Sheik Abdulla bin Hamad Al Khalifa is suing Jackson for $7 million, money the Sheikh says was an advance for a music project Jackson abandoned.
Jackson says the money was a gift.
"When a family like that are so rich and they can buy stars to come and party with them, why would Michael Jackson think that this would be anything more?" celebrity journliast Neil Sean told CBS News.
On Friday, Jackson's former personal assistant told a British court that the sheik was a generous friend, eager to give Jackson money and other gifts.
Grace Rwaramba said Al Khalifa referred to Jackson as his brother and frequently offered the singer gifts and money.
"He would say, 'What can I do for my brother?' 'What can I give the children?'" Rwaramba said. "Mr. Jackson had a back pain and he told me to get Tiger Balm for him."
Rwaramba, who also was nanny to Jackson's three children, said she considered the sheik's behavior "sweet."
The sheik says Jackson reneged on a contract to produce an album, a candid autobiography and a stage play after accepting millions in advances. The money at issue includes sums of $35,000 and $1 million paid into Rwaramba's bank account by the sheik. Rwaramba said the money was intended for Jackson, who did not have a bank account of his own.
Rwaramba said she was "flabbergasted" when she received the first payment of $35,000, which she considered a large sum.
She said the sheik "apologized that it was a little. He said next time it would be more."
(AP Photo/Matt Dunham)The court heard that Al Khalifa (left) paid for hotel rooms for Jackson and his entourage and trips to Toys R Us to buy Christmas presents for the singer's guests.
Rwaramba said the sheik never suggested any of money would have to be paid back.
Jackson, 50, and the 33-year-old sheik first made contact when the King of Pop was fending off accusations of child molestation in California and Al Khalifa offered to help him. Once Jackson was cleared of the charges in June 2005, Al Khalifa invited him to the small, oil-rich Gulf state to escape the media spotlight.
Al Khalifa says he gave Jackson millions of dollars in all to help shore up his finances and subsidize Jackson's lifestyle in Bahrain - including more than $300,000 for a "motivational guru."
Al Khalifa, an amateur songwriter, says the pair even moved into the same palace to work on music together.
But Jackson dropped the project in 2006, leaving Bahrain and pulling out of the contract. Jackson's lawyers are arguing that the musician wasn't bound by the deal because the contract was signed on behalf of 2 Seas Records, a venture which never got off the ground.
But lawyer Robert Englehart told the judge on Thursday that Jackson's doctors had cleared him to travel.
Jackson may have made a fortune during several decades as a pop star, but he's also come close to being broke.
"When you are number one all around the world you are making a lot of money and he used to spend a lot of money at the same time," financial broadcaster Max Flint told CBS News. "The trouble is, he is not number one around the world anymore but he is still spending like it."
Jackson's money woes became more acute during his 2005 trial for child molestation. His ranch at Neverland, with its theme park, became a financial burden
By the time Jackson was acquitted, the Bahraini sheikh had befriended him, sent him money to pay legal expenses, and then invited him and his children to visit, hoping to kick-start his career
In an unrelated development, unconfirmed reports say Jackson may have converted to Islam last week - one more twist in a quirky career.
He says he wants every penny back. Jackson will tell the court he was a guest.