Red Sox Confidential

By Doug Bailey | Boston Magazine |

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.

  • mark

    It’s not often that you get to write your own epitaph. Congratulations, Doug, you’ve done it.

    Now, about your other soon-to-be former clients…

  • Lee

    What’s with the jarring edit after the Henry playmate sentence. Looks like an entire paragraph or more was left out.

  • nadiam

    Wow. You must be massive.

  • holden

    reading this was like witnessing a slow death

  • bob

    I’m not a Sox fan – came to this article from Deadspin link – so no ax to grind. However, I’m curious as to why this clown would think that anyone would believe any of what he writes when he essentially admits that his entire job is to spin (aka, lie!). What an awful guy.

  • Bobby

    I am highly skeptical of this story. I don’t believe any of it.

  • Ewillr

    As a transplanted Massachusettsian, I was enthralled reading this piece. I wonder why there was not more focus on the baseball, especially 2004 and 2007. You tip-toe towards that when you wonder which RS player may be taking steriods – more of that would have been better. But, I miss the Red Sox and this has satiated my need for a baseball fix. Thanks

  • Bo

    Pretty Lame. “Tells all” certainly doesn’t mean what it used to. You get more on Twitter.

  • Ryan

    Doug, you come off as incredibly pompous and self-serving in this article. Absolutely nobody cares that the dirt they gave away wasn’t actually from the field. Or that the grass is painted. Or that John Henry may or may not have dated/partied with a playmate. This is a self-serving article that will only self-serve you in preventing you from gaining employment. You may have thrown your PR career away to reveal close to nothing. No one read this article and came away thinking anything different of the Red Sox.
    In summation, you’re awful.

  • Mark

    Did I just read an article, or was I sitting at a bar listening to some drunk guy brag about how he is supposedly the “guy-behind-the-guy” and was once somebody? A weird, rambling, disjointed musing that lacks a lot of things including purpose, audience, and the line “I tied an onion to my belt because it was the style at the time.”

  • Chris

    This was quite the tell-all haha. Sounds like this guys is actually still working for Larry! Besides trying to make himself look like he made the redsox who they are, I really don’t see the point to this article.

  • S

    No ax to grind. Actually, think it’s pretty cool.

  • doug

    Doug Bailey initials = D.B. = Douche Bag

  • fred

    That was the Diet Coke of juicy sports tell-all stories. Just one calorie, not much juice!