The emails were sent Jan. 28, 2009, roughly four months before the singer's death. In the exchange, AEG Live General Counsel Shawn Trell said that he was going to Jackson's home to sign contracts for the "This Is It" shows later that year in London.
Ted Fikre, the general counsel for Anschutz Entertainment Group, wrote back in two minutes.
"Does this mean you get to meet the freak?" Fikre replied, according to the emails.
"Apparently. Not sure how I feel about that. Interesting for sure, but kind of creepy," replied Trell.
The emails followed testimony from the concert promoter's top attorney, who offered a different take on AEG's relationship with Jackson.
Fans rejoiced when Jackson announced his comeback tour, but according to testimony, his tour promoter, AEG, soon ran into a snag, obtaining insurance in case the show could not go on. It's required for all productions, according to Trell.
The problem, Trell told the jury, was a list of troubling reports in the British tabloids. The insurance marketplace was skittish. There were reports Jackson was in a wheelchair, that he had a back injury, lupus, and had suffered from cancer.
To calm fears, the broker obtained an independent medical exam. Trell says the broker stated that "other than a slight case of hay fever, he passed in flying colors."
Wednesday's questioning by AEG rebuts the portrayal by Katherine Jackson's attorney that AEG failed to tend to the pop star's health in pursuit of profits.
Trell testified that AEG could never profit from the insurance coverage and that it would only cover losses.
Michael Jackson died from an overdose of Propofol, which his doctor, Conrad Murray, used to treat Jackson's insomnia.
About that list of suspected maladies, the AEG attorney asked if it mentioned drug abuse, alcohol abuse or a sleep disorder. The answer: no.
Katherine Jackson's lawsuit alleges AEG hired Murray. Trell testified that Jackson hired him because the doctor had been treating him and his children for the three years prior.
Trell said Murray was an independent contractor, one of thousands routinely employed for 5,000 to 6,000 AEG projects staged every year.
Trell highlighted language in the independent contractor agreement that it would not take effect without the express and written approval of the artist. Jackson, he noted, never signed it.
As Trell winds up testimony, another AEG executive prepares to take the stand. CEO Paul Gongaware, who is named in the lawsuit, will be the first of the defendants to testify in the case.
The Associated Press contributed to this report.