If he joins Trump’s Cabinet, a history of controversial remarks will follow him. In recent years, Giuliani has sparked criticism for several offensive comments, while other remarks have helped to shed light on what his foreign policy might look like as Secretary of State.

Here are a few of Giuliani’s notable opinions and statements:

On President Barack Obama:
“I do not believe, and I know this is a horrible thing to say, but I do not believe that the President loves America,” Giuliani said at a private dinner in February 2015, according to Politico. “He doesn’t love you. And he doesn’t love me. He wasn’t brought up the way you were brought up and I was brought up through love of this country.”

In March 2015, Giuliani criticized the way Obama has spoken about race as president, suggesting he should say “the kind of stuff that Bill Cosby used to say.” More than 50 women have accused Cosby of sexually assaulting them, and many women had already come forward when Giuliani made the remark. Cosby has denied all the claims.

On alleged Russian intervention in the U.S. elections:
“I don’t think foreign powers should be intervening in U.S. elections,” he told reporters in July at a Republican National Committee press conference, according to the Huffington Post. The remarks followed Trump’s call for Russia to hack Hillary Clinton’s emails, after an investigation showed Russian operatives might have been responsible for the hack of Democratic National Committee files.

“Now, the reality of politics is that foreign powers do, and sometimes we intervene in their elections,” Giuliani said. “So, in an idealistic world, the reality is that foreign powers should stay the heck out of our election. We should stay the heck out of their elections”

On Russia’s relationship with the United States:
Asked at a Wall Street Journal event on Monday whether Russia was a “friend or adversary,” Giuliani said the country was both.

“Right now, it’s adversary because we made it that way. It could be both, just like China,” he said. “What I’d like to see China is to be an economic competitor as opposed to a military competitor. Russia thinks it’s a military competitor. It really isn’t. If you compare the size of our military and theirs, it’s our unwillingness under Obama to even threaten the use of our military that makes Russia so powerful.”

On military strength:
Asked at the same Wall Street Journal event on Monday what Trump’s military strategy will be as president, Giuliani used the phrase “peace through strength.”

“If you face them with a military that is modern, gigantic, overwhelming and unbelievably good at conventional and asymmetrical warfare, they may challenge you, but I doubt it,” he said. “[Mikhail] Gorbachev gave Donald Trump the answer to how to win. Gorbachev wrote in one of his memoirs—I think the principle one that he wrote—that, ‘Ronald Reagan spent us into oblivion,’ and I am a big advocate of military spending.”

On ISIS:
“We must not be afraid to define our enemy,” he said during his speech at the Republican National Convention in July. “It is Islamic extremist terrorism. For the purposes of the media, I did not say all of Islam. I did not say most of Islam. I said Islamic extremist terrorism. You know who you are, and we are coming to get you.”

He later added: “If they are at war against us — which they have declared — we must commit ourselves to unconditional victory against them.”

On the Iran nuclear deal:
Giuliani called it “one of the worst deals America ever made.”

“Obama’s nuclear agreement with Iran that will eventually let them become a nuclear power and is putting billions of dollars back into a country that’s the world’s biggest state supporter of terrorism,” he said during his RNC speech in July, when describing how the U.S. should defeat ISIS.

“We are actually giving them the money to fund the terrorists that are killing us and our allies. We are giving them the money! Are we crazy?”

On Syrian refugees:
“[Hillary Clinton] is in favor of even taking in Syrian refugees even though the Islamic state has told us they are going to put their operatives in with the Syrian refugees—operatives who are terrorists who are going to come through Western Europe and come here and kill us,” he said during his convention speech about Clinton’s willingness to accept more refugees into the U.S. “They’ve told us that, and she still wants to take in these Syrians.”

“We should not take them in,” Giuliani said last year in an MSNBC interview. “First of all, we shouldn’t take them in because the vetting process is a joke.” Pressed on how he would handle the refugee crisis, he added: “You pour them back into Syria, and you put them in a no-fly zone in Syria … Send them back to Syria, that’s where they belong.”

On Mexican immigrants:
Giuliani’s speech at the Commercial Finance Association’s “40 Under 40” dinner at New York’s Waldorf Astoria Hotel last month prompted an apology from the association’s CEO.

Attendees told the New York Observer that Giuliani talked about “Mexicans in the kitchen at the Waldorf” and spoke about Mexicans coming to the U.S. illegally to work in kitchens.

On Donald Trump’s lewd comments about women:
“The fact is that men at times talk like that, not all men, but men do,” Giuliani said in an interview with CNN in October, following the publication of a 2005 recording in which Trump boasted about groping women without consent.

When pressed about whether he had ever spoken that way, Giuliani said he believed the comments were wrong and that Trump had changed.

“He was wrong for doing it,” he said. “I am not justifying it. I believe it’s wrong. I know he believes it’s wrong. I believe that this is not the man that we’re talking about today.”

On Donald Trump’s tax avoidance:
“The reality is, this is part of our tax code. The man is a genius. He knows how to operate the tax code for the benefit of the people he’s serving,” Giuliani said in an October interview on CNN, regarding revelations that Trump used a business loss to avoid paying federal income taxes.

Giuliani made similar comments in a separate interview with ABC News. “Absolute genius,” he said. “This is a perfectly legal application of the tax code. And he would’ve been fool not to take advantage of it.”

On Hillary Clinton:
“Don’t you think a man who has this kind of economic genius is a lot better for the United States than a woman, and the only thing she’s ever produced is a lot of work for the FBI checking out her emails,” he said in an ABC News interview in October, while discussing the fact that Trump avoided paying federal income taxes.

After the first presidential debate in September, Giuliani also criticized Clinton for defending her husband in the 1990s amid the scandal of his sexual relationship with White House intern Monica Lewinsky.

“After being married to Bill Clinton for 20 years, if you didn’t know the moment Monica Lewinsky said that Bill Clinton violated her, that she was telling the truth, then you’re too stupid to be president,” Giuliani said.

On Beyoncé’s Super Bowl performance:
“I think it was outrageous,” he said in February about Beyoncé’s halftime performance, in which she showed support for the Black Lives Matter movement while nodding to the legacy of the Black Panthers. “This is football, not Hollywood, and I thought it was really outrageous that she used it as a platform to attack police officers who are the people who protect her and protect us, and keep us alive.”

On Black Lives Matter:
In a July interview on Face the Nation, Giuliani called the Black Lives Matter movement “inherently racist.”

“When you say black lives matter, that’s inherently racist,” he said. “Black lives matter. White lives matter. Asian lives matter. Hispanic lives matter. That’s anti-American and it’s racist.”

He also argued that the movement shouldn’t focus on police violence.

“If I were a black father and I was concerned about the safety of my child, really concerned about it and not in a politically activist sense, I would say be very respectful to the police, most of them are good, some can be very bad and just be very careful,” he said. “I’d also say be very careful of those kids in the neighborhood, don’t get involved with them because son, there’s a 99 percent chance they’re going to kill you not the police.”