There’s extremely stiff competition for the title of Worst Trump Surrogate. You’ve got Trump official campaign spokeswoman Katrina Pierson, who blamed Obama for the Afghanistan war.

And there’s Pastor Mark Burns, who tweeted a picture of Hillary Clinton in blackface and said Bernie Sanders doesn’t believe in God and needs Jesus.

There’s also Trump’s attorney, Michael Cohen, who once said spousal rape isn’t a thing.

And who can forget Trump veterans coalition co-chair Al Baldasaro, who said Hillary Clinton should be executed for treason?

But as luck would have it, Trump’s worst surrogate is in his very own family.

Trump’s eldest son, Donald Trump Jr., has distinguished himself with his rare gift for consistently embarrassing the campaign.

On Sept. 14, he told the Pittsburgh Tribune-Review that his dad wouldn’t release his tax returns because they would raise too many questions—instead of sticking to the (latest) explanation that the mogul is under audit and will release them once that process concludes.

When he spoke at the RNC, his speech generated allegations of plagiarism since some phrases sounded like they were lifted from an article that ran in the American Conservative magazine.

This week, a Trump aide yanked him out of an interview with a Pennsylvania TV station when the interviewer started asking him about the Trump Foundation.

And last month, he inadvertently criticized some of his dad’s top advocates, saying the Trump defenders who appear on CNN—people like former Reagan White House official Jeffrey Lord and conservative author Scottie Nell Hughes—have “no real political knowledge.”

And then there’s the penchant for interacting with the alt-right.

Whether it’s retweeting white supremacists, doing radio hits with white supremacists, or joking about gas chambers, DJT Jr. has proven remarkably adept at generating campaign crises.

The latest: comparing reporters to Nazis. Really.

“The media has been her number one surrogate in this. Without the media, this wouldn’t even be a contest, but the media has built her up,” he told the Philadelphia radio station WPHT on Wednesday. “They’ve let her slide on every indiscrepancy, on every lie, on every DNC game trying to get Bernie Sanders out of this thing. If Republicans were doing that, they’d be warming up the gas chamber right now.”

Trump later told NBC that he was referring to gas chambers used in the U.S., not the ones used by Nazis.

To his credit, at least Trump Jr. seems to think gas chambers are bad. He’s made a habit of retweeting and associating with members of the racist alt-right, an internet movement that is fond of using Nazi imagery and making Holocaust jokes. One alt-right site, for instance, has a feature called “The Daily Shoah.” And at a recent press conference in D.C., alt-right figure Richard Spencer defended “gas the kikes” jokes.

More than any other figure in Trump’s orbit, Don Jr. has repeatedly associated himself with the alt-right. Last week, he tweeted out a meme that first appeared on a white supremacist site and depicted the alt-right’s green frog mascot. The meme also showed him standing next to famed 9/11 truther Alex Jones. Hillary Clinton used the tweet to hit Trump, and her website put up a page saying the frog “is more sinister than you might realize.”

He also has a habit of retweeting white supremacists, maybe because he follows a bunch of them on Twitter.

For instance, two weeks ago he retweeted Kevin MacDonald, a professor beloved by Holocaust deniers who has written papers theorizing about Jewish media manipulation. MacDonald’s white nationalist political party, the American Freedom Party, posted a story about the retweet on its website along with a fundraising ask. In other words, white supremacists are literally fundraising off of Donald Trump Jr.’s twitter feed.

MacDonald isn’t the only white supremacist who Trump’s son has boosted. He also sent out a tweet from science fiction author Theodore Beale, who, as the New Republic noted, once said being gay is a “birth defect” and who has said that “being a Jew makes you not an American, by definition.”

Don Jr.’s alt-right flirtations aren’t limited to Twitter. In March, he did a radio interview with white supremacist radio host James Edwards, as the Huffington Post reported. On the show, Edwards told Trump Jr. he hoped his father would become America’s Charlemagne. And, as The Washington Post noted, Don Jr. didn’t take issue with that. Edwards said he also had no trouble getting press credentials for a Trump rally. In the past, Edwards has said slavery was good and interracial sex is bad. Don Jr. says he wasn’t aware of this at the time.

It shouldn’t come as a huge surprise that Don Jr. isn’t the universe’s best communicator. He’s spent his life saying weird things. For instance, when he toasted his mom at her wedding in 2008 (she remarried after divorcing from Donald Trump), he said she had “great boobs.”

In a 2012 radio interview, he said he supported gay rights because having fewer straight men around would make it easier for him to get laid.

“I think there was a time in my life, probably in college, that I wished every guy was gay, because it just meant more women for me!” he said, according to the Huffington Post. “‘I don’t know why you guys have a problem with this thing! I think it’d be great! I wish everyone was gay!’”

When he decided to stop chasing the women the gay men left for him, he chose the mall as the venue to ask his then-girlfriend, Vanessa, to marry him for a specific reason.

According to Gawker, he proposed to her in the New Jersey mall in front of a jewelry store so he could get the ring for free.

His Twitter feed is a trove of bizarre missives.

He once speculated as to whether the protagonist of the film War Horse had sexual relations with the aforementioned horse.

He also had some good takes on Snooki’s pregnancy——namely, that it shouldn’t have happened:

Now, the inability to stay on message could be to the fact he’s a businessman with a lack of experience in politics (sound familiar?).

But, instead of letting his gaffes and associations deter him from the profession, he appears to believe that he’s doing a really good job.

In a July interview on CNN, Trump Jr. declined to rule out a run for mayor in 2017.

“As my father has always said, I want to— we always like to keep our options open,” he said on State of the Union.

“So if I can do that as a service to our country I’d love to do it,” he said.