Looks like Trump capo Allen Weisselberg may face charges this summer. As we know, a New York grand jury has been hearing evidence and the prosecutors have been pushing the financial officer to take a deal in exchange for testifying against Trump. Via the New York Times:
The investigation into Mr. Weisselberg focuses partly on whether he failed to pay taxes on valuable benefits that Mr. Trump provided him and his family over the years, including apartments and leased cars as well as tens of thousands of dollars in private school tuition for at least one of his grandchildren. In general, those types of benefits are taxable, although there are some exceptions, and the rules can be murky.
[...] As part of the investigation into the fringe benefits Mr. Trump provided, Mr. Vance’s prosecutors have sought records for Mercedes-Benz cars leased for Mr. Weisselberg, his wife and other Trump Organization employees over the course of more than a decade, according to a person with knowledge of the matter.
The full scope of the investigation into Mr. Weisselberg, including whether prosecutors are considering other charges against him separate from the fringe benefits, could not be determined. It is rare for prosecutors to build a criminal case solely around a failure to pay taxes on fringe benefits.
I don't know exactly how much wiggle room Weisselberg has here, but I can tell you from experience: If his wife co-signed joint tax returns (and it's likely that she did), prosecutors will often pull the "your wife is going to jail unless you cooperate" card. I remember one case where they went after the federal pension of a postal worker because his wife was getting paid under the table for the target of their investigation -- and the husband signed their tax return.