Jimmy Kimmel Roasts Trump on Episode 4000 After Summer Break

Jimmy Kimmel fired off a scathing verbal assault on President Donald Trump in his very first episode back from summer vacation, ignoring the fresh rumors that his late-night career is winding down by next year. The comedian stepped onto the stage Tuesday night for the 4,000th episode of Jimmy Kimmel Live after a three-month break. Sources told Page Six that this 24-year television run ends in 2027, though they insisted the attacks on Trump were not why it will stop.

Kimmel, 58 years old, said nothing about those reports and spent his entire 15-minute monologue dismantling the president's record. "Donald Trump and I have one thing in common," he told the crowd. "We both accomplished nothing all summer long." He walked through a list of disasters involving Trump and the White House, claiming that when he left for vacation in June, the country was already a mess.

The host rattled off the war with Iran, skyrocketing gas prices, high inflation, and Kentucky Senator Mitch McConnell, noting that nobody knew if the senator was alive or dead at certain points. Kimmel then mocked Trump's botched $20 million Reflecting Pool makeover, calling the landmark a "big green slop hole" while displaying images of its murky water.

Tuesday's episode aired just hours after sources revealed to Page Six that Kimmel's late-night run is set to end next year. During the segment, Kimmel quipped, "Now, only three months later, I'm so pleased to report that thanks to your favorite president, DJ Jazzy Donald, every one of those problems has been solved, we made America great again!" The comedian used sarcasm throughout.

Earlier this week, the Reflecting Pool found itself in yet another mess after powerful storms left the site surrounded by toppled fencing, fallen trees, dirty rainwater and debris. This happened just days after Trump claimed the project was "almost completely fixed." It is the latest setback for a repair effort that started in April to turn the pool "American Flag Blue," a job the White House said would take only a few weeks.

"The president had three months, spent 20 million dollars and couldn't even get a pool cleaned," Kimmel stated during Tuesday's show before showing recent photos of the Reflecting Pool covered in tarps and filled with dark liquid. "I thought he was supposed to drain the swamp, he turned it into gravy instead." He joked that Trump might be pumping the pool with Diet Coke, a comment that made the audience laugh.

"How are we supposed to win the war with Iran when we can't even win the war against algae for God sake," Kimmel added. The host then shifted focus to Trump's standing with voters, declaring that "Trump's poll numbers and pool numbers are at all-time lows.

Only thirty-three percent of registered voters approve of the president's job performance. That is exactly what Jimmy Kimmel claimed during his monologue last night. He argued that with one in three people disapproving, Donald Trump is doing everything possible to stop Americans from voting in the midterms. The host mocked the recent botched makeover of the Reflecting Pool. Trump spent twenty million dollars on a project that turned the landmark into what Kimmel called a big green slop hole. Recent photos showed dark liquid filling the pool while tarps covered other areas. Kimmel joked that perhaps Trump was pumping the structure with Diet Coke instead of water. How are we supposed to win a war against Iran when we cannot even win the war against algae for God's sake?

The host then stunned the crowd with a joke about Natalie Harp. She is thirty-five years old and serves as one of Trump's top personal aides. Her intimate handwritten letters to the president were recently revealed in the media. One note read, You are all that matters to me. Kimmel asked if a president with historically low popularity numbers would play golf instead of working over the weekend. I do not know, would Natalie Harp drive a golf cart in high heels? You bet your chicken tenders they would. An image flashed behind him showing Harp driving that very golf cart while wearing her shoes.

Fuel prices hit an all-time high on Friday this week. The Strait of Hormuz remains closed to shipping traffic. At this point, Blockbuster Video has a better chance of reopening than the waterway does. Trump declared victory on the first day of the war nearly six-and-a-half months ago. He is now dismissing the ongoing conflict as small potatoes. No one knows more about small potatoes than a man who is built like a sack of wet tater tots, Kimmel added with a laugh.

Tuesday's episode aired just after Labor Day weekend. Kimmel flashed a 2024 post from Trump in which he claimed Americans were suffering through the holiday thanks to Kamala Harris. The president wrote at the time that under Comrade Kamala Harris, all Americans are suffering during this Holiday weekend. He listed high gas prices and rising transportation costs as major issues. Grocery prices were described as being through the roof. Kimmel mocked the irony of Trump complaining about these exact conditions now.

Earlier this week, the Reflecting Pool found itself in yet another mess after powerful storms left debris surrounding the landmark. The situation highlights how regulations or government directives affect the public directly. In response to complaints from Trump, who said We can't keep living under this weak and failed Leadership, Kimmel pointed to gas prices on Labor Day 2024 under Harris. Those prices stood at thirty-three cents per gallon when adjusted for current inflation factors, he noted. He specifically mentioned that the cost was three dollars and thirty-three cents back then.

Gas prices have soared to $4.15 per gallon, marking the steepest Labor Day rates ever recorded in the United States. Jimmy Kimmel addressed this economic reality alongside his take on Donald Trump during his latest broadcast. The host described Trump as 'crazier than ever,' citing a relentless stream of artificial intelligence-generated images flooding social media feeds and noting that Trump managed to post 37 times in a single Sunday alone.

The monologue turned heated before concluding with a compilation video Kimmel labeled the best and worst moments from Trump's summer of 2026. That segment set the stage for the main show, which aired against a backdrop of shocking news regarding the future of late-night television. Page Six reports that Jimmy Kimmel Live is reportedly ending in 2027 after decades on air.

An insider told the publication: 'His contract is not getting extended.' This comes just a year after Kimmel was famously suspended by ABC. However, a spokesperson for ABC Entertainment issued a statement to the Daily Mail denying these claims. They said: 'This information is inaccurate - any reports about the future of the show at this point are purely speculative.'

Insiders suggest new Disney CEO Josh D'Amaro remains unfazed by pressure from Trump and his supporters. One source claimed, 'He's not afraid of the administration… Josh isn't folding.' Another ABC insider insisted that cost-cutting measures were likely the true driver behind the decision to drop the contract. They stated: 'It wouldn't have anything to do with Trump.'

Reports indicate D'Amaro is also offering early-retirement packages to executives as part of a broader restructuring effort aimed at slashing costs across the company. While some whispered that years of Kimmel's criticism might play a role, insiders told Page Six those accusations are unlikely behind the reported decision. The host was pictured following his suspension alongside protestors who showed their support for him.