It's difficult to argue convincingly whether Trump is winning or losing his plethora of legal battles, as the former president continues to undermine the very essence of any legal process: following the rules. While it is unlikely that Chutkan will be removed, Trump has shown himself willing to go down any viable avenue – regardless of its merit – in order to delay these proceedings.
While Chutkan's prejudicial comments against Trump are extraordinary, they are hardly a surprise. A former employee of Boies Schiller, who had previously represented and defended Hunter Biden, Judge Chutkan clearly has conflicts of interest that disqualify her as an impartial judge.
There's a 50% chance that Donald Trump will be jailed or incarcerated before 2030, according to the Metaculus prediction community.