Flake donates to Democratic sheriff being challenged by Arpaio in Arizona
© Greg Nash

Former Arizona Sen. Jeff FlakeJeffrey (Jeff) Lane FlakeCheney set to be face of anti-Trump GOP The unflappable Liz Cheney: Why Trump Republicans have struggled to crush her  Cindy McCain: Arizona election audit is 'ludicrous' MORE (R) announced Wednesday that he donated to Paul Penzone, the Democratic sheriff of Maricopa County who is facing a challenge from Joe Arpaio, the county's former sheriff. 

Flake tweeted a picture of a check he sent to Penzone’s campaign for $100, writing in the memo line, “County over Party.”

Flake has emerged as a chief GOP critic of the party's direction, decrying President TrumpDonald TrumpKinzinger, Gaetz get in back-and-forth on Twitter over Cheney vote READ: Liz Cheney's speech on the House floor Cheney in defiant floor speech: Trump on 'crusade to undermine our democracy' MORE’s rhetoric and admonishing congressional Republicans for their overwhelming support for the White House.

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He donated to Democrat Doug Jones in the 2017 Alabama Senate race after Republican Roy MooreRoy Stewart MooreThe Hill's Morning Report - Biden assails 'epidemic' of gun violence amid SC, Texas shootings Trump faces test of power with early endorsements CPAC, all-in for Trump, is not what it used to be MORE was hit with multiple allegations of sexual misconduct and assault by several women who said at the time of the incidents they in their teens and he was in his 30s. Jones went on to win the race.

Arpaio, who was sheriff of Maricopa County from 1993 to 2016, announced in August he would run for his old seat in 2020.

"The last four years have proven to be a time of lost opportunities to continue the kind of tough policing this county needs," Arpaio said in a statement. "Once back in office, I will use my position to restore pride to our law enforcement ranks, not only here, in the fourth-largest county in America, but across the country."

Arpaio sparked nationwide criticism for housing some of the prisoners under his supervision in outdoor “tent cities” and using so-called chain gangs during his time as sheriff.

He was also convicted on criminal contempt of a federal court after he refused to follow an order that he cease detaining people based on their immigration status, though Trump pardoned him in 2017.