There are internet feuds… and then there is the relentless, unstoppable avalanche known as Jimmy Kimmel vs. Donald Trump Jr. What started as a few monologue jokes has evolved into one of the most one-sided, hilariously brutal takedowns in late-night history — a masterclass in exposing hypocrisy, dismantling delusion, and turning a political dynasty’s heir into the world’s most reliable punchline.

And somehow, Donald Trump Jr. keeps walking right back into the fire.

The story begins with the moment Don Jr. first became a national meme: 2017, the year he tweeted evidence of his own wrongdoing.
Yes — the infamous “I love it” email chain with a Russian lawyer, promising political dirt. Instead of denying it, hiding it, or calling his lawyer, Don Jr. posted the emails online himself.

Jimmy Kimmel exploded with disbelief on his show:

“It’s the first time in American history someone voluntarily leaked their own crimes.”

The studio roared. It wasn’t just a joke — it was the birth of a running gag that would follow Don Jr. for years.

THE PATTERN: DON JR. HANDS KIMMEL MATERIAL, NIGHT AFTER NIGHT

From that moment on, Kimmel didn’t have to write jokes about Don Jr.
Don Jr. wrote them for him.

Every scandal, every rage-tweet, every awkward interview — Kimmel was there with a monologue ready to go. And Don Jr., desperate to be his father’s successor, kept offering himself up as the family’s most consistent source of public embarrassment.

Whether it was:

• rants about “chestfeeding” and supply chains
• attacks on journalists
• chaotic online videos
• disinformation tweets
• energy-drink-fueled CPAC speeches

…Don Jr. delivered fresh content with the reliability of a sitcom rerun.

WHEN DON JR. WROTE A BOOK CALLED TRIGGERED… AND BECAME THE MOST TRIGGERED MAN IN AMERICA

In 2019, Don Jr. published Triggered, a book claiming the “left can’t handle free speech.”

But the universe loves irony.

When he went on The View to promote the book, the interview collapsed into chaos. He was booed by the audience, snapped at the hosts, and looked like a malfunctioning bobblehead doll trying to defend himself.

Kimmel’s reaction?

“The only thing more awkward than this interview is Don Jr. realizing he’s not actually the favorite child.”

And it got worse.

At a Turning Point USA event at UCLA, DON JR.’S OWN CONSERVATIVE AUDIENCE booed him — loudly — because they weren’t allowed to ask questions.

A man selling a book about free speech… silencing the audience asking for free speech.

Kimmel nearly fainted from happiness.

THE WIKILEAKS DISASTER

Then came the Twitter leak of messages between Don Jr. and WikiLeaks.
Kimmel showed the screenshot:

“OFF THE RECORD.”

And said:

“This is WikiLeaks. The word ‘leaks’ is literally in the name.”

Don Jr. tried to downplay it.
Kimmel turned it into a sketch with “WikiLeaks” calling into the show to confirm the chaos — complete with eggplant emojis.

THE CPAC HYPERACTIVE-ENERGY MOMENT

Early 2020 brought another classic:
Don Jr. onstage at CPAC, sweating, yelling, pacing, vibrating like a malfunctioning wind-up toy.

Kimmel joked he looked like he’d consumed “twelve energy drinks and a raccoon.”

The audience howled.

THE COURT CASE — AND THE MELTDOWN

But then came the $250 million civil fraud case in New York — and suddenly Don Jr. had bigger problems than bad interviews.

Kimmel played the courtroom footage, calling him “Tiny Soprano”, mocking his inability to answer basic financial questions, and shredding the absurdity of Don Jr. trying to portray himself as a “business genius” while simultaneously claiming:

“I’m not an accountant. How am I supposed to know more than them?”

Kimmel replied:

“By that logic, insurance companies should sue patients for listening to their doctors.”

Don Jr. wasn’t helping his own case — legally or comedically.

THE RAGE AT KIMMEL

Any time Kimmel roasted him, Don Jr. responded with Twitter tantrums, calling him irrelevant, washed up, and controlled by the “Hollywood elite.”

Kimmel once replied:

“Washed up? Buddy… I have a show, a family, and a conscience. Pick one.”

Mic.
Dropped.

THE PROPAGANDA, THE FAKE VIDEOS, AND THE DESCENT INTO DISINFORMATION

As the years went on, Don Jr. pivoted to conspiracy content.
One moment he was tweeting doctored videos.
The next, he was spreading misinformation about global conflicts.

Kimmel called it out:

“Imagine being so desperate for attention you share fake propaganda while your dad is getting indicted.”

This wasn’t comedy anymore.
It was satire being forced to keep up with real-time chaos.

THE NEPOTISM JOKES

Kimmel frequently ridiculed Don Jr. as the Trump who:

• wasn’t the favorite
• wasn’t the smartest
• wasn’t the heir
• wasn’t even invited to the important events

He joked that Don Jr. wakes up every morning saying:

“Today’s the day I’ll make Dad proud.”

Then spends the next 24 hours proving why that will never happen.”

THE ULTIMATE HUMILIATION: THE FAMILY THAT FAILS TOGETHER

Kimmel skewered the entire Trump clan:

• the fake university
• the charity scandal
• the golf-course burial
• the nepotism
• the courtroom disasters

And every time Don Jr. tried to spin it, Kimmel shredded the spin on national television.

Don Jr. wasn’t the villain.
He wasn’t the mastermind.
He wasn’t the strategist.

He was the punchline.

A walking set-up joke in a suit two sizes too tight.

THE REASON THIS FEUD NEVER ENDS

Kimmel doesn’t attack Don Jr. because of politics.
He attacks him because the hypocrisy writes itself.

Don Jr. is claiming “fake news” while sharing fake videos.
Don Jr. is bragging about free speech while silencing audiences.
Don Jr. is calling Democrats elitists while tweeting from a gold tower.
Don Jr. is playing tough guy online while crumbling in interviews.

Kimmel doesn’t need to exaggerate.

He just needs to hit “play.”

And every time Kimmel hits that button, Don Jr. erupts — louder, angrier, and more embarrassing than the last time.

That’s why this feud is endless.

Don Jr. feeds it.
Kimmel amplifies it.
And America watches the loop like a sitcom that never stops being funny.