In an email request last month with the subject line "favor," Montgomery asked Supreme Court Justice Clint Bolick for a copy of his successful judicial application, according to records obtained by Phoenix New Times.
Governor Doug Ducey appointed Bolick to the Supreme Court in January 2016.
In the email exchange obtained by New Times under state public records law, Bolick agreed to track down the document at Montgomery's request. "Please let me know if you would like to talk at some point," the justice wrote back to Montgomery on the morning of January 9.
Bolick sent his application to Montgomery that afternoon, one day after the county attorney had emailed him asking for the document, the emails show.
Montgomery is one of 11 applicants for retiring Justice John Pelander's seat on the Supreme Court. In December, Pelander told the governor he intends to step down on March 1. Ducey will review applications from a judicial nominating commission before selecting the new Supreme Court justice, who will be the governor's fourth appointment to the bench.
The January email from Montgomery to Bolick marks the second time the justice and the powerful Maricopa County prosecutor have supported each another after a weighty political vacancy opened up.
Two days after the death of Senator John McCain last August, Bolick texted Ducey to recommend that he appoint Montgomery to the late senator's seat. Bolick praised Montgomery as "respected by everyone, supported by all parts of the GOP, yet unfailingly conservative."
“I hope you will consider Bill Montgomery, one of the few who could fill Sen. McCain’s shoes,” Bolick wrote on August 27.
Ducey replied, “Always value your advice and recommendations. I share your admiration of Bill. He is one of our finest."
The governor did not select Montgomery, and instead tapped former Senator Jon Kyl in September to temporarily fill the vacancy. Ducey later appointed Martha McSally to the seat, one month after she lost her Senate campaign to Democrat Kyrsten Sinema.
Bolick has said that he sent the Senate recommendation to Ducey unsolicited and did not discuss the matter with Montgomery beforehand.
In a phone interview on Friday, Montgomery said the purpose of his request for Bolick's document was simply to view the judicial application of a previous Supreme Court aspirant who, like him, had also not previously served as a judge. Bolick's application used to be listed on the Supreme Court's website but is no longer available, Montgomery said, explaining why he asked the justice for it.
Montgomery denied that anything about the exchange with Bolick was inappropriate, even when viewed in conjunction with Bolick's endorsement of Montgomery for the Senate.
"Despite what it might look like, I don't rely on Justice Bolick for career advice," Montgomery said. "And I did not ask him to weigh in with respect to Governor Ducey's appointment, ultimately of Senator Kyl."
"Justice Bolick is not my agent in seeking professional positions," Montgomery added. "And if he was, I would've fired him, because it didn't work."
Montgomery said he reached out to past Supreme Court applicants, including nearly every member of the Supreme Court, and as many commissioners on the nominating commission as possible before the application deadline.
It would "be foolish not to reach out to folks who had been successful, who had applied in the past, to see how they had answered some of the questions," Montgomery said.
However, no correspondence between Montgomery and Supreme Court justices besides Bolick was returned as a result of the records request.
Through a spokesperson, Bolick said the email exchange with Montgomery was the extent of their discussion of the county attorney's Supreme Court application.
Supreme Court spokesperson Aaron Nash wrote in an email, "Justice Bolick did not meet with Mr. Montgomery or discuss Mr. Montgomery’s application with him, although it is not unusual for candidates or people considering applying to the Court to speak with sitting justices about the job, and past judicial applications are available to anyone who requests them."
Colin Campbell, an attorney who served as presiding court judge on the Maricopa County Superior Court from 2000 to 2005, said he does not find the communication between Montgomery and Bolick to be untoward.
"I don't think the judicial rules of ethics preclude you from talking to people or saying, 'I've read your application and here's where I think it's weak or strong,'" Campbell said. "What it prevents you from doing is actively endorsing someone publicly."
The text message from Bolick to Ducey endorsing Montgomery for the Senate, however, is "of a different ilk," Campbell said.
Vacancies on Arizona's high court are reviewed first by the Commission on Appellate Court Appointments. From a field of 13 candidates, Montgomery and 10 others advanced to the interview phase last week, as the Arizona Capitol Times reported. After the interviews, the commission will send at least three candidates to Ducey for him to choose Pelander's replacement.
In 2016, Ducey appointed Bolick, a former libertarian litigator who has worked for the Goldwater Institute and the Institute for Justice, in what was the governor's first appointment to the Supreme Court. By selecting Bolick, Ducey passed over six other candidates, all of them sitting appellate judges.
When asked about his relationship with Bolick, Montgomery said, "I've known him for a very long time. He's a friend."
But, to explain his email request to the justice, Montgomery emphasized that the community of attorneys and judges in Maricopa County is smaller than people might realize.
He often comes into contact with members of the Supreme Court through professional functions, or their shared work on task forces or commissions, Montgomery said. Over the past several years, he has spoken with or had lunch with "just about every member of the Supreme Court."
"I just don't usually hold press conferences to announce who my friends are, so the fact that something like this looks like out of the ordinary is only because nobody knows how often I otherwise socialize with, or see, or interact with Justice Bolick, let alone any other justice," Montgomery said.