Cashing in on Some Mad Men Season Five Bets

As has been the case a couple times in the last few months, we’re in All Mad Men Monday mode. If that doesn’t interest you, see ya later this week, no hard feelings. But after what was another super exceptional season of TV’s best show, I can’t help but break down some of the prop bets from before the start of the year and see where we made some money.

There are also HUGE SPOILERS in here, so don’t read this if you haven’t watched Sunday’s season finale or if you have anything to catch up on for this past season:

to all the dads of new york city women circa 1966 -- i feel for ya.


Easy money, baby. Not only did they bang out one of these nice and early — where we set the stage for Don’s hallucinations when he’s drugged up Tommy Gavin-style — but then they added another in last night’s finale just to insult the people who didn’t think it would happen once. It makes total sense that he’s sick all the time. He smokes three packs a day, he drinks like a fish, he’s got a high-stress job and a taxing homelife … he’s lucky it’s only a toothache! Shouldn’t he have had like four heart attacks by now? And yet, even when he’s sick, we get an extra-special look into the psyche of what makes Don Draper tick. We find out he’s not a complete dick to women because he’s just a dick. In reality, he keeps them down, embarrasses them and demeaningly makes it rain up in his office because otherwise, he’s afraid he’s going to lose them. So he’s not a complete jerk, just a really, really effed-up-in-the-head guy scared of abandonment, likely because of his abandonment as a child. The answer to the question, “Are you alone?” is “It doesn’t matter.” In that moment, at least, it doesn’t matter. Don may be able to resist cheating on his wife once, maybe even twice. But now that he knows he’s set Megan on a path of success, he’s convinced himself that she’s leaving him at some point. So he’s going to do what he can do to destroy his relationship himself instead of waiting for her to do it for him. New York City dads of the 1960s, lock up your daughters.

can't believe it took four years for someone to knock him out. but now that it's happened three times, all is right with the world

NUMBER OF PEOPLE WHO WILL KNOCK PETE’S TEETH IN? (Over/under 2.5, +200 on the over). Winner: 3

Sucker bet alert! If you wanted to go with the under, you worked under the theory that there hasn’t been one real fight in four years of the show, how could it happen three times in one season? To one guy? But here was my theory: Sniveling, pathetic Pete meets between six to 10 people a day who want to punch him square in the face, right? So you shouldn’t be asking, “Why would it happen?” you should be saying, “Why hasn’t it happened yet?” The law of averages was bound to catch up with him at some point. And how ’bout the way it covered! We got rid of the first butt-kicking with Lane about six episodes ago, so you had to think you were in good shape if you took the over. But with only about 20 minutes left to go in the finale, we were still two short. Then his train partner gives him a fat lip, so as you’re thinking, “OK, we got a shot at this, maybe Trudy will find out about the little tryst and sock him … wait, WHOA! AND WE’RE WINNERS!” just like that. File it under “great moments in gambling.” Although you’d really, really be rolling in it if you were ballsy enough to bet on two of them being senior citizens (+1350, it would have had to have been).

no more of this with megan gone. but least he didn't cheat on her. yet.

NUMBER OF PEOPLE WHO WILL CHEAT ON THEIR SPOUSE/GIRLFRIEND? (Over/under 3, -140 on the over). Winner: 4 (at least)

You wouldn’t have made much money on the over, but how could you not take it? Let’s see here. We had Pete and Rory Gilmore (twice), Roger and Megan’s ma-ma (twice), Lane sticking his tongue down Joan’s throat, Harry and that Hare Krishna lady … who am I missing? I’m not even counting Joan whoring herself out since it’s pretty obvious she wants no part of her d-bag Army husband, even though they’re still technically married. I know I missed a couple. You can’t make this line high enough for me next year with Roger single and Don likely back in the saddle.

WILL ANYONE IMPORTANT LEAVE THE FIRM? (Even money) Winner: Yes (three)

More easy money. The staff at the firm had been pretty stable last season, so you had to see some kind of storm coming. Megan bolted, Peggy shook Don off her leg like the 4-year-old asking his mommy to stay that he was and Lane offed himself last week. Not too shabby. I’m already saving money to bet on “WILL PEGGY COME BACK TO THE FIRM?” next year and I will vote in the affirmative. You can only find life on the road with stray dogs humping outside your motel room window glamorous for so long.

don't care.

NUMBER OF TRULY GREAT EPISODES? (Escalating odds for each episode) Winner: 12 of 13, +900

Boy, you’re cashing in if you saw this coming. Up until last night, Mad Men gave us one of, if not the, most impressive seasons it’s had in its five years. It’s been fantastic, even by Mad Men standards. By something like CSI: Miami standards, it’s been the bestest show that ever was and ever will be. Every episode was incredible, and it gave us no less than two top 5 episodes — the Roger LSD trip/Don-Megan trip/Peggy extortion episode and the Joan the Prostitute one. They both might be two of the top three episodes of the show’s history, up there with the Gypsy and the Hobo from season three. And there wasn’t much drop-off in any episode this season — that is until we got to yesterday’s finale. Or as I like to call it, “Crap I Didn’t Give a Crap About.” Pete and the Gilmore Girl? Megan and her ma-ma? Don with a toothache? What happened, they couldn’t figure out a way to stuff Freddy the Pants Wetter into this one? There was only one truly Mad-Men-type-funny line (Trudy: “What’s wrong, did you get in a car crash again?” which apparently was Pete’s cover for when Lane effed him up with his British fists of fury), Don was laid up and weak and boring, Roger was frustratingly following a familiar path and there was no Fat Betty to make fun of. At one point during Pete’s little emotional spewing to Rory I actually screamed, “What the heck is going on here???” My wife came up with the best explanation. It was like the season 6 finale of Rescue Me that I was convinced at the time and remain convinced now wasn’t supposed to be the finale. Like, Mad Men lost count of the episodes for the year or something. Until the last five minutes, at least, when we got a couple hints into what the major themes of next year will be — Sterling Cooper Draper Pryce‘s expansion, Megan’s burgeoning acting career and Don’s inner demons. In other words, back to the good stuff. SEASON GRADE: A. FINALE GRADE: C+

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