The Owner Takes a Wife
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."