earning her master’s at age 26, Pizzuti—determined to avoid the procession into marriage, suburbia, and children—broke up with her then-fiancĂ© and moved to the North End. Living alone and loving it, she was up early every morning to hit the gym or a dance studio for salsa lessons; after long workdays she juggled a full calendar of charity and social commitments. Trying to keep track of her could be exhausting.

In Prague, partway through her trip to Europe, Pizzuti found herself thinking about Henry. He had followed up after her e-mail with, “Just struck me—the similarities to Cyrano. Except the young Adonis is a BlackBerry”; she joked back that thankfully he didn’t have Cyrano’s legendarily big nose. She liked the highbrow banter, and she liked Henry’s willingness to bare his soul. By the time she landed in Boston, she had convinced herself it would be okay to be friends.

But nothing more: When Henry suggested they go on a date, she wrote back, “It would be a fantastically bad idea to go out with you. It would lead to trouble and gossip in a small town.” Turning to self-deprecation, he responded with a list of additional reasons she should refuse, including “My expiration date was about 10 years ago.” Won over, Pizzuti agreed to meet him the following week at the Golden Goose market in the North End, where they would buy supplies for a cooking lesson on his yacht.

Three days before their “friend date,” as Pizzuti dubbed it, Henry met Kane at the 1369 Coffee House in Central Square. (Henry, who’d only recently started drinking coffee, had become an effusive fan of the place—even flying one of its managers to his house in Boca Raton to train his staff on brewing techniques.) Afterward, Henry drove to the North End for dinner with Werner and his daughter, Amanda. He got lost and called Pizzuti for directions. She guided him in, but he was so late that the Werners had left. So he called again: “I’m across the street at Florentine. Come down!” Pizzuti refused, telling him she’d see him in three days as they’d planned, yet 45 minutes later she appeared at the restaurant. They strolled the neighborhood for hours, and at one point Henry tried to take her hand. She had to explain to him that it was too intimate for friends.

When Henry and Pizzuti met the cooking instructor at the Golden Goose, she realized it had been years since Henry had been to a grocery store, and probably decades since he’d cooked. But he seemed thrilled to go along with whatever she wanted to do. On the boat, Henry presented her with custom aprons: for her, “Ms. Pizzazz” (his nickname for her), and for himself, “Fantastically Bad Idea.”

The next night, July 10, they attended Sox pitcher Josh Beckett’s Beckett Bowl fundraiser, making a concerted effort not to be seen together. They followed up with a walk around the Bunker Hill Monument—this time, they held hands—and a late dinner at the Franklin CafĂ©, where a waiter told Henry’s manager (Pizzuti was still insisting on a chaperone) that the couple looked madly in love.

A week later, Werner convinced Pizzuti to travel to L.A. to rendezvous with the Circus, who would all be in town while the Sox played the Angels. Werner’s house there sits on a golf course with views of the rolling fairways, which inspired Henry to buy a tent and—mindful of the rules of this evolving “friends that hold hands” relationship—eight sleeping bags for a backyard campout. “John thought it would be romantic,” Werner says. “I told him that was all well and good, but I preferred to sleep in my bed. I offered to make them breakfast in the house the next morning.”

That night, in what Pizzuti regards as quintessential Henry, he had a debate with himself, out loud, about whether he was in love. He concluded that the answer was probably no. She thought, Okay, great, thanks, did I ask if you were? But the next evening, after screening Mamma Mia! at the home of a producer friend of Werner’s, Henry changed his mind. “I must be in love,” he announced, “because there’s no way I would have sat through that movie if Ms. Pizzazz hadn’t been next to me!”

For her part, Pizzuti was learning to take his directness in stride. “If he’s thinking something, he shares it,” she says. “I thought he was a bit nuts. Mostly I just laughed at his declarations.”

When Henry and Pizzuti were together, they felt as if they were a perfect match: They shared the same intellectual curiosity, the same zest for life, even the same love of Italian food. But when they were apart, family, friends, and fear of the press would bring their big age difference to the fore. Pizzuti’s parents wanted their daughter to grow old alongside her husband. Our group of friends worried she’d have to fit herself into his life, rather than building one together with him.

Pizzuti’s already-packed schedule became even more hectic as she joined Henry’s world. When the Sox had home games, she’d put in a long day at work, then meet Henry and their friends at Fenway. They’d often go to dinner afterward, getting home around 2 in the morning. Then she’d wake up at dawn and do it all over again. Pizzuti was still protecting herself, taking pains to maintain her independence, but by the end of the summer, I was wondering if she was really enjoying herself.

Kane remembers what he saw as the turning point for Pizzuti and Henry: “She wants to be Linda Pizzuti, not Linda Henry. I think once she realized it wasn’t his intention to form her, their relationship took off. He appreciates independent thinkers.” I knew it was serious when Pizzuti told me she was going to Paris with Henry on a double date with Kane and Ransbottom. This was a big gesture for her, considering the pedestal she’d put that city on. She was announcing that she trusted him.

After Paris, the two were inseparable. For her birthday in early September, Henry arranged for a helicopter tour of Manhattan and dinner at the Four Seasons, topped off with a cotton-candy dessert he had special-ordered. Before the night was over, though, the age difference came up again. Pizzuti’s parents were still trying to talk her out of the relationship; she couldn’t entirely ignore where they were coming from.

Henry’s head was spinning. But he also felt protective toward Pizzuti, and was willing to end things if the age difference proved insurmountable. After hours of emotional back and forth, they at last reached a breakthrough. “There are no guarantees in life,” Pizzuti recalls deciding. “I could get hit by a bus tomorrow. I’m not going to walk away from this incredibly special connection for the fear that I could outlive him, or that society will disapprove. I know that people have and will judge me and make assumptions about my intentions. But this is love.” She finally declared that night that she loved him.

Now she just needed to convince her family. Henry and Pizzuti hosted her parents at Sox games, and the Pizzutis, in turn, had invited Henry to dinner at the Fairmont Copley Plaza and to a Pops concert (Henry and Pizzuti ducked out to hit a Madonna show), but that hadn’t been enough. So Henry joined the family’s “chaotic” (their words) annual pilgrimage to Disney World, celebrating Thanksgiving there with Pizzuti’s mom and dad, and her sisters and their young children. Recognizing the effort Henry was making—and how happy their daughter was when she was with him—the Pizzutis came around at last.

The proposal came one afternoon last December, while they were in New York to honor Henry’s Roush Fenway drivers at the NASCAR awards dinner. In an elevator at the Four Seasons, he took Pizzuti’s hands and said, almost in passing, “Don’t answer today or tomorrow, but will you marry me?” About two weeks later, she asked, as casually as she could, “So, did you really propose to me that day in New York?”

“What did it seem like to you?” Henry said.

“Sort of like a letter of intent.”

The couple has set a date for late June. Pizzuti always wanted an outdoor reception under a big white tent, and Henry, as it happens, has access to a suitable venue. After a small, family-only ceremony, they’ll host friends at a party in the Fenway outfield. Pizzuti, who tried on and rejected some 50 dresses in New York, will wear a gown made by Boston designer Michael De Paulo, who is crafting an Old Hollywood–style number for her. But maybe because she’s been a bridesmaid enough times to go pro, or maybe because of Henry’s calming influence, not much about the wedding planning seems to be fazing her.


I was the first of our friends to see Pizzuti wearing her ring. It was Super Bowl weekend (it took the couple a while to find the right setting) and we were sitting by the pool at the estate they now share in Boca Raton. Later that night they entertained a few dozen guests at the on-site bar, which is decorated with Red Sox World Series trophies and the broken champagne bottle used to christen Henry’s boat. News of their engagement had come out in the Boston gossip columns, and guests offered their congratulations as Pizzuti floated around the room.

“John has helped me to appreciate the moment,” she says now. “I tend to be overscheduled, but he has a better balance in his life. He’ll savor a sunset, a beautiful day, a laugh, a warm feeling. He has slowed me down a bit.”

Still, Pizzuti won’t let herself, or Henry, slow down too much. Two weeks after the Super Bowl party, we were off on the cruise through the Panama Canal. One day Pizzuti arranged for us to take a canopy tour in the jungle; the next she had us off exploring the streets of Panama City. Between those excursions, I watched as she and Henry practiced their rumba to a Beatles mix he had made for her. She jokes that their first dance as newlyweds might be performed by body doubles. They’re taking dance lessons, and, while they’re not ready for prime time, they crack each other up the whole time.

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