Last spring, divorce proceedings began for the Giulianis after 16 years of marriage, setting off a rancorous battle that, like most everything Mr. Giuliani touches, demanded attention.

Despite the judge’s advice, a trial date has been set for January 2020, and the underlying reason, as it often does, stems from money.

A primary issue is Mr. Giuliani’s current income. His wife believes that Mr. Giuliani left his law firm, Greenberg Traurig, in 2018, a month after the divorce was filed, and chose to work for President Trump pro bono in order to reduce any future alimony.