The emails detail concerns over the 50-year-old pop icon's health by those around him in the days and weeks before his death, reported New York Daily News.
Kenny Ortega, the director of his ill-fated "This Is It" comeback tour, sent an email in the predawn hours of June 20, 2009, telling promoter Randy Phillips, the head of AEG Live, that Jackson appeared too "weak and fatigued" to rehearse the previous night, "trembling, rambling and obsessing" so much that Ortega recommended a psychological exam.
Ortega fired off another email 11 hours later, saying, "I honestly felt if I had encouraged or allowed him on stage last night he could have hurt himself."
Phillips responded: "You cannot imagine the harm and ramifications of stopping the show now... Please stay steady. Enough alarms have sounded. It is time to put out the fire, not burn the building down."
The 250 pages of emails were sent in the run-up to Jackson's death in June 2009 and the months after. The emails are expected to play a central role in two lawsuits - one involving Jackson's heirs suing AEG for wrongful death.
The other is a battle over the USD 17.5 million insurance policy that Lloyds of London wants rejected due to Jackson's alleged ailments.
A lawyer for AEG said the leaked emails were "cherry-picked" from more than 40,000 documents in an effort to "misguide" the public.