Friends and colleagues of pres & CEO, Bloomberg L.P. Dan Doctoroff, this year’s recipient of the Frank Stanton Award for Excellence in Communications, roasted the media exec at a Center for Communications luncheon in NYC Mon. Shots were fired at topics like losing the Olympics bid, Bloomberg Terminal’s outdated interface and Doctoroff’s tendency to take credit for other people’s ideas.

Some other things we learned about the honoree: “He isn’t just compulsive, he’s incredibly competitive,” said sr advisor, Related Companies, Jay Kriegel. And nothing gets him betting like the sport of dieting—an activity which inspires “diet face-offs” and “mild attacks on staff” if he’s fully engaged.

By all accounts, he’s reached “media mogul” status. One roaster revealed an unlikely love affair. Dealbook editor and co-anchor of CNBC’s “Squawk Box” Andrew Sorkin said Doctoroff and he had met on JDate years ago, when the big boss was courting him. “We flirted for quite a while,” but ultimately the “’Brokeback Mountain’ thing ended." He added longingly that Doctoroff “may have been the one that got away.” Sorkin praised Bloomberg for its transformation into a media conglomerate. “As a competitor, we’re going to have to start calling you a media mogul,” he said.

Andrew Lack, CEO, Bloomberg Media Group seconded the honoree’s “media mogul” status, but not without some careful thought. “Is he? Yes. He’s Jewish. He’s Rich.” He’s also “the smartest guy in the room,” but that’s really just a function of the room, he added quickly. “Television is the last refuge for the C-student.” Does he have the ego of a media mogul? You bet. “He’s right up there with the best of them,” Lack confirmed.

After the roasting Doctoroff thanked his colleagues, saying that there’s “no greater honor to be cruelly ridiculed” by them. He then brought his own Bloomberg Terminal on stage and launched a faux service called “Bloomberg Media.” Among other things, it featured a “media mogul tracker” (indicated by the location of yachts on a map) and a service called “Who’s gunning for your job?”

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