Red Sox Confidential

For six seasons, I witnessed — and helped spin — sports history as one of the media strategists for the Red Sox. From the petty feuds and behind-the-scenes politicking to the unbelievable championships (and gorilla suits!), I had a front-row seat to it all.

By Doug Bailey | Boston Magazine |
red sox confidential

Illustration by Kagan McLeod

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.

Larry Lucchino red sox confidential

Illustration by Kagan McLeod

Anyway, it’s hard to believe now, but Henry, Werner, and Lucchino were pariahs in Boston when they first showed up in town trying to buy the Sox. (Maybe it’s not so hard to believe, actually, considering recent events. The worm can turn pretty quickly around here.) The press at the time treated them like foreign interlopers with no understanding of New England tradition and culture. I personally couldn’t understand why the media were lining up behind a local hot dog vendor (Joe O’Donnell) or a parking lot baron (Frank McCourt) instead of these experienced baseball heads — especially considering that what was now known as the Henry group was the only bidder for the team promising to preserve Fenway Park. Then again, I did  have an interest in them getting the club.

Sometime around Thanksgiving in 2001, with Henry, Werner, and Lucchino reeling from the carpetbagger charges, Larry Rasky called a meeting to strategize what we could do to emphasize the fact that there were also local people in the bidding group. Lucchino, who undoubtedly was taking signals from baseball commissioner Bud Selig, had asked Rasky to come up with a plan to showcase high-profile local participants such as Arnold Worldwide CEO Ed Eskandarian, former Maine Senator George Mitchell, and TJX CEO Ben Cammarata. Someone came up with the idea of putting everyone on a bus and driving them around town, stopping off at select tourist attractions so the media could photograph and interview the outsiders mingling with the locals in the group. It was a terrible plan — I could envision Dan Shaughnessy pointing out that these guys couldn’t even find Fenway Park without a Magical Mystery Tour guide.

So I offered an alternative: Set up the prospective owners in a hotel room downtown for some supposed meeting, then leak it to the press that should they park their cameras in the hotel lobby at, oh, 5:40 p.m. — after the Patriots game — they just might catch the bidding group emerging from an elevator and be able to buttonhole them with questions. The tactic worked beautifully. Without a news release or official announcement, every TV station, print outlet, and even some radio stations covered the “meeting.” Exiting the elevator with the newly enlisted local partners, Lucchino surveyed the phalanx of cameras and reporters and whispered, “I heard you were good, Rasky. I didn’t know you were this good.” That shot ran on the 6 p.m. and 11 p.m. news that Sunday and most of the next day — the day that the final Red Sox bids were due to be submitted to Major League Baseball.

With the Henry/Werner group prevailing, Rasky Baerlein became the official PR outfit of the Boston Red Sox. Our first major assignment was to help set up visits by the new owners to the other New England states, where we would hold rallies, introduce them to the fans, and meet with local officials, pols, and business leaders. At each stop, we’d give away jackets, balls, hats, pennants, and trinkets. One day, I got an idea for another souvenir while roaming around Fenway. I noticed a pile of 50-pound bags of crushed brick stacked against the walls in the tunnel between the Sox dugout and the clubhouse. I asked a groundskeeper what they were. “The warning track and the infield,” he said, like it was one of the dumbest questions he’d ever heard.

It turns out that Fenway dirt isn’t dirt at all. In the infield, it’s a substance called “Turface,” a brick-red clay material that Henry had ordered to match the color of the crushed brick that makes up the warning track in the outfield. I brought this up at a meeting, and we landed on the idea of giving away little plastic bags of the stuff, labeling it authentic Fenway Park infield dirt. “Dirt,” Lucchino said, twisting up his face. “We’re going to give our fans bags of dirt?” His reaction seemed to sink the notion right there. But on the next trip, to New Hampshire, we brought along about 100 little bags of the dirt — which of course had never been closer to the Fenway infield than the dugout. But that didn’t matter. The bags disappeared the instant they were shown off to the admiring crowd. On our next trip we packed even more bags, but ran out just as fast. The enthusiasm and rabid intensity of fans throughout New England defied logic and clearly awed the new owners, who were realizing first-hand what everyone in the league had told — or warned — them: It’s different in Boston.

john henry red sox confidential

Illustration by Kagan McLeod

It’s also expensive, from buying the club to fielding a team that can compete with the Yankees. So it’s understandable that marketing the Sox and finding new revenue streams consumed Lucchino and his business-side minions in the early years. I remember seeing a high-definition telecast of a Sox game for the first time on NESN and remarking to a marketing executive that the picture was so clear you could make out individual blades of grass on the field. “Yup,” the exec responded, smiling broadly, “and we can put a corporate logo on every one.”

The grass was always a big deal with the press. I once got a call from a Globe reporter who wanted to do a lawn and garden feature and needed some secrets from groundskeeper Dave Mellor on how he keeps Fenway’s grass looking so green. The reporter happened to catch me as I was meeting with team executives in a suite overlooking the park one day in early April. I could see Mellor and his crew on the field — currently brown like spring grass everywhere in New England — working to ready Fenway for Opening Day. Someone was spraying a liquid, transforming the dingy grass into a healthy-looking green. Paint, I thought to myself. That’s the secret.


Some of the early fun and thrilling discovery from that first year came to a screeching halt with the sudden and disastrous end to the 2003 season, when the Sox lost yet again to the Yankees in agonizing fashion. After that, 4 Yawkey Way — the team’s corporate offices — became more serious, and Rasky Baerlein’s role in working with the club grew more solidified.

Each day, I took part in a “media” meeting in Lucchino’s office. We’d review the morning’s news coverage and plan press strategies. I looked forward to these meetings and enjoyed the back-and-forth with Lucchino and his team. I found Lucchino nothing like his reputation as a hard-edged, demanding, volatile taskmaster. That’s certainly been the picture painted of him lately, with many observers speculating that he drove Theo Epstein from the club. Lucchino did sometimes come across as tough, but for the most part he would invite criticism (he once whacked me with a rolled-up newspaper when, after he asked for a constructive critique on how he’d done with a speech, I sucked up and complimented him), seek input, and gather all available information before making decisions. He could be impatient and railed against the slowness of progress or the inability to complete certain tasks on time. But it didn’t appear to me that people were afraid to speak their minds. No one cowered in his presence.

Actually, I saw evidence of an outsize temper only twice. The first time was when we were driving to an appointment with Mayor Menino and Lucchino was certain I had taken a wrong turn and he was going to arrive late (I hadn’t and he didn’t). The second time was in August 2005, just after the Sox had backed out of a trade with the Colorado Rockies, a move that made the club look bad to many observers. My understanding was that it was Epstein himself who’d wanted to back out of the deal, but that he and Lucchino had cooked up a face-saving cover story that involved upper management supposedly overruling the trade. Soon after, I was in Lucchino’s suite overlooking the park during a rare weekday afternoon game, watching Epstein being interviewed on TV about the deal. Epstein put the blame for its collapse squarely on Lucchino’s shoulders, which sent the CEO into red-faced paroxysms. Lucchino apparently wasn’t expecting to be so directly and completely thrown under the bus. The issue would soon rise again, just after the season ended, and become the centerpiece of Epstein’s decision to abruptly quit the team on Halloween of 2005 (the famous gorilla-suit escape). When Epstein agreed to come back three months later, one of his conditions was that Lucchino’s daily media meetings be shut down. Epstein had always had a standing invitation to attend those meetings but never came, apparently believing we were spending our time devising ways to bolster Lucchino’s image and undercut his. Clearly, factions were forming on Yawkey Way, roughly around one group that felt Lucchino had amassed too much power and was butting into everything, particularly baseball operations, and another that believed Epstein was more lucky than talented and owed his entire baseball existence to Lucchino. The conflict led to some tense moments and intensified the club’s already ingrained obsession with unauthorized leaks to the press.

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Photo by Al Bello/Getty Images Sport

Along with the daily media meeting, I also attended a weekly gathering related to the renovation of the ballpark, as well as to real estate and neighborhood issues. You don’t tend to hear as much about these kinds of things as you do about where the Sox are in the standings, or who’s drinking beer in the clubhouse, but believe me, the team is sensitive to how its business dealings are portrayed in the press.

By early 2005, the new owners were ready to commit to staying in Fenway rather than building a new stadium. But the issue was complicated because the team felt the infrastructure around the park needed substantial — and expensive — improvements. It was a delicate topic, one that still reverberates, because the Sox ownership badly wanted to appear accommodating, wanted to showcase the hundreds of millions of its own money it would be putting into the renovations, while at the same time downplaying its desire for public contributions. They were well aware of the beating Robert Kraft had taken in the press when he tried to obtain taxpayer dollars for a new stadium for the Patriots. Just broaching the topic in the city, we knew, could set off a flurry of negative press and publicity for the Sox, even though the team had finally broken the curse and won the World Series. So how to proceed?

In 2000 — before the Henry/Werner group bought the team — the state legislature had approved spending more than $300 million on improvements around the park as part of the then-owner’s plan to build a new stadium. That plan fizzled, and with it the public funding, but now Henry, Werner, and Lucchino wanted to either revive the state’s financial incentives package or quietly win a new round of funding. The finesse with which this had to be accomplished could not be overstated. There were some around the table at these meetings who argued vociferously to simply tie the Fenway Park commitment to public funds. In other words: “We’ll only stay and renovate Fenway if we receive taxpayer assistance for infrastructure improvements.” Lucchino overruled them. The Red Sox would make the commitment to Fenway Park regardless of the infrastructure issue. Gradually, a media plan emerged: The team would guarantee that baseball would be played in Fenway on its 100th anniversary in 2012; highlight all of  the money the new owners had already spent — and were going to spend — on improving the park; and extend an offer to help the state with infrastructure improvements. Implicit in that offer, of course, was that the state would kick in money, too.

The whole thing was going to be laid out at a press conference at Fenway on March 23, less than a month before the start of the 2005 season. It was a solid plan and might have gone off without a hitch, but it was nearly sunk when an overeager associate decided to give an exclusive advance to Globe columnist Joan Vennochi in a wrong-headed attempt to win some positive press. Joan is a friend of mine and a true baseball fan, but she is a fierce opponent of public financing for professional sports teams. In fact, she’d been one of Kraft’s most dogged critics during his quest for taxpayer money to build a stadium in Boston. When the paper hit the door that morning, you didn’t even need to read the column to know what it said. The headline told it all: “No Public Money for Red Sox.” It would take months to recover from that blunder, which seriously set back the club’s plans for taxpayer support. In the end, the team got less than $100 million.


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.


The Red Sox of 2003 and 2004 were filled with colorful characters — including the guy whose trade from the team is often credited with helping the club at last win a championship.

I’ll never forget the time, at some point after the space shuttle Columbia disaster in 2003, that NASA arranged for two female astronauts to throw out the ceremonial first pitch at a Sox home game and deliver a brief tribute to their fallen colleagues. I happened to be an acquaintance of one of the visiting astronauts — Cady Coleman — so I volunteered to shepherd the two women through Fenway and onto the diamond. I ushered Coleman and Stephanie Wilson down to the field, but a rain delay forced us to wait for more than an hour in the Sox dugout. Players wandered around us, trying to relax as the umpires and owners huddled to decide whether to play the game. I didn’t normally mingle with the players, so it was a bit of a thrill to be sitting wedged among Nomar Garciaparra, Tim Wakefield, and other stars. Nomar curiously watched my interaction with the two women, who were dressed in their bright-blue flight suits, and finally nudged me and asked who they were. I explained that they were astronauts. “Hey,” Nomar replied, “I saw this show on Fox that said we never really went to the moon. The whole thing was faked. Can I talk to her about that?”

“Sure,” I said, eager to witness this conversation.

Coleman diplomatically handled the inquiry from Nomar. “I’ve heard about that,” she said, “but it would have to be an enormous conspiracy.”

“Did you see the show?” he quickly rejoined. “It was really convincing…. I don’t know.”

She hadn’t seen the show and looked plaintively at me as other players began to join the conversation. “Hey,” I said, trying to change the subject. “Cady is going to spend six months on the International Space Station. Talk about training for the big show.”

Intrigued, Nomar asked about the size of the space station. “It’s really big,” Coleman said.

“Is it as big as Fenway Park?” Nomar asked.

“No, not that big,” Coleman replied. Then she started looking around for ways to illustrate the dimensions of the orbiting vehicle.“How far is it from home plate to first base?” she finally asked. About six players yelled in unison: “Ninety feet.”

“It’s about that size,” she told them.

“That’s not big,” Nomar said. “That’s small.”


After the end of the 2007 World Series, I began thinking about leaving Rasky Baerlein and starting a new chapter in my PR career. That would mean giving up my work with the Red Sox — a thrilling, once-in-a-lifetime experience — but after six great seasons I couldn’t really imagine it getting any better.

What I was especially going to miss, I knew, was the ability to share my access and privilege with other people. Like the time I escorted a pair of German tourists into a closed Fenway and took them onto the field (when they flatteringly mistook me for a player, I signed “Doug Mirabelli” in their autograph book), or when I got Jason Varitek to sign my niece’s hat, or when I brought my older son into the team’s clubhouse after the 2007 ALCS victory and he was able to pose for pictures with an agreeable Jonathan Papelbon.

My favorite memory, though, was the warm September night when the Sox clinched the wild card on the last home game of the 2003 season. After the final out was made and the on-field celebration had begun, a security guard spotted my ID and motioned for me to step onto the field. The next thing I knew I was high-fiving players and jumping up and down with joy along with everyone else. I even danced a jig on the pitcher’s mound with my former Globe colleague Meg Vaillancourt, who had become head of the Red Sox Foundation. Running into the clubhouse for some champagne, I had my nice blue suit ruined when outfielder Gabe Kapler doused me with foamy spray from his bottle of bubbly. Returning to the field, I walked slowly down the first-base side, where hundreds of fans were holding empty beer cups in their outstretched hands. I happily poured them champagne from my bottle. At one point, I happened to turn to look at the Jumbotron, and there I saw myself quenching the thirst of that happy throng. The next day my e-mail inbox was filled with messages from people I hadn’t seen or heard from in years. They’d been watching the game and couldn’t understand what the hell this small-town kid from Maine was doing celebrating on their TV screen.

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