During the 1980s, Dileo was the portly man standing next to Micahel with the cigar, gruff voice, and ponytail. Without Dileo, Jackson's storied career would not have been what it was. It was Dileo who suggested that Jackson release Beat it while Billie Jean sat at Number 1. As a result, Jackson had two songs sitting on top of the charts at the same time. Dileo also served as the reclusive singer's mouthpiece, often speaking for him at press conferences and interviews.
I've always respected Dileo because from what I've read, he was not a "yes" man. He told Michael the truth, no matter how much it hurt. The "official" reasons for Michael firing him is because Bad did not outsell Thriller, and because the Moonwalker film was not shown in theaters in the United States. I've heard that the private truth of the matter is that Dileo warned Jackson to stay away from children. Well, you can't tell Michael Jackson what to do, so Dileo was abruptly dismissed. Had Michael listened to Dileo and took his advice, the child allegations would not have happened. But again, I don't know if this is the official truth. There's a lot of theories out there. However, it's no coincidence that Jackson's career began to slowly fall apart after Dileo's departure. Michael wasn't perfect, and he made a few bad decisions during his career. Dismissing Frank Dileo was one of them.
Despite it all, Dileo stayed on good terms with Michael. During the two molestation cases, Dileo spoke highly of his former client and defended him. He could have easily rubbed it in, saying "I told him to stop sleeping with those little boys, but he fired me." But he didn't. I could be wrong, but I think that Dileo was the only one of Michael's former managers to publicly defend him in 2005. Jackson was moved by this, and, remembering the glory days, re-hired Dileo a few months before his death. In fact, it was Dileo who told Michael's children that their dad was gone.
Dileo was a good guy. He was tough, husky and honest. I'm sure he's happy to be reunited with Michael again.