The president was asked why he'd sent well wishes to Maxwell - charged with child sex trafficking - at a recent White House press conference.
'Well, her boyfriend died in jail, and people are still trying to figure out how did it happen. Was it suicide? Was he killed? And I do wish her well,' Trump told Axios.
'I'm not looking for anything bad for her. I'm not looking bad for anybody.'
Probed on his compassion, Trump replied: 'Yeah, I'd wish her well. I'd wish you well, I'd wish a lot of people well. Good luck. Let them prove somebody was guilty.'
The president's relationship with Epstein and Maxwell has been scrutinized as they mixed in the same affluent circles for decades, with Trump once describing the convicted pedophile as a 'terrific guy'.
Trump knew Epstein and Maxwell for decades, running in the same elite social circles in Florida and New York in the 1980s and 1990s before the pedophile's fall from grace.
Epstein's sprawling waterfront property in Palm Beach, where many of his victims said they were lured to and sexually abused, is just 1.8 miles down the road from Trump's Mar-a-Lago club.
In 1992, the future president organized a 'calendar girls' party with 28 women, with Epstein and himself the only men, according to Vanity Fair.
The two men were also seen on recently surfaced video footage partying together that year at Mar-a-Lago with cheerleaders from the Buffalo Bills.
In the footage, Trump is heard saying: 'Look at her… she's hot.'
In 1997, Trump also flew from Palm Beach to Newark, New Jersey, on Epstein's plane with Maxwell also aboard.
TRANSLATION: "I am not saying shit about her. She has too much on me."
I fucking told all of you. Everybody ever seen on that island was receiving orders. If they did not comply? Total destruction through the release of compromising evidence through the mossad international media.