In text messages obtained by Phoenix New Times under state public records law, Bolick wrote to Ducey on August 27, asking him to tap the polarizing Republican prosecutor for McCain's Senate seat.
“I hope you will consider Bill Montgomery, one of the few who could fill Sen. McCain’s shoes,” Bolick wrote. “He is respected by everyone, supported by all parts of the GOP, yet unfailingly conservative. Wicked smart, principled, West Point, very modest beginnings, young enough to be there for a long time. Can work across the aisle.”
“Bill has not asked me to do this; to the contrary it would require an appeal to his sense of duty,” Bolick added.
Bolick described Montgomery as “conservative to my libertarian yet there are few I respect more, very much in the mold of [former U.S. Senator] Jon Kyl.”
He went on to wish Ducey good luck during the governor's re-election campaign and referred to his own then-upcoming judicial retention election.
“It will be an honor to appear on the ballot with you this fall – good luck, we need you,” Bolick wrote.
In return, Ducey thanked Bolick and indicated that he, too, appreciates Montgomery.
“Always value your advice and recommendations. I share your admiration of Bill. He is one of our finest,” Ducey wrote.
The governor ultimately appointed former Senator Jon Kyl to fill McCain's seat.
Kyl has indicated that he may not serve beyond the end of this Congressional session, leaving the door open for Ducey to potentially appoint another individual.
Montgomery was first elected as Maricopa County attorney in a 2010 special election, and voters have re-elected him twice since then. He is a staunch opponent of marijuana legalization, medical or otherwise, and has a track record of opposing criminal-justice reform bills that could help reduce Arizona's incarceration rate, which ranks fourth-highest nationwide.
A spokesperson for Montgomery did not respond to requests for comment.
When asked about his comments, Bolick explained in an email that he was expressing his beliefs for the Senate appointment – as well as his political support for Ducey – in his capacity as a private citizen.
Arizona's judicial ethics rules allow judges to privately express support and make political contributions, Bolick said.
"I conveyed privately to the governor that I thought Bill Montgomery would make an excellent appointee as senator," Bolick wrote to New Times. "I thought my knowledge of Bill, especially as someone with whom I have some differences of opinion, might be helpful to the governor. Bill had no knowledge that I was doing so and I acted in my capacity as a private citizen."
"Similarly, I privately expressed my support to the governor," Bolick wrote. "It would have been permissible to contribute to him, and many judges make contributions to candidates. I did not, however, as such public support could lead to a conflict in my view."
He declined to comment further.
A former crusading libertarian attorney, Bolick previously served as the vice president for litigation at the Goldwater Institute. In 2016, Ducey appointed him to the Arizona Supreme Court in the governor's first opportunity to fill a vacancy on the high court, but some saw Bolick as an unusual choice given that he was not a sitting judge.
This year, educators in the #RedForEd movement blamed Bolick and other Republican-appointed justices for scuttling the Invest in Education initiative that aimed to raise taxes to fund schools. They had threatened to vote out Bolick and Justice John Pelander, the other Supreme Court judge who was up for retention this month. Arizona Supreme Court justices must stand for a retention election two years after they are appointed, and every six years going forward.
Bolick and Pelander easily survived their retention elections anyway, with over 70 percent of voters backing them.
The relationship between Ducey's office and members of the Arizona Supreme Court has been under close scrutiny in recent months, also because of the ill-fated Invest in Ed initiative.
After the Supreme Court kicked the measure off of the ballot in a brief order on August 29, the vote count in the controversial decision apparently leaked to one of Ducey's campaign operatives, Daniel Scarpinato, ahead of the court releasing a full-length opinion.
Scarpinato denied that someone at the Supreme Court tipped him off to the 5-2 vote count. What appeared to be a strategic leak designed to deflect blame from Ducey and his three Supreme Court appointees was mere gossip, Scarpinato claimed.
In the aftermath, Chief Justice of the Arizona Supreme Court Scott Bales launched an inquiry, which produced little evidence of a clear-cut leak.
In emails obtained by New Times, Bolick told Bales at the time that the only people who learned the vote breakdown from him were his clerks and a judicial assistant.
Bolick's wife, Shawnna, happens to be a politician, too. Earlier this month, she won her third campaign to join the Arizona House of Representatives, and will represent Legislative District 20 alongside incumbent Republican Anthony Kern.
Even though Montgomery did not get the nod, Bolick appeared to be pleased with Kyl's selection. "Great choice, on many levels," he wrote to Ducey on September 4, the day of the announcement.
"Thank you Justice!" Ducey replied.
Responding to questions about the possibility of Ducey appointing Montgomery as well as the governor's chummy exchanges with a sitting justice of the Supreme Court, Ducey spokesperson Daniel Ruiz wrote in an email, "The governor filled the Senate vacancy on September 4th with the appointment of Jon Kyl. There is currently no vacancy to fill." He did not elaborate.
Other text messages between Ducey and Bolick obtained by New Times reveal text correspondence that is warm and friendly, if somewhat sporadic.
On January 22, Bolick texted Ducey to recommend Republican Chris DeRose for the position of Maricopa County Superior Court clerk. Sure enough, in March, Ducey appointed DeRose for the interim position of clerk after his predecessor retired. (DeRose lost in the Republican primary in August to Jeff Fine.)
A few days later, on January 26, Bolick asked Ducey if he had seen a New York Times interview with California Governor Jerry Brown in which Brown received a call from Ducey and at first didn't recognize the Arizona governor's name. "You could use that anecdote to update your references to him ('I was just calling to thank him for everything he does to improve the economy – Arizona's economy,'" Bolick suggested.
"Good idea!" Ducey wrote back.