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These repeated failures by the judge to enforce the rules within the court will not fortify the result of the decision on appeal.
The thing is, if they hit Trump with a contempt of court order, and then jail him, that can be used to claim that the judge was biased against him, unless that kind of punishment is typical for violating gag orders repeatedly. So you want to avoid that, since that makes it easier to claim that the judges instructions and handling of the case was also biased.