It’s no secret that President Trump and Jeffrey Epstein used to run in the same circle — but how close were they?

New photos and footage of Donald Trump and Jeffrey Epstein have been unearthed offering fresh insight into the pair’s relationship despite the president’s repeated attempts to distance himself. Epstein and Trump appear in a number of pictures surfaced by CNN and aired Tuesday night.

Here’s how Donald Trump’s position on Jeffrey Epstein has changed over the year, and how the fallout over the Epstein files poses a particular challenge for him.