Maricopa County Sheriff Joe Arpaio was officially charged Tuesday with criminal contempt of court when a federal judge affixed her signature, a formality that throws the lawman’s political and personal future into a level of crisis never before seen in his 23 years in office.

Criminal-contempt charges have loomed over Arpaio since 2015. A criminal trial was the worst-case scenario for the sheriff after he admitted to violating a federal judge’s order to stop enforcing civil immigration laws.

U.S. District Court Judge Susan Bolton's order was signed two weeks before the general election, in which Arpaio is running for his seventh term.

A trial is set for Dec. 6 in U.S. District Court in Phoenix. If he’s convicted, the 84-year-old sheriff could face up to six months in jail, the Arizona Republic reports.

The sheriff aired his grievances in a recent campaign commercial.

“You know, this latest action by Obama and his Department of Justice is all about illegal immigration, period,” he tells the camera, against a photo backdrop of the president, former Attorney General Eric Holder and current Attorney General Loretta Lynch. “They’ve been after me since day one, for doing my job.”

Arpaio and his supporters said it was no coincidence that the Justice Department announced the charge on the eve of early voting.