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Seated in front of a computer at his Mar-a-Lago resort, Donald Trump will be asked to explain, politely, why he is a man who can be trusted.

The former president has been judged by a jury of his peers, being found guilty of 34 felonies. It is now time, in the eyes of the New York criminal justice system, to devise a fitting punishment. Accordingly, a probation officer on Monday will ask Trump, via video conference, whether he accepts responsibility for his crimes; they will assess his finances (and his mental health); they will consider his family life and ties to community; and they will want to know whether the presumptive Republican nominee continues to associate with criminals.

The list of past and present members of Trumps inner circle who have been found guilty of serious crimes is long and growing. Just this year, two of his former White House aides, Peter Navarro and Steve Bannon, were sentenced to prison for defying congressional subpoenas. Allen Weisselberg, former chief financial officer of the Trump Organization, is currently on Rikers Island. Paul Manafort, Trumps 2016 campaign manager, and MAGA dirty-tricks specialist Roger Stone each received multi-year prison sentences only to be freed by Trump pardons.

"[Former] President Trump has surrounded himself with a bunch of killers who work every day to help him win," as Trump campaign spokesperson Steven Cheung put it to Axios in March. If thats still the case come July 11, when Trump is due to be sentenced by Judge Juan Merchan in his hush-money case, that could be a serious problem

Theres nothing wrong with his telling the probation office, I didnt do anything wrong, and Im not admitting guilt, and Im planning on appealing, Andrew Weissmann, a former federal prosecutor, told MSNBC. Every defendant has a right to do that.

More difficult, Weissmann said, will be the question about whether Trumps still associating with criminals.

Hes going to have to discuss whether he still coordinates with Roger Stone, Paul Manafort, Steve Bannon. Remember, all those people have been found guilty by a jury and are felons themselves, Weissmann noted.

In March, CNN reported that Manafort was in discussions with Trumps campaign team about a possible role going forward. But last month, citing the media and its desire to use me as a distraction, Manafort said that he would not be doing any formal campaign work but helping from the sidelines every other way I can.

But as for Stone, hes been a frequent presence at Mar-a-Lago lately, Axios reported in March, noting that he attended Trumps victory party there on Super Tuesday.

Going forward, such a celebration could land Trump behind bars himself.

Barbara McQuade, a former U.S. attorney who teaches law at the University of Michigan, told MSNBC that the terms of probation that Trump will likely have to comply with may prove difficult. A prohibition on associating with other convicted felons, typical in cases of other offenders, would in particular be challenging for him.

But if hes not willing to comply with those kind of conditions, his alternative is prison, McQuade said. Given his other legal troubles, and his repeated contempt violations in the hush money case, its possible hes headed that way regardless. Manhattan District Attorney Alvin Bragg would at least be justified in requesting it, according to McQuade.

I think in light of the way that Donald Trump violated the gag order in this case and his continued lack of remorse in this case, she said, [it] would lean heavily in favor of requesting at least some prison time.

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about Trump's legal problems

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Legal expert: Probation terms may prove "challenging" for Trump but "his alternative is prison" - Salon