I think Connie is that big of a deal and Bert has $'s in his eyes. I lost all respect for him after that conversation...

Bert didn't get to be half of SC by being Mr Nice Guy. He is a hardheaded businessman and Hilton was HUGE at that time. It wasn't like now where we have multiple international hotel chains. Hilton was an original and had a reputation for quality. The majority of business travelers used it. SC was only getting the NY Hiltons, but it was a foot in the door to the rest of the chain.

I don't think Bert is particularly fond of Don personally. He appreciates Don's talent and money making capacity. I don't think Bert is particularly fond of anyone, really.
Did you notice the look between Roger and the Brit when Bert remarked that Conrad Hilton was a bit of an eccentric? I laughed out loud.

Bert's an eccentric guy (it was hilarious to hear him call Connie that, definitely a case of a pot and a kettle). However, he is also a very pragmatic business man. He is totally right about how he has nurtured Don's talent and stuck up for him. I think Burt respects Don, but he will do what he has to to keep Don around and please a whale of a client. Besides, Don owes it to SC to sign that contract when he knows that he plans on sticking around SC, even if he hates the idea of being fenced in. So Burt called his bluff and showed him that he will play his dirty blackmail card if need be. Don owes Burt, no matter how bitter he may be about it - Burt kept Don around after he found out about Don's secrets, and he used that knowledge when he had to. I respected Burt more after that. He's no clueless goofball in the corner office; he'll go head to head with Don Draper and win.

I think Roger and Bert are terrified that Don could go anywhere he wanted...even cross over to Hilton and work exclusively for Conrad. He could yank that account and leave SC without a brilliant creative director. Don had already built an amazing track record before Pete told Bert about "Dick Whitman". Roger's last (and pitiful) resort to get Don to sign the contract was to call Betty, but Bert pulled a dishonorable stunt, IMO, by shaking Don down for that signature.
When he learned about Don's "secret" he acted the utmost of gentlemen while putting Pete in his place. Now, Bert is no better than Pete on that score. He also knew what a gem he had in Don when he made him a partner, gave him bonuses and bought him the Caddie.
I'm curious though. Even though Roger was an idiot for calling Betty, is Don really angry with Roger for being Bert's henchman?

And yet Burt sacrificed so much power and control in the Brit deal...During the negotiations Sister Alice was suggesting this meant the beginning of his pulling out to enjoy his cows, etc. Why suddenly this powerplay squeeze on Don? Could it be that Burt is concerned about Roger here? Roger's got no credibility with the Brits according to dear ole Guy's chart and Don is their "face of Sterling Cooper". If Don goes both Roger and Burt would have very little leverage with the Brits.

Then too this may be Burt's way of telling Don "I've indulged you enough, it's time to grow up, cowboy." It just seems strange he should suddenly pull this. Though of course he may have taken Don's threat to walk which spelled the end of El Presidente Duck a bit harder than Don realized and vowed to get tougher with him next time.

Hooray for Bert, the silent philosopher type, he walks softly and keeps his cards to his chest, but when he needed to be bold he stepped up!

Great comments everyone. At first I wasn't going to click on this topic because I thought it might be the continuation of someone saying that Bert was Don's father or something equally out there. Boy am I glad I did not miss your fabulous insights here.

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