An Open Letter To Theo and Ben

Dearest Theo and Ben,

Finally, you're both sitting on top of the world. Theo, the president. Ben, the general manager.

Sure, you're in different places now, but I can't help but wonder if you two talked about this day, not just over the last few weeks when it became inevitable, but years ago. Surely, many years back in the hallowed basements of Fenway, this would have seemed a pipe dream.

Now, though, it's a reality, and you probably even spoke by phone after your respective press conferences this week to gossip like teenagers over who asked the worst questions and which female reporter in the front row was dressed the best, making it difficult to focus.

I'm not writing you guys to discuss the finer points of your media debuts in your new roles, though I'll touch on those briefly. I just thought, with so much history and the uncertain futures ahead, something had to be said.

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Theo, you spoke a number of times – in print, interviews and your press-conference-disguised-group-hug – about Bill Walsh's theory concerning staying in one city as an executive for too long. Admittedly, you had me interested until Mike Felger proved it 'bunk' on "Felger and Mazz" moments later, citing Walsh's regret over leaving San Francisco until the day he died.

Listen, you could have just said, "Times change, people change…I needed a change of scenery…I wanted a new challenge…I couldn't resist the promotion…I gots the powah!...Cha-Ching, where my hoes at?!" – Anything, really, and we would have understood. But, there was no need to dance, especially when you knew you weren't possibly going to face one tough question at that tickle-fest in Chicago. I've seen more ruthless mock press conferences in elementary schools…and I'm still recovering.

Honestly, you may as well have compared your tenure to the TV show "Friends."

"We had a good run, but the storylines were getting old and it was just time to move on to a new role, a new character. We all knew Joey and Chandler wouldn't live together forever. And, seriously, how much longer were they going to drag out the Ross and Rachel thing? So, this is my 'Theo' spin-off, but I chose the Windy City instead of California, and I hope I do better than Matt LeBlanc. You guys wanna hear about me in the basement with the red stapler again??"

There. A few smiles, an Office Space reference, a few high-fives and you move on. Who needs an hour? To paraphrase Vince Vaughn in Old School, "Theo, we know you want to win a World Series in Chicago. I think everyone in baseball knows you want to win a World Series in Chicago. I'm trying to ask our friends in Boston if they care about you winning a World Series in Chicago."

Can we talk for a moment, too, about those pictures you posed for in front of the ivy at Wrigley? I swear, man, you could be a Kennedy, you know, without the alcohol abuse, the cheating and some of that other garbage. Point is, you're a good-looking fella and I don't mind admitting it. If you were an actor or a rock-star, those pictures would be pin-up posters in a 15-year-old girl's bedroom.

Here's the thing that gets me, though. You're smooth, well-spoken, come from a background in writing and public relations, and you certainly had more than enough time to think about and prepare for your press conference. So, Theo, why the script? I felt like I was watching a White House correspondent. Your speech, while well-written, was dry, repetitive, and monotonous, and you looked like you had emotionless, dead eyes. The Cubs are paying up more than $18 million. I'm sure an intern could have found a teleprompter somewhere, or least someone to hold up giant cue cards.

My only theory here is that there's a bit of regret. Maybe that's from leaving the team you lived and died by as a boy, or maybe it's simply the timing of the cataclysmic ending, followed by a red carpet entrance in Chicago. If it's ego and you don't want to be remembered for your exit, but rather for your two titles, six playoff appearances and 800+ wins as GM, I get it, you deserve it, and the next time (first time) we grab drinks, they're on me.

What I wanted from you, Theo – if we fans had to see you go – was genuine excitement and perhaps more of an explanation, even if it really wasn't a mystery. You should have been smiling ear-to-ear, much the same way that Larry Lucchino was now that you're gone.

Ben, you stepped up to the metaphorical plate. I don't remember Theo's introductory press conference nearly a decade ago in Boston, but I'm quite certain you killed it.

You spoke from the heart, you didn't need a script and you've got the highly-coveted Peter Gammons stamp of approval. As many have written, including our own Dan Roche, you were confident, direct, loyal, funny and truly likable. Aside from the fact that I could close my eyes and basically hear Theo with each turn of phrase and the general pattern of your speech, you brought it, and I can see why you got that concert-like introduction.

Listen: Ben Cherington On Felger & Mazz

Seriously, though? Maybe it's just my memory failing me again, but I sure can't remember someone being introduced in a setting such as that being met with a round of applause. Watching on TV, I felt like it was a late night talk show and the applause sign flashed. At first I thought it was lame, and I still think a bit cheesy, but you should be proud of it. They like you…they really like you!

People quickly forget that Theo wasn't the first choice as Sox GM oh so many years ago, though the release of Moneyball has reminded the masses. At the time, he was just a kid – a kid that never played the game at a high level, thought perhaps at one point that he'd be a lawyer, wrote for his school newspaper and worked in PR until the right people took a liking to him.

Maybe in some ways Theo was that guy for you, the right person taking a liking to you and grooming you for this position. You know your differences – you played the game in high school and college, you worked your way up the ladder in the scouting department, you've got a genuine feel for the game without the need for a computer, and you've even got a few weeks as interim GM under your belt, during which time you executed a deal that directly impacted Boston's success in 2007. Plus, as you said, you don't have a gorilla suit, nor have you ever practiced strumming Dave Matthews songs on a guitar.

Toucher & Rich: Is It Theo Or Ben?

That's all a long-winded way of saying, you're far more qualified for this job now than when Theo ascended to the post several years ago, and that should be noted. Sure, we'll miss Theo for what he did as a relative unknown, but I think I speak for the masses when I say we now welcome you with open arms for what we believe you will do in the future. This team doesn't need a savior, but it does need some help, and I believe in your ability to do the job.

By the way, Ben, kudos for dropping an absolute bomb on your first day on the job. Nothing will get you more pats on the back than revealing John Lackey won't be taking the mound in 2012. In a world of 'what have you done for me lately,' you made me one happy man for at least a few hours. Frankly, that announcement should have caused the applause sign to light up again…longer, and multiple times. Then, at the close of the conference, you should have been carried out of there like a king on his portable wooden thrown. I bet many members of the press would have volunteered to lift each side. Even John Henry and Tom Werner could have jumped in…you know, had they been there. Let's not get into that – I don't want to dampen your moment.

Now, guys, you get to work together to determine Theo's worth as you work out compensation for his early exit. Oh to be a fly on the wall for those talks. Normally you'd probably be on speaker phones in boardrooms, but you two are likely just goofing around on your cells in your kitchens while you make dinner and try to quiet the dogs with a chew toy. It makes me think of when I was a kid, trading cards with my neighbor down the street after school. You'll have a few laughs, make a trade, and go back to watching "Boy Meets World." Good luck, have fun and, remember, we just don't really care anymore, so get it over with before the Commish has to step in.

So, in closing…Ben, you've got your work cut out for you in terms of finding the right manager and the right mix of personalities in the clubhouse, but you're smart, you've got talent in there, more money to play with than Justin's Bieber and Timberlake combined and a fan-base that will never abandon you – despite the continued threats.

Theo, hats off to you. Anyone could have pulled a Phil Jackson here and waited around for the right opportunity, the right number of superstars and coasted to a championship or 10. You're taking over a team so bad, it blames its struggles on a goat and a nerdy-looking dude named after a Simpsons character. It's sad to see you move on, but we thank you and we're rooting for you…unless Ben's boys see you in October.

Hugs and kisses,

Adam

Adam Kaufman, a native of Massachusetts, joined the Sports Hub as an on-air personality in June 2011. He has worked as a television and radio anchor and broadcaster for various outlets since 2004, and his written views on sports and entertainment have appeared on NESN.com and in the New England Hockey Journal. You can follow him on Twitter @AdamMKaufman.