The Owner Takes a Wife

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 über-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.”