Trump is forcing judge 'into horrible decision' with violations of gag order: analysis

Donald Trump keeps testing the boundaries of court-imposed gag orders – and even some of his current and former allies have conceded that he might wind up in jail.

Judge Arthur Engoron has already fined Trump twice, totaling $15,000, for disparaging his court clerk, and Fox News broadcaster Jesse Watters, former White House lawyer Ty Cobb and current Trump attorney Alina Habba have all wondered aloud whether he could be jailed — though judges have other options, wrote Washington Post columnist Aaron Blake.

“I would be extremely reluctant to take a person who is a former president, the leading candidate of one of our major parties, and put him in jail,” said Eric Holder, the former attorney general under Barack Obama.

Holder speculated recently that a judge could move to restrict Trump's access to social media, which could pose a number of problems under the First Amendment. A legal expert suggested he could be confined to an apartment or house without social media.

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“That would be gentler than prison, but with many of the same restrictions,” said Catherine Ross, an expert on gag orders at George Washington University.

But that would open the same First Amendment questions and raise other concerns about traveling for his 2024 presidential campaign, and that's another big reason why judges would be uncomfortable throwing him in jail, even for a weekend.

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"Trump has a talent for forcing people into unavoidably horrible decisions they’d rather not have to make," Blake wrote.