5 comments that got Donald Trump Jr. in hot water

— -- Donald Trump Jr.’s meeting with a Russian attorney in June 2016 adds a new twist to the ongoing investigation into whether Trump associates colluded with Russia to meddle in the 2016 election. The latest controversy, however, is not the first time that President Trump’s namesake stirred controversy.

Here’s a breakdown of five times Donald Trump Jr. appeared to draw negative attention to Donald Trump Sr., both as a presidential candidate and as president.

1. Donald Trump, Jr. Meets With Russian Attorney in June 2016

This week, Trump Jr. tweeted what he said are screen shots of an email chain arranging a June 2016 meeting with Russian attorney Natalia Veselnitskaya, who he was told had damaging information about Hillary Clinton. The meeting occurred when then-candidate Donald Trump Sr. was gearing up for a general election fight against Hillary Clinton. Also present at the June 2016 meeting were one-time Trump campaign chairman Paul Manafort and Jared Kushner, a current White House senior advisor and the president’s son-in-law.

Since news of the meeting broke, Trump Jr. has tweeted calling it a "nonsense" meeting. In a statement, he said he was releasing the email chain to be "totally transparent.”"

President Trump said in a statement from his deputy press secretary, "My son is a high-quality person and I applaud his transparency."

Trump Jr. has hired a lawyer and said that he will be happy to talk to the Senate committee as they continue their investigation into Russia’s interference in the 2016 election.

In an appearance on Fox News July 11, Trump Jr. said he would never have done anything to endanger the country.

“If there was something that came from it that was shady, if it was a danger to national security then I would obviously bring it right to someone,” Trump Jr. told Sean Hannity.

“It was such a nothing,” he said. “There was nothing to tell.”

Trump Jr. did not apologize for the meeting, but acknowledged that, in hindsight, he may have made different choices.

“Like I said, in retrospect, I probably would have done things a little differently,” he said. “Again, this was before the Russia mania, this was before they were building it up in the press. For me this was opposition research.”

“I just wanted to hear it out,” Trump Jr. continued. “But, really, it went nowhere and it was apparent this was not what the meeting was actually about.”

2. Donald Trump Jr. Appears to Corroborate Comey’s Testimony

While fired FBI Director James Comey was testifying before the Senate Intelligence Committee on June 8, Donald Trump Jr. took a page from his father’s playbook and tweeted throughout Comey’s testimony.

At one point, Trump Jr. appeared to corroborate a key part of Comey’s testimony and contradict his father. In his prepared statement, Comey described a meeting where President Trump had talked to him about disgraced former NSA director Michael Flynn. Comey said that Trump had told him, "I hope you can see your way clear to letting this go, to letting Flynn go." He also described the president asking for his loyalty.

When asked further about these conversations by the Senate committee, Comey said, "My common sense told me what’s going on here is he's looking to get something in exchange for granting my request to stay on the job."

Trump Jr. tweeted during the testimony, "Knowing my father for 39 years when he 'orders or tells' you to do something there is no ambiguity, you will know exactly what he means."

Following Comey’s testimony, President Trump denied that he ever asked the former FBI director to let the Flynn investigation go.

A few days after the testimony, Trump Jr. gave an interview to Fox News' Jeanine Pirro, during which he defended his father, but also seemed to contradict him.

"When [President Trump] tells you to do something, guess what, there's no ambiguity in it," Trump Jr. told Fox News on June 10.

"There's no, 'Hey, I'm hoping,'" Trump Jr. said. "You and I are friends, 'Hey I hope this happens, but you've got to do your job.' That's what he told Comey."

3. Donald Trump Jr. Compares Syrian Refugees to Skittles

During the heat of the general election campaign, Trump Jr. tweeted in defense of his father’s proposed plan for extreme vetting of immigrants and a ban on Syrian refugees.

In September 2016, Trump Jr. tweeted an image of a bowl of Skittles with a graphic that asked the question, "If I had a bowl of skittles and I told you just three would kill you. Would you take a handful?"

Trump Jr. later defended his tweet at a press conference in Boise, Idaho on Sept. 22, 2016.

"To me it was a simple metaphor," Trump Jr. said. "You know people will today make what they want of anything, and they see the worst in everything and they look for subtext that doesn’t exist."

4. Donald Trump Jr. Likens Media Bias to a Gas Chamber

In September 2016, Trump Jr. likened media bias to a "gas chamber." His remarks drew criticism from the Anti Defamation League for making what they called "Holocaust jokes."

Trump Jr. denied he was referencing the Holocaust in an interview with ABC News’ George Stephanopoulos.

"I didn’t say anything about the Holocaust. I was talking about media bias," Trump Jr. said on "Good Morning America" on Sept. 16, 2016. "It was a poor choice of words, perhaps, but in no way shape or form was I ever even remotely talking about the Holocaust. I wouldn’t do it. I think it’s disgusting. It’s not my style."

5. Donald Trump Jr. Posts Image With Pepe the Frog

The president’s eldest son also sparked controversy when he posted to Instagram a photo that showed Pepe the Frog, an image frequently used by the alt-right.

Trump Jr. posted the image in September 2016 as a reaction to Hillary Clinton’s campaign gaffe where she referred to Trump supporters as a "basket of deplorables." The image replaced characters from the movie "The Expendables" with alt-right figures like Alex Jones and Milo Yiannopolouos. It also had images of Donald Trump Sr., Donald Trump Jr., now Vice President Mike Pence and other Trump allies like New Jersey Governor Chris Christie and Roger Stone. Across the image was the phrase, "The Deplorables."

In a September 16, 2016 interview with ABC News’ George Stephanopoulos, Trump Jr. said, "I’d never even heard of Pepe the Frog. I mean, I bet 90 percent of your viewers haven’t heard of Pepe the Frog. I thought it was a frog in a wig. I thought it was funny. I had no idea that there’s any kind of connotation of there."

ABC News' John Santucci contributed to this report.