By Bill Simmons
Page 2

Let's get this out of the way first …

From a pure baseball standpoint, I thought Theo Epstein was a little overrated. Just a little.

So I'm not in full-fledged, "Oh my God, we lost Theo!" panic mode like some other Boston fans. I liked everything I ever read about Theo, thought he did a decent job, loved having a local guy running the team, even appreciated how he avoided the spotlight and seemed devoted to his job -- eschewing ego-related perks like frequent TV appearances, radio shows, cheapie books, etc. Considering he was hired as Boston's general manager at age 28, before he was experienced enough to run a team, looking back, there's no question he acquitted himself well.

With that said, you can't ignore the fact that Theo was staggeringly fortunate over the past three seasons. Consider …

• Many of the blockbuster moves he wanted to make over that time (Jose Contreras before 2003, Javy Vazquez and the Manny/A-Rod and Nomar/Magglio Ordonez trades before 2004, Carl Pavano and Adrian Beltre before 2005) would have worked out poorly in the end. In each case, his Plan B or C (keeping Manny, getting Curt Schilling and Orlando Cabrera) ended up being a better move than his original intention. Is that skill, is that luck, or is it a little of both? You tell me.

• Last winter, when the franchise had a free pass with fans to either A) bring back most of the championship team, or B) remake the franchise for the next 10 years, the Red Sox chose the curious direction of dumping certain key guys (Lowe, Pedro, Cabrera, Roberts) and spending too much money on iffy free agents (Edgar Renteria and Matt Clement), handicapping the team's payroll for the immediate future and leaving the team in the curious position of losing more World Series heroes this offseason (definitely Johnny Damon, possibly Manny) to keep guys who hadn't won anything with the team.

• He did a subpar job with the 2005 roster, remaining loyal with some guys too long during the season (Foulke, Bellhorn, Embree, Millar) and not making any of those Shawn Chacon/Aaron Small-type moves to keep the team rolling (with the exception of the Tony Graffanino trade). And that misguided loyalty raised the question, "Why weren't they as loyal to guys like Cabrera and Roberts?"

• If Posada's throw to second base in Game 4 of last year's ALCS is 1/10th of a second quicker, Roberts doesn't steal second and young Theo suddenly isn't getting a free ride for the A-Rod saga, the Nomar trade, the Renteria signing and everything else.

Did I like him? Absolutely.

Do I believe that he would have grown into this job and been an absolute asset down the line? No question.

Are we losing a young Red Auerbach here? Umm … it's a little early to say that, don't you think?

Let's face it, it's much easier to run a baseball team when you have $110-120 million to spend every season -- for instance, on a mid-market team like the A's, Renteria's $40 million contract would have been a crippling mistake. In Boston, you can live with those screwups, just like you can take expensive fliers on injury guys (Wade Miller, Matt Mantei, Scott Williamson) and hope one of them works out. Sure, the Sox ended up getting Schilling, but they were also one of the only teams that could afford him. Same with Damon, Foulke, Renteria, Clement and A-Rod (had the deal happened). So did Theo really perform that much better than anyone else who had such a huge payroll to work with? I don't know. Heading into 2006, the team is in worse shape (both financially and from a talent standpoint) than it was heading into 2005. Doesn't he deserve some semblance of blame for that?

On the flip side, Theo deserves major props for five things:

1. The Nomar-Cabrera trade on July 31, 2004. Few people would have had the testicular fortitude to trade a local icon to save a season; even fewer would have handled it as smoothly when it happened. No matter what happens for the next 40 years, that will always go down as his greatest moment. The Red Sox won the World Series that day.

2. The Big Papi signing before the 2003 season. Like Dan Duquette before him, Theo smartly took fliers on bargain guys who had shown signs of life on other teams -- Ortiz, Williamson, Bellhorn, Mueller, Jeremy Giambi, Jay Payton -- and hoped that some of them would work out. Well, with the exception of Bob Cousy, no "flier" worked out better for a Boston sports team than Big Papi. Theo found him, Big Papi became a cross between Hendu, Gandhi and Paul Revere, and that was that.

3. The Schilling trade and contract extension -- just the sheer perseverance he showed that week. Theo read Schilling perfectly and did everything right.

4. His refusal to deplete Boston's well of prospects during the 2005 season with multiple panic trades -- out of anything, I'm most grateful for this. Not everyone would have been secure enough to avoid kowtowing to the "We got to do something! The sky is falling!" syndrome that starts with the radio shows and newspapers, spreads to the message boards, spills into the ballpark and affects every Red Sox season. The bottom line was that the Red Sox probably weren't repeating as champs with their three most valuable pitchers from 2004 missing (Schilling, Pedro and Foulke). So why mortgage the farm?

5. I have never read one thing about him -- not from a player, a fellow front-office employee or any other baseball executive -- that made me think Theo Epstein was anything but a good guy who honestly just cared about making the Red Sox better.

Of course, it's difficult to separate that last point from an honest evaluation of the guy's performance in Boston. The thing is, he was a good guy -- handsome, local kid, grew up dreaming of running the Sox, said and did all the right things -- and it's easy to overlook some of his mistakes because of the romantic view of the Theo Era. For better or worse, whether he liked it or not, Theo evolved into Boston's version of JFK Jr. When things went wrong, everyone blamed the owners and not him. When things went right, he received most of the credit. You couldn't ask for a cushier situation.

Which raises the lingering question …

Why the hell would Theo leave?

I had a feeling this could happen right after the White Sox series, as soon as I started hearing whispers from semi-connected people back home that the relationship between Theo and minority owner Larry Lucchino was much more complicated than anyone imagined. There were rumors about a squashed Manny trade, as well as some second-guessing from the higher-ups, with the biggest problem being that Lucchino (an infamous attention hog) seemed to be bristling from the attention that Theo was receiving. Don't forget, when this current ownership group bought the team, John Henry and Tom Werner were the money guys, and Lucchino was given a minority stake in return for three things: (1) He would run the day-to-day operations of the franchise; (2) he would handle revamping Fenway Park and derive as much income as possible from the team's revenue sources (the surrounding streets around the park, the team's cable station, advertising inside the park and so on); and (3) he would have a certain amount of control over the team's baseball decisions. In retrospect, Lucchino was a genius -- because Henry was a private man and Tom Werner had been burned by his experience in San Diego, Lucchino convinced them to make him a de facto co-owner (as well as the visible one) without assuming nearly the same financial burden.

So when he watched Theo's stock continue to rise (Lucchino's protégé, by the way), you could see this collision coming a mile away. Put yourself in Theo's shoes -- he wins the World Series and achieves his lifelong dream, he's a demigod in Boston, he's a hot commodity in baseball … and not only is he wildly underpaid, he's still answering to someone who considers himself Theo's mentor, as well as someone who routinely second-guessed and even squashed some of his moves. How was that a good situation? At some point, if you were Theo Epstein, wouldn't you want the car keys? And if you were the Red Sox owners and you had the car keys, as well as a World Series trophy, would you really be that willing to give up final say on every move?

Three weeks ago, I went on Mike Felger's ESPN Radio show in Boston and predicted that Theo would leave. They thought I was crazy. I gave them my whole Car Keys theory as an explanation. They still thought I was crazy. In last week's football picks column, I finally had a chance to write something about it, so I stuck a non-NFL pick in there that looked like this:

Theo Epstein (+11) LARRY LUCCHINO

In the following paragraph, I explained the same Car Keys theory from Felger's show. And as late as Thursday night, it was still in the column. But before I sent it in to my editors, I checked Friday's Boston Globe (which comes online around midnight) to make sure there was nothing about Theo's situation in there. Just my luck, there was a story about how Theo's contract was in the process of getting done. Oh, well. I yanked the section. And there's a reason I'm telling you this -- Theo's "surprise" departure didn't come out of left field (as so many people seem to think), and it certainly wasn't difficult to anticipate or predict. Just eight years ago, a similar power struggle unfolded between Patriots owner Robert Kraft and Bill Parcells, and that ended infinitely worse than this one. In the case of Theo-Lucchino, the writing was on the wall. One guy loves going on radio and TV shows, the other guy hated it. One guy loves the power rush of running a team, the other guy just liked making baseball moves. One guy loved getting credit, the other guy didn't care. But both guys wanted the car keys. And there was no way this could ever be truly resolved without one of them leaving.

Here's what I love about Theo (and why his stock rose with me for life): Not everyone would have the stones to walk away from their dream job. Putting myself in his shoes, my dream job would be running the Boston Celtics … and I'm pretty sure I could have done better than some of the bozos of the last 15 years. If I spent my entire life working towards that chance, and then I got it, only one scenario would make me give that up -- if I couldn't stand working for my owners and felt like they were constantly second-guessing and undermining me, and the situation deteriorated to the point that my quality of life was being compromised. Even then, I'm not sure I would walk away.

Well, Theo walked away.

When Dan Shaughnessy published his hideous mentor-protégé column in Sunday's Boston Globe -- a column covered in Lucchino's fingerprints that made Theo come off like an ungrateful, disloyal, incompetent jerk -- Theo decided to change his mind about staying with the team. How could he work for people that he didn't trust, people who would wait until both sides had agreed to terms before leaking a "Now take this!" column that was clearly meant to put him in his place. Imagine being Theo, waking up on a Sunday morning and seeing that slanted crap in your local paper -- a house organ with ownership ties to the Red Sox, no less? How could you come back to the team and live with yourself? They underestimated his character, his resolve and his willingness to walk away from the only job he ever wanted. At least he left with his dignity.

(And just for the record, I don't believe any of this "Boston was too crazy, he wanted a normal life again" stuff that some people are theorizing, including our own Peter Gammons. That seems like one of those "It's not you, it's me" rationalizations that you would make up when you dump your overbearing girlfriend. What was Theo supposed to do, burn his bridges on the way out and say what obviously happened -- that his former mentor, as well as the two other owners who gave him a chance, basically drove him crazy enough to walk away from his dream job? The truth will come out. That's all I'm saying. There have been whispers about major problems with the Lucchino-Epstein relationship for far too long. Just wait.)

As for the Red Sox, they have shamed themselves beyond belief, with the Shaughnessy column being the final straw. The same guys who brought Boston a World Series also formed an Orwellian media conglomerate in which they control all the information in the city's most important newspaper, as well as the TV and radio stations that carry the games. Just about every Red Sox-related scoop is directed to one of those three outlets, with Boston Herald writers repeatedly complaining about the unfairness of it all. In particular, the Epstein coverage was appallingly one-sided from the Globe's side -- culminating in Shaughnessy's incredible column, to the point that Red Sox fans have to question the credibility of anything they read in what used to be a sports section that meant something. It was telling that, on the same day that Theo announced his resignation, Monday's Globe contained a story reporting that he had signed for three years.

Call me crazy, but I believe this is a bigger story than Theo Epstein leaving the Red Sox -- an unprecedented situation where a sports franchise controls the local coverage of itself, to some degree, in every possible medium. During the A-Rod debacle in the winter of 2003 -- when Lucchino clashed with Texas Rangers owner Tom Hicks to the point that John Henry had to remove Lucchino from the trade talks and the Red Sox took a "Screw Hicks, we'll wait until the price tag drops in spring training" position, never imagining that the Yankees could get involved -- Lucchino received a curious amount of leeway from a local media that normally jumps on that stuff (including from the routinely vicious "Dennis and Callahan" show, where Lucchino has a weekly segment). Over these past few weeks, when the team was clearly lowballing Theo financially and acting like he was expendable to a degree, only the Boston Herald and Providence Journal were critical. More than anything else, I think that skewed situation led to young Theo fleeing the coop.

There's one other factor here, and I guarantee it's playing a bigger role than just about anyone can understand …

When you dream about doing something for a long time, and then it happens, it's never actually as good as you think it would be. There's almost a surreal letdown of sorts after the fact. And it's impossible to explain unless it's happened to you. For instance, ever since I was in college, I dreamed of having my own sports column and covering a Boston team when they won a championship. That's all I wanted. In the spring of 2001, ESPN found me. Nine months later, my beloved Patriots went to the Super Bowl and shocked the Rams in New Orleans. I wrote about it every day, and on the morning after they won, my column ran on the front page of this Web site. Greatest professional moment of my life, right?

Well, something weird happened. After that game, I couldn't stop thinking, "All right, what happens now? What do I do? How can I top my dream moment?"

And the thing is, you can't. The moment happens, it ends, you celebrate and feel good about yourself … and then it's on to the next day, and you have to figure out what the next challenge is, and deep down, you're wondering why you didn't enjoy that watershed moment more than you thought you would. I don't know Theo, I have never met him, and the experience of being the general manager of the first Red Sox championship in 86 years was roughly 100,000,000 times more profound and important than my experience in New Orleans. But the fact remains, after that Super Bowl column, I struggled writing this column for the next seven to eight months; eventually, I ended up moving to California to write for a fledgling late-night television show. That Super Bowl trip changed everything for me.

Did something similar happen to Theo after winning the World Series? Is this what happened to David Caruso when he said, "Screw it, I don't need 'NYPD Blue' anymore?" On a much, much larger scale, is this what happened to talents like Dave Chappelle, Eddie Murphy, Kurt Cobain, Michael Jordan and everyone else who either walked away from their alleged dream job or sabotaged it in their prime? Is that why the Peggy Lee song "Is that all there is?" rings especially true in moments like these?

Right now, I don't have an answer for you. But since I failed to get my previous "car keys" prediction down on paper, allow me to make another one for you: I see Theo taking the year off. I see him going into relative hiding, growing some sort of goofy facial hair like a fu manchu, maybe even growing his flattop out. I see him refusing just about every interview, laying low, maybe doing some consultant work for Josh Byrnes in Arizona. I see him moving out of the city to salvage what's left of his privacy. Hell, he may even have a crappy music album in him.

And a year from now, maybe two, he'll come back to baseball refreshed and recharged, armed with enough savvy to avoid another front-office quagmire like the one in Boston. Maybe it won't be his dream job, but that's the thing about dreams -- sometimes they come true, and sometimes you have to deal with the consequences and figure out what's really important to you.

Something tells me that Theo hasn't figured this out yet. I hope he does. Overrated or not, he still goes down as the guy who brought the Red Sox their first World Series title in 86 years. And after something that monumental, maybe you need a couple of years to come up with the right encore. To be continued.

Bill Simmons is a columnist for Page 2 and ESPN The Magazine and his Sports Guy's World site is updated every day Monday through Friday. His new book "Now I Can Die In Peace" is available right now on and in bookstores everywhere.