Was Michael Jackson a Shrewd Businessman or Underhanded Friend?

June 28, 2009 — -- When they first met in the 1970s, they were two of the most famous entertainers on earth -- Michael Jackson and Paul McCartney.

They became good friends. Their partnership in the early 1980s produced hits like "Say Say Say" and "The Girl Is Mine."

"They're pure pop lovers with some of the greatest sense of melody," former editor in chief for Vibe and Spin magazines Alan Light told ABC News. "And students of old Hollywood films and early rock 'n' roll records, and lovers of cartoons. There was a lot of common ground between them."

But the relationship between Jackson and McCartney soured in 1985. That year, Jackson entered into a bidding war with McCartney for the rights to the Beatles song-copyright catalog. Jackson won, paying $47.5 million for more than 200 songs, including classics such as "Yesterday" and "Let It Be."

The details of the 10-month negotiations never became entirely clear.

"The story goes that one day at Paul McCartney's house they were having dinner and Paul casually mentioned that the way to make real money in the music business is through publishing," New York Times music reporter Ben Sisario told ABC News. "Michael took that to heart."

Alan Light said, "One thing that was speculated was that Michael kind of knew how much Paul was going to bid for this and knew what it was going to take to top that bid."

Although Jackson's financial affairs are now reportedly in disarray, Sisario said the acquisition of the songs was the move of a very smart businessman.

"Michael Jackson's investment in the Beatles' catalog was one of the most brilliant coups in all of music history," Sisario told ABC News. "He got his hands on the most valuable songs that there are for a pretty small amount of money. That has ballooned from about $50 million into more than a billion dollars."

But McCartney was furious, and the two reportedly didn't speak for years.

"You know what doesn't feel very good," McCartney said as recently as 2006, "is going on tour and paying to sing all my songs. Every time I sing 'Hey Jude,' I've got to pay someone."