Red Sox Confidential

By Doug Bailey | Boston Magazine |

IN 2001, I BECAME one of the Globe’s first buyout babies, offered a full year’s salary and all benefits to leave the paper. After two decades in journalism, it was my intention to take the time to write my screenplay, become a rock star, or just live like a retiree for a while. Two months later, though, I was convinced to join the public relations firm Rasky Baerlein by its affable chairman, Larry Rasky. I was a little hesitant to switch to the “dark side” of PR, but Rasky dangled one especially persuasive carrot: His firm was doing work for two guys who were trying to buy the Red Sox, Les Otten and Tom Werner, and if they managed to get the team, I’d be working for the firm that repped the city’s most beloved institution.

And for the most part, that’s exactly what happened. From the winter of 2001 until the end of 2007, I was a flack for the Sox. In my capacity as senior vice president at Rasky Baerlein, I consulted with the team’s owners about their public relations and strategic communications. For a New England kid, six seasons of reporting to Fenway Park each morning kept me in a constant state of exhilaration. I was the envy of colleagues and family members. I had a badge that gave me total access to Fenway Park at any time. I was present at nearly every major Sox milestone in the first six years of the new millennium — including two World Series. I was on a first-name basis with the top executives and sometimes rubbed elbows with players. Though I tried to maintain some semblance of professional behavior, most of the time I was just thinking: “How the fuck did I get here?”

Those days have been running through my mind quite a bit lately, now that there’s so much turmoil swirling around the club again. Francona’s gone. Theo’s gone, supposedly driven out by a meddling Larry Lucchino — who, if the rumors are to be believed, then turned around and threw Theo’s replacement, Ben Cherington, under the bus by rejecting his choice for a new manager. It’s been quite a while since I’ve had any knowledge of the goings-on over there on Yawkey Way, but I tend to doubt it all went down like that. I got to know these people pretty well over the years, got to see them at their best and their worst, and if there’s one thing I learned, it’s that when it comes to the Boston Red Sox,
nothing is ever as  simple as it seems.

I STARTED AT Rasky Baerlein on Tuesday, September 4, 2001, assigned to help build a crisis communications practice. For exactly one week, things were pretty slow. The Tuesday after I started, though, was 9/11, and the next thing I knew I was reviewing security contingencies for the giant LNG tanker that Mayor Menino felt was a terrorism target; writing a crisis plan for a junk-mail company whose business was threatened by the anthrax scare; and consulting with several other organizations whose crisis-planning policies were suddenly sorely lacking.

Rasky may have lured me with promises of the Red Sox, but it was turning out that my involvement with the group trying to buy the team was minimal at best. Thankfully, that changed pretty quickly. Because of my newspaper background, I was wrangled one day to help “media train” Les Otten, a guy I eventually got to know a little and like, but who needed some polishing as he prepared to make the case that he and Tom Werner were credible buyers for the Sox. Otten was essentially a ski bum who’d done well and bought a string of New England ski resorts in a novel quest to consolidate and conglomerate that fractured industry. Successive snowless seasons had all but ruined his plans, however, and shares in the company had fallen below $2.

Otten and Werner’s plan to buy the team took an abrupt turn when the bidding price went from around $300 million to $700 million, an amount beyond the financial wherewithal of both men. That’s when corporate titans John Henry, Larry Lucchino, and the New York Times Company entered the scene, eventually overshadowing the original Werner/Otten group. They wound up getting the team, of course, but Otten’s role was severely diminished. His sometimes-clumsy attempts to involve himself in team governance — arriving uninvited for management meetings, and even showing up at spring training in full Red Sox uniform to take grounders from Johnny Pesky — made him persona non grata, and his eventual severance from the team was awkward and a bit messy. That was unfortunate. The world needs dreamers, and Otten dreams big.

 Illustrations by Kagan McLeod

  • 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!