If I had the choice of which guy to go grab a beer with — Tony Romo or Jay Cutler — I am picking Romo every time.

But now that Cutler is stepping away from playing and will accept a role as a game announcer with Fox, if you’re asking me who might make the better NFL analyst next season, I think I am taking Cutler.

I don’t know the man at all. I’ve had exactly one mano a mano conversation with the guy over the years, and it lasted all of about one fairly awkward minute. Cutler never struck me as the type to chew the cud with media members, but perhaps I am wrong. What he is, however, is smart, articulate and direct. Ask Cutler a good question and he almost certainly will give you a good answer. This will help make him a good analyst, I believe, despite everything you think he is as a person.

Cutler’s reputation of being the aloof eye-roller toward the media and as a locker-room cancer whom most of the Chicago Bears players hated, I’ve been told, are not entirely accurate portrayals of him. I’ve talked to media members who have covered the Bears on a daily basis over the past few years, and I’ve always been surprised at how they generally like him and find him to be helpful and often surprisingly earnest. And Cutler has had some teammates who like him and find him to be a very straight shooter, but also a fair one, behind the scenes.

Romo is one of the nicest guys you’ll ever meet in this league. It doesn’t require much sleuthing to figure that out. Years ago I was a presenter at the Ed Block Courage Awards for my previous job, and I was covering the NFC East at the time. I went up to Romo during a break in the festivities, introduced myself and had a really enjoyable chat. He was charming, funny, looked you in the eye and handled conversation easily while a throng of autograph-seekers approached him during it. I was impressed very much at how he handled himself.

I asked Romo if I could get him on the record later after the event for one story I was working on about his contract at the time, and he said absolutely he’d help. However, as soon as the chatter moved from friendly, off-the-record stuff, Romo went into guarded news-conference mode like he’d flipped a switch. It wasn’t bad, mind you, and Romo is respectful of the job we do as media. He gets it; he knows we have to ask certain things, and he thoughtfully answered questions as best he could. But I also found him to not want to say the wrong thing and that he often spoke in generalities, with the easygoing smile that was on his face when we chatted turned to this very serious game face that made him … frankly a tad boring. It’s the kind of thing CBS will have to work out of him, and there might be no better point guard in the business to help do so than Jim Nantz.

But right now, I think Cutler will have a more seamless transition into his role. He also will have a great teammate in Kevin Burkhardt, a pro’s pro who handled about as wild a trio during his baseball coverage alongside Pete Rose, Alex Rodriguez and Frank Thomas (do yourself a favor and read this terrific feature on that group by Big League Stew’s Mike Oz from last October) and did so with aplomb.

To me, Burkhardt will find Cutler very easy to work with. Cutler is a smart guy, he thinks fast and can give thoughtful, pointed answers in a flash. I still remember the time I went to one of Cutler’s midweek news conferences when I was doing some work on the Minnesota Vikings, and I could tell he knew exactly what I was going to ask six words into my question. And of course, Cutler had figured out his answer by the time I was done blabbing.

Cutler also is a little weird, a little funny and a little … unexpected. This 4-plus minutes is well worth your time, trust us:

Both Cutler and Romo have the potential to be very good in time. They’re both smart, analytical and comfortable in front of the camera. Each will be working with good people beside them. But I just think Romo might be a bit too nice to offer truly pointed criticism whereas that shouldn’t be an issue with Cutler.

Look, Jay is Jay. You’ve likely heard he thinks he’s the smartest guy in the room, right? Others think so, too.

Dan Wiederer has covered Cutler the past few seasons. His Twitter timeline is a good place to start to get an accurate idea of how Cutler operates. I’ve always been fascinated by Cutler because over time I do think he has softened a bit. Our own Frank Schwab covered him for his first three seasons with the Denver Broncos. Cutler wasn’t the easiest guy to work with back then.

But I think over time we’ve seen a bit of a different person, and being a little bit removed from the NFL’s inner circle and perhaps not especially close to a lot of players might not be a bad thing for Cutler as he gets set to critique their work on a weekly basis. Romo doesn’t figure to be the next Jon Gruden — the man who ebulliently loves everything and everyone — but could be a bit gun-shy about calling someone out on national TV.

You think Cutler is worried about that?

Romo felt very insecure about his decision in the aftermath of retiring. The whole thing felt a bit rushed and awkward. In his conference call with the media to talk about his new position, I found Romo to be a bit conflicted and ambivalent. He was more open and excited when he spoke the following day, but there’s still a part of me that thinks he isn’t sure he made the right move or that he can be great at his new analyst job.

Meanwhile, Cutler also admitted that he’s between his feelings a bit in what I found to be a very disarmingly honest statement this morning, but it also feels like he’s the type of guy who can move onto the next phase of his life more easily and embrace a new role and be naturally good at it. With Romo, it might be a little less natural and perhaps a bit more work for him at first.

Who knows where they’ll each be in three or four years. Maybe either Romo or Cutler decides this media thing isn’t for them. Maybe they both end up great at it. But my gut tells me that Cutler will surprise people with how good he is right away. I thought Chris Webber would be terrible at calling basketball games, and yet for the most part he’s fantastic. Romo might be a bit too Grant Hill for my liking, although Hill over time has become decent, if not a bit vanilla and unoffensive.

You worried about Cutler being able to take a shot or two and be comfortable doing it? I’m not. You watch: This will be a good fit. One that might surprise you with how seamless it is.

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Eric Edholm is a writer for Shutdown Corner on Yahoo Sports. Have a tip? Email him at edholm@yahoo-inc.com or follow him on Twitter!

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