In 2000, Avram took Jackson to court again, this time suing the pop star for $21.2 million for pulling out of two New Year's Eve concerts. Those cancelled concerts, Avram alleged, left him $11 million in the red and resulted in another $10 million in lost profits.
But such a litigious history and Jackson's reported health problems weren't enough to scare off AEG. Concert organizers told ABC News they believed Jackson was ready for the 50-show run, especially given the careful way this particular concert series was organized.
"We are talking about 50 shows in one city, no travel and living in a beautiful estate in London," AEG Live CEO Randy Phillips said. "He was going to average two and a quarter shows a week."
Limiting the stress on Jackson's schedule was one of many, some would say, extraordinary precautions AEG took to make sure its star was stage-ready. At the pop star's request, AEG paid for Jackson's personal cardiologist to accompany him in London.
Jackson "looked me in the eye [and said], 'Look, this is the machine,' pointing to his body. 'This is the machine, that fuels this entire business, OK? ... I need a doctor 24/7,'" Phillips told ABC News.
Organizers also monitored Jackson's eating habits.
Choreographer Kenny Ortega "would cut his chicken breast and feed him," Phillips said. " ...In the last week, I brought in someone whose sole purpose was to remind him to eat. That was my biggest concern, was his weight."
AEG's purchase of a multi-million dollar policy for the concerts was another precaution, albeit not an uncommon one by some standards.
Experts say that while promoters may be loathe to shell out money to buy insurance for smaller acts, it's not unusual for promoters to buy cancellation and "non-appearance" insurance -- which specifically protects against a performer's absence -- for major stars. That, after all, is when millions of dollars are at stake.
Cancellation and non-appearance insurance can run tens of thousands of dollars per show, Moody said.
But, he added, "even if they paid $100,000 per concert for the cancellation and non-appearance, it's still worth it for a mega-headliner."
While AEG hasn't said how much it paid for Jackson's insurance, experts say that Jackson's history likely meant the company had to pay fairly high premiums.
Jackson "was basically blacklisted from doing concerts" without the benefit of a high-cost insurance, a Jackson associate told ABCNews.com.
For non-appearance insurance, in particular, underwriters require performers to undergo physicals. Jackson's physical lasted five hours and included "a battery of tests," Phillips told ABC News.
Both the physical and a star's history will determine how much an insurance company charges, said Candysse Miller, the executive director of the Insurance Information Network of California.
"Whether it's an entertainer, a car or home, [insurance is about] trying to somehow put a dollar value on the risk," Miller said. "If I live on top of the San Andreas fault, I'm going to pay a lot more for earthquake insurance."