A Republican operative with a history of illegal politicking has resurfaced in Arizona, where he was just paid six figures to place ads that won’t run for months.

KelliPAC, a group supporting GOP Arizona senate candidate Kelli Ward, paid a firm run by the operative, Jesse Benton, $268,000 this month to place television ads slated to run on August 2, just weeks before Ward faces off against former Maricopa County sheriff Joe Arpaio and Rep. Martha McSally in the state’s Republican primary.

“KelliPac is locking down airtime to before the August primary to make sure that Dr. Ward has the cover to prove she is the strongest conservative in the race,” Doug McKee, the group’s chairman, told The Daily Beast in an email.

McKee did not respond to follow-up questions about his decision to route the ad buy through Benton’s firm, Titan Strategies. Benton did not respond to a request for comment either.

Benton has been at the center of a number of high-profile political scandals, including one that ended with his conviction on four federal criminal charges. He is a former aide to Sens. Mitch McConnell and Rand Paul. He also worked Paul’s father, former Republican congressman and presidential candidate Ron Paul, whose granddaughter Benton married.

It was during his work for the elder Paul, that Benton ran afoul of federal law after engaging in a scheme to secretly pay an Iowa state senator to endorse the ex-congressman’s 2012 presidential campaign.

Benton avoided bribery charges in the case, but was found guilty of four charges related to the scheme. He was sentenced to two years probation and ordered to pay a $10,000 fine.

Prior to his conviction, Benton had been helping to run Great America PAC, a super PAC supporting Donald Trump’s presidential candidacy. Though he officially left the group after that conviction, Benton later offered to help disguise payments to the super PAC from individuals who he believed were wealthy Chinese nationals by funneling the money through Titan Strategies and a pair of “dark money” nonprofit groups.

A legal complaint filed with the Federal Election Commission regarding that proposal remains under consideration. Brendan Fischer, the director of federal reform programs for the Campaign Legal Center, the watchdog group behind the complaint, told The Daily Beast he was surprised to see Benton’s name resurface.

“Benton has certainly demonstrated a pattern of disregarding the law,” Fischer said in an email. “And somehow this guy keeps getting hired.”

As for the structure of KelliPAC’s payment to Benton’s firm, Fischer said it’s not unusual for political groups to reserve ad time in order to get better rates. “That being said,” he added, “it is not clear why an Arizona super PAC would pay a Kentucky political operative to buy Arizona airtime months in advance.”

The ad buy through Benton’s firm did come shortly after KelliPAC received a major cash infusion from a billionaire political donor who has supported both Rand and Ron Paul in the past. That billionaire, banker and professional poker player Andy Beal, wrote KelliPAC a $500,000 check three weeks before the group paid Benton’s firm.

A request for comment made through a Beal spokesman was not returned.

KelliPAC is Benton’s biggest client this cycle, by far. But he is also doing some work for another Republican senate candidate: Maine state senator Eric Brakey, who also ran Ron Paul’s campaign in the state.

Brakey, who is vying to challenge Independent Sen. Angus King, has made national headlines for dancing in a Brazilian bathing suit.