Red Sox Confidential

I ENJOYED A GOOD working relationship with Lucchino and sometimes with Tom Werner, but it was a different story with John Henry. He was distant and aloof, and there were only rare instances in which he needed to interact with us at Rasky Baerlein. So up through the 2004 season, I’d had very little contact with him. But in the spring of 2005 I was asked to accompany Henry to a Lowell Spinners game, where he was going to hand out World Series rings to the owners and coaches of the Sox’s minor league affiliate. I had no idea why the assignment fell to me, but on a warm spring morning, Henry’s driver picked me up at the park and we went to Brookline to collect the Sox chairman at his home.

No one told Henry that I was coming, so my showing up at his manse seemed to throw him off balance. On the ride up to Lowell he mostly fiddled with his BlackBerry, made calls, and flipped through some reading material. At the stadium, the pre-game ring ceremony was actually quite emotional. Henry read off the names of the owners and coaches, and I found myself handing each one of them a little box containing their ring. Afterward, Henry and I sat together in the cheap seats and watched the entire game, talking about whether some of the cheesy between-inning entertainment, like dot races and hot dog shootouts, could work in Fenway. We concluded that Fenway traditions, and fans, wouldn’t allow such modern diversions, even if the kids would love them.

In the car on the way home, we chatted about which Sox players might have been on steroids before the crackdown, and discussed the team’s prospects for the season that was just unfolding. It was a really enjoyable day, and my impression of Henry changed dramatically because of it.

Two weeks later I ran into my new friend at an event at Fenway Park. Walking toward me, he extended his hand and offered a limp handshake. “Hi,” he said, introducing himself, “I’m John Henry.”

A couple of years later, I got an odd call from Lucchino during the 2007 World Series. The Sox had just beaten the Colorado Rockies in Game 2 of the series, and I was in my car heading home. On the phone, Lucchino was in a playful mood, asking me how the game had turned out. He joked that he’d been too busy with another matter to notice, then asked if I could come to a meeting at Fenway with him and Henry.

“When?” I asked, checking the time. It was about 1:30 a.m.

“Right now,” he barked. Before I could respond, he laughed and said, “No, tomorrow morning, 10 a.m.  See you there.”

Arriving at a deserted Fenway the next morning, I waited patiently in a meeting room. And waited. Henry’s secretary finally came in and said Henry had forgotten about the meeting, and was only just now getting out of bed. Lucchino showed up and was pleased that he had some time to brief me before Henry arrived. The issue was a sensitive one. Henry had just separated from his wife and was reportedly hitting the clubs. The Globe and the Herald’s Inside Track seemed obsessed with identifying his companions, and we needed a strategy to deal with it. The Globe had even reported that Henry was seen at a party at the Estate nightclub in which Playboy Playmates were present, the implication being that he was seriously playing the field. When Henry eventually arrived — our wait had been lengthened by a wrong turn he somehow took while driving to the park — he seemed deflated and confused about why he needed any PR counseling at all. He didn’t consider himself a celebrity, he said, and couldn’t see why anyone would care whom he was seeing. “I see they put the camera on me during games sometimes and don’t really know why.”

I said something about how if he was socializing with Playboy Playmates, keeping him out of the press was going to be problematic. He simply scoffed and insisted he’d never dated a Playmate.