#2 Piper's Pit
Bobby's greatest moment as a manager, came in early 1987 on Piper's Pit when he revealed to Hulk Hogan and the world who his new signing was. Hogan's best friend, Andre The Giant!
Andre was beloved by the fans and his heel turn shocked the business to its core, helping to build Wrestlemania III to become the biggest event in history.
While Andre and Hogan played their parts to perfection on The Pit segment, it was Heenan who stole the show. While smug and cocky at his new acquisition, there was a layer of truth in his words, that Hogan had held talent down and they were tired of it.
This could perhaps be seen as the first WWF example of a "worked shoot", with Heenan telling fans in a coded way what many felt backstage.
While Andre lost at Wrestlemania, Heenan arguably had the last laugh, seeing The Giant take the WWF title from Hogan less than a year later. This remains one of the best executed heel turns in history, and it's in no small part to the excellent work done by Bobby Heenan to sell Andre's frustration.