Among the many bizarre dilemmas a Donald Trump presidency poses for Senate Republicans, this may be one of the weirder ones: A conservative majority that’s invoked Second Amendment rights and National Rifle Association grades to obstruct Democratic judicial and executive nominations may soon have to consider Rudy Giuliani, once the right’s loudest gun control advocate, as Trump’s choice for a top administration post.

As mayor of New York, Giuliani pressed for national gun registration, advocated bans on assault weapons and high-powered handguns, and birthed the strategy of suing gun manufacturers for negligence.

If selected as Trump’s secretary of state — as the rumor du jour predicts — Giuliani would be responsible for American policy with respect to international compacts, like the UN’s Arms Trade Treaty, that are seen by gun lobbyists as a backdoor to domestic firearms registration (and, of course, the New World Order).

Would the NRA and Senate GOP apply to Giuliani the same unrelenting pro-gun litmus test they’ve applied to President Barack Obama’s nominees for the better part of a decade? Or would they retreat from their principled, uncompromising gun-rights stance in deference to a new Republican administration’s nominee?

Even before last week’s election, campaign insiders had floated Giuliani as a potential appointee in a Trump administration. After failing repeatedly to translate his 9/11 fame into higher office, Giuliani came out early in support of Trump’s candidacy and established himself as one of the campaign’s most lively television proxies. On a victory tour with the press late last week, he indulged the nascent reports that he could be named attorney general. “I certainly have the energy” for the job, he told CNN’s Chris Cuomo, adding, “There’s probably nobody that knows the Justice Department better than me.” Now apparently out of the running for that job, Giuliani has coyly fed speculation that he has emerged as the frontrunner to run the State Department. At an event in Washington D.C. on Monday night, Giuliani said that another possible secretary of state pick, John Bolton, “would be a very good choice,” but that there were other, better options: “Maybe me, I don’t know,” he said.

Giuliani’s nomination to any prominent administration position could pose a special problem for Senate Republicans, particularly Majority Leader Mitch McConnell. Since mid-2009 — when President Obama nominated Sonia Sotomayor to the Supreme Court — the NRA has graded senators not just on their legislative positions, but on their votes for presidential nominees, as well. More than the lobby’s considerable campaign donations, the NRA’s longstanding practice of grading lawmakers’ gun-friendliness, from “A+” to “F,” has put the onus on Republicans and conservative Democrats to prove their Second Amendment bonafides with affirmative legislation. The scores, and many pro-gun voters’ deference to them, grant the NRA an outsize influence on politicians. But until Obama’s first term, the lobby had never considered confirmation votes in grading a politician’s fealty to its agenda.

As The Trace has previously reported, that shift in NRA grading came at McConnell’s request, as he sought ways to unite Republican Senators against the Obama administration. And the NRA ran with it, painting Sotomayor as an enemy of gun rights, despite the fact that she had never decided a gun case in 17 years as a federal judge. “We believe that any individual who does not agree that the Second Amendment guarantees a fundamental right and who does not respect our God-given right of self-defense should not serve on any court, much less the highest court in the land,” NRA leaders Chris Cox and Wayne LaPierre said in a statement condemning Sotomayor’s nomination to the high court.

From the NRA’s standpoint, the tack helped whip pro-gun senators into shape. Sotomayor was confirmed with only nine Republican “yes” votes. The following year, Elena Kagan was confirmed with the approval of only five GOP senators.

The NRA flexed its power again in 2014 against an unlikely opponent: Vivek Murthy, Obama’s pick to become surgeon general. Citing a 2012 tweet in which Murthy called guns “a health care issue,” the NRA lambasted the doctor for “partisan activism on behalf of gun control” and whipped GOP and pro-gun Democratic senators to vote no. Senator Rand Paul, who gets an “A” rating from the NRA, took the lead in opposing Murthy as a Trojan horse appointee who could “launch an attack on Americans’ right to own a firearm under the guise of a public health and safety campaign.” Opposition was so strong that Senate Majority Leader Harry Reid tabled Murthy’s confirmation until he could get a simple majority of Democratic votes in the Senate’s lame duck session.

The NRA gambit also extended to lower court appointments. Three times between 2010 and 2013, President Obama nominated Caitlin Halligan, an accomplished former state solicitor general from New York, to fill a federal appeals court vacancy left when John Roberts became a Supreme Court justice. The NRA came out publicly against Halligan’s nomination, saying she had been too eager to support lawsuits against the gun industry.

“The NRA has embedded itself so deeply into the culture of Republican politics,” Linda Greenhouse, the New York Times’ longtime Supreme Court reporter, mused in 2012, “that it would take a cataclysm to break the bonds of money and fear that keep Republican office holders captive to the gun lobby’s agenda.”

For the NRA, there could certainly be something cataclysmic about a Giuliani appointment. Since his election as New York mayor in 1993, he’s acted as a “national spokesman for gun licensing,” as Face the Nation’s Bob Schieffer once put it. “There’s no question we have to get much better control over the number of handguns and automatic weapons,” Giuliani told Schieffer, adding, “We just can’t sit here and let this kind of carnage go on. Gun licensing would help.” In 1995, Giuliani said that “the approach to gun control, the approach to assault weapons, at least by too many in the Republican party is a terrible mistake for the cities, a terrible mistake for America.” He continued: “The NRA is involved in a strategy that I don’t understand. I don’t understand fighting assault weapons — a ban on assault weapons.”

Again and again through the 1990s, Giuliani bucked the NRA and his party, even siding with President Bill Clinton on gun issues. Asked in 2000 by Tim Russert what he thought about “registration of all handguns,” Giuliani replied, “You know I’m for that.”

Giuliani’s gun control chatter was not idle talk. Though the NRA has declared all-out war on former New York Mayor Michael Bloomberg for suing gun manufacturers to stop illegal weapons from flowing into the city, the key lawsuit in that effort, New York v. Beretta, was originally filed in 2000 by Giuliani.

The narrative among Giuliani’s conservative supporters is that he’s had a change of heart since his past statements and acts in favor of gun restrictions. During his unsuccessful 2008 campaign for the GOP presidential nomination, Giuliani courted the NRA, saying in a speech to the group that the September 11 attacks on New York had changed his perspective in favor of Second Amendment rights. NRA members received the speech coolly, particularly after Giuliani interrupted his remarks to answer a phone call from his wife on the podium.

But as with Trump, Giuliani’s squishy Second Amendment positions have persisted. On MSNBC in 2013, Giuliani reaffirmed his support for universal background checks and “a database to keep guns out of the hands of drug dealers, criminals.” On the campaign trail this year, even as Giuliani questioned Hillary Clinton’s health and led rally attendees in cries of “lock her up,” he and Trump advocated a ban on gun sales to Americans on terror watch lists — a measure that the NRA opposed, but softened on publicly to keep in step with the GOP nominee.

Joseph Savino Jr. Arrest Conference -- US Attorney Rudolph W. Guiliani (C) holds machine gun with silencer as Assistant US Atty Paul Summit (l) and Chief Agent in charge from Alcohol and Tobacco and Firearms holds up two of the three automatic pistols with silencers that former City Councilman Joseph Savino from the Bronx bought seconds before his arrest today. He was also charged with income tax evasion as well. April 04, 1989. (Photo by Michael Schwartz/New York Post Archives / (c) NYP Holdings, Inc. via Getty Images)
In this 1989 image, Guiliani, then a U.S. attorney, poses with a machine gun seized from former Bronx City Councilman Joseph Savino. (Photo: Michael Schwartz/New York Post Archives / (c) NYP Holdings, Inc. via Getty Images)

“Giuliani’s image as a straight shooter risks being damaged by all the bobbing and weaving that he is doing over gun control,” gun lobby maven John Lott Jr. said of the ex-mayor during his presidential run. Conservative commentator Michael Gaynor was even more strident in an anti-Rudy column that the NRA highlighted on its website. “Giuliani does not make himself a conservative by calling himself one,” Gaynor wrote, “and he does not make himself a legitimate champion of gun owners by ignoring his anti-gun history and hoping gun owners won’t learn about it.” National Shooting Sports Foundation vice president Lawrence Keane said of Giuliani in a press release — which was picked up by the NRA’s bloggers — “You can’t pretend to be a supporter of sportsmen and gun-owners in New Hampshire when you tried to sue the firearms industry out of existence in New York.”

Can a lobby that once opposed a surgeon general nominee because of a one-off tweet about guns really now throw its support behind Giuliani, the Republican party’s most consistent anti-gun crusader of the past quarter-century?

It’s among the myriad questions Republicans and gun lobbyists face in joining their fortunes to Donald Trump, an inexperienced president-elect who is not known for intellectual consistency or honesty. The Senate’s, and the NRA’s, approach to a Giuliani appointment could indicate whether their primary concern is to advance conservative principles or preserve partisan power.

Representatives for Giuliani, Paul, and the NRA did not respond to The Trace’s requests for comment by press time. In an email, a spokesman for Senator McConnell wrote that “if the Leader issues any statements regarding potential nominees in the Trump Administration, we will be sure to let you know.”