The Owner Takes a Wife

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.

See a slideshow of photos featuring Henry and Pizzuti's romance. 

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.