'Mad Men' midseason 2014 finale: Bert Cooper meets his 'Waterloo'

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We're at the end of "Mad Men" for 2014 tonight, fans. The halfway point of the final season is here, and as promised, they're splitting the final season. So you'll be messing up what year it is when we next see a new episode.

But on tonight's (May 25) midseason finale, it is July 1969, humans are landing on the moon, and we learn who meets their "Waterloo."

The Moon Landing

Perhaps the biggest moment of the show since JFK's assassination has come and everyone is watching Neil Armstrong set foot on to the moon surface. I break this out because we panned to every character watching and it's a momentous occasion. There's a sense of wonder with everyone, from Roger's grandson on his lap to Sally looking at the stars to even Don, who actually takes a moment to recognize something going on in the greater universe, and is amazed. It's a far cry from when JFK was killed in Season 3 and Don was perplexed as to why people were so upset.  

But before we get to Don tonight, we visit ...

Bert

Minutes after the moon landing, Bert Cooper passes away. Quirky and sharp, we take off our shoes in salute. How fitting he should die after uttering "bravo." A second father to Roger and the glue of all the various incarnations of Sterling Cooper, Bert always had a good line, a clever zinger from his king-like vantage point. But the times, they are a'changing.

Don 

"You're just a bully and a drunk ... a football player in a suit." -- Jim

Last week, Don and Peggy reconnected over the Burger Chef campaign, circling back to each in their orbits. Since both of them have been struggling this season, watching them slowly dance to Sinatra's "My Way" while reassuring each other that they're both fine (or going to be fine) was touchingly poignant. In many ways, they truly are equals now, even if Don is going to take the lead on the Burger Chef pitch.

Or not. 

Because Jim is firing Don for breach of contract. He broke his re-hiring addendum by crashing the Philip Morris meeting, and that business isn't happening. In an impromptu hallway meeting, the rest of the partners find out about Jim's letter to Don. He did it without their knowledge, and none of them are happy about it. It's Joan, who actually agreed with Jim's letter and letting Don go, who warns Jim that he shouldn't have done that. 

Don is tired of fighting, and he realizes this could be the best time to leave the agency. When talking it over with Megan, explaining this firing would free him up to move to L.A., she is silent. 

And that silence speaks volumes, as they both understand that pause to be the death knell of their marriage. Don says he'll take care of her, but she turns that down. The setting for this bi-coastal telephone discussion -- Don in a dark, twilight-lit New York bedroom vs. Megan sunning herself outdoors in beautiful L.A. -- is poignant.

But Burger Chef is still on, and without Megan to run to, Don is staying and fighting. However, as Roger points out, the hallway vote no longer applies -- without Bert, Don no longer has the votes to overturn his firing. He tells Peggy she needs to do the pitch because if he wins the business, and is then fired, the new account could be in jeopardy.

Peggy

"Every great ad tells a story. Here to tell that story is ... Peggy Olson." -- Don

Peggy is 30. The big 3-0 came and went without so much as a vase of flowers. But she does have a cute contractor working on her building and Julio the neighbor kid, who she's actually grown fond of in a pseudo-foster kid way, even if he is moving to Newark. Another person is leaving Peggy. 

And even Don is leaving Peggy. By handing over the Burger Chef pitch reins to her due to the politics at hand, Don is both leaving her, and giving her freedom and his trust at the same time. She may be 30, but she's finally a grown up now. She beautifully wraps the moon landing into her vision of a television-free "Family Supper at Burger Chef," winning them over easily. 

Sally

Betty's college friend Carolyn (Kellie Martin, of "Life Goes On" fame) is visiting with her teenage sons Neil and Sean. Oh, the summer teenage fling story! But not with the one you would think (Sean, the buff one.) No, Sally, the sly girl, instead kisses the geeky Neil after he teaches her how to use a telescope. You're smart, Sally Draper.

Roger

"We got an offer from McCann Erickson to buy the agency. Hear me out." -- Roger

Roger is incredibly angry over Jim's firing of Don, and looking for reinforcements. And Jim isn't backing down, even taking advantage of Bert's passing to say they can do a two-for-one call to the clients, informing them of Cooper's death while telling them Don has been fired. But Bert's passing actually means Roger is all grown up now too, just like Peggy.


Only hours after Cooper's death and minutes before the Burger Chef pitch, Roger play his full hand with Jim Hobart. He shores up everyone's future (including Don's) in the agency by offering it up, lock, stock and barrel, to McCann Erickson. Why not get the whole agency instead of just a few people and one account, he says? Hobart agrees.

When Don gets back to New York, Roger tells him first about the offer. Sterling Cooper would be a subsidiary, with Roger as the president, and Don as the real, returning creative director. It just depends on ... 

Ted

"Lane Pryce." -- Pete, referring to Ted

Hey, remember Ted? Moving to California didn't solve his problems and he wants out of advertising entirely. He won Chevy, but lost Peggy, and his edge. But since the McCann Erickson deal hinges on securing Ted coming along with them, it all comes down to sourpuss Ted.

In his suavest and most skilled move ever, Roger tells the partners (and no, Harry isn't actually a partner yet POOR HARRY) about the offer, explaining that they're about to become multi-millionaires, with the exception of Jim, who isn't part of the plan. They just need to sign a five-year contract. But Ted still wants out.

Until Don explains that he may think he wants out, but after being "out" himself, Ted really doesn't. He can, instead, go back to just being a creative director -- no clients and stock prices, no politics. Just working. 

He's in. And Burger Chef is in. They've won the new business, agreed to be consumed by McCann Erickson (and become incredibly wealthy -- Joan's Cheshire cat grin was stupendous,) and are able to bury Bert Cooper with dignity.

And then things go weird. While being eulogized by Roger upstairs, Bert Cooper appears to Don in a musical sequence. No, really. 

Yes, Robert Morse did indeed win a Tony in 1962, and he belts out "The Best Things in Life Are Free" to Don, along with secretarial backup dancers.

No, really. 

Is it Ted who has lost his mind? Or Don? It's really no matter. It was an amazing send-off for Bert, regardless of Don's sanity. But it leaves this midseason finale with a particular earworm: The best things in life are free? Did Don win this battle or lose his own "Waterloo" as well?

We won't know for a few months. 
Photo/Video credit: AMC