Michael Jackson’s public image could seem quiet and carefully controlled, but people close to him knew he had a mischievous side.
His manager Frank DiLeo experienced it firsthand.
Michael told the story himself in his autobiography Moonwalk. During the 1984 Victory Tour, Michael and Frank were standing on a hotel balcony in Washington, D.C., teasing each other when Michael suddenly began reaching into Frank’s pockets.
What he found was cash.
Not small bills either.
Michael started pulling out $100 bills and throwing them from the balcony to people walking below. He remembered that the sudden shower of money nearly created chaos as people scrambled for it.
Frank tried to stop him, but according to Michael, both men were laughing.
When the prank finally ended, DiLeo even sent security downstairs to search the bushes for any money people had missed.
The story happened while the Jacksons were in Washington for the Victory Tour. Records confirm the group performed at RFK Stadium on September 21 and 22, 1984, with DiLeo already serving as Michael’s personal manager.
Michael Jackson Punk’d Frank DiLeo
Frank was much more than another executive in Michael’s circle.
Before becoming Michael’s manager in 1984, he had been an executive at Epic Records and played an important role in promoting Thriller. Michael then hired him as his personal manager while his career was reaching extraordinary heights.
That close relationship apparently made Frank an easy target.
In Moonwalk, Michael recalled another prank during the same tour involving his boa constrictor, Muscles.
Michael knew Frank was terrified of snakes. He arranged for Frank to encounter Muscles in his hotel suite and then chased him with the snake. Frank became so frightened that he reportedly ran from the room and reached for a security guard’s gun before being calmed down.
The stories reveal a side of Michael that audiences rarely saw.
Touring meant stadiums, security and enormous pressure, but it also meant long stretches trapped inside hotels with little freedom to go outside.
Michael wrote that practical jokes helped recreate some of the fun he remembered having with his brothers when they were younger.
Frank DiLeo remained one of the most important people from Michael’s peak years, overseeing major parts of the period surrounding the Victory Tour, Bad and Michael’s growing global career.
But sometimes managing the King of Pop apparently meant something much simpler:
checking your pockets before Michael Jackson decided to throw your $100 bills off the balcony.