I agree with Judge Merchan. Fines do not change Trump’s behavior. Trump should not be allowed to keep violating the gag order.
However, if Trump is put in jail (where he definitely belongs), then the focus will shift to whether he belongs there instead of the crimes he is charged with. Trump will act like he is the victim.
The judge is in a no-win situation. He can tolerate intolerable behavior from Trump or help him by taking the attention away from the charges. There is no good solution.