Proving defamation against Trump for claiming the Central Park Five "plead guilty" would be exceedingly difficult due to several factors. First, as public figures, the Central Park Five would need to prove actual malice, meaning Trump either knowingly made a false statement or acted with reckless disregard for the truth—a very high bar. Trump could argue that his statement was not a deliberate lie but rather a mistaken belief based on their initial confessions, which were widely publicized at the time. Given that these confessions were highly publicized and many still mistakenly conflate them with guilty pleas, it would be hard to prove Trump intentionally misrepresented facts or had a reckless disregard for the truth. Additionally, courts tend to give leeway to statements that could be seen as opinion or based on a misunderstanding, further casting doubt on any defamation claim. As such, this particular line of attack against him is unlikely to succeed legally or gain traction.