Top Ten Funniest Moments of Trump’s Second Term Part II

Governing is serious business, and Americans expect sober-minded and businesslike leaders – particularly during times of military conflict and economic strife. President Donald Trump has long been a master of understanding the gravity of every situation and choosing a tone that meets whatever the moment calls for.

At the same time, Trump has never lost his knack for being an entertainer. Like few leaders before him, he understands that well-timed humor can be just as effective as a stern rebuke. He has also delivered several unintentionally hilarious moments that left his supporters in stitches and his opponents begrudgingly smiling.

Last year, AMAC Newsline published the “Top Ten Funniest Moments of Trump’s Second Term So Far.” Here’s part II.

• Trump Trolls Schumer and Jeffries with “Trump 2028” Hats

One of the left’s favorite lies about Trump is that he’s an authoritarian dictator hell-bent on ripping up the Constitution and installing himself for a third term in 2028.

During an Oval Office meeting with Senate Minority Leader Chuck Schumer and House Minority Leader Hakeem Jeffries last October, Trump decided to have some fun with that by placing “Trump 2028” hats on the Resolute Desk across from the two Democrats. The image quickly went viral online, and Trump succeeded in using humor to point out how ridiculous Democrats’ line of attack is.

• Trump blasts Obama’s presidential library

Late last year, images began circulating online showing construction of Barack Obama’s presidential library in Chicago – a bizarre brutalist monstrosity that left even some Obama fans scratching their heads. Trump, never one to miss an opportunity to snipe at his longtime rival, didn’t mince words when asked about it.

“He needs help,” Trump said. “Yeah, not pretty. He wanted only women and DEI to build it. That’s what he got.”

• Trump adds his special touch to Presidential Walk of Fame

Last September, Trump unveiled a “Presidential Walk of Fame” along the West Colonnade of the White House featuring portraits of every president. In his first jab using the display, Trump swapped out Biden’s photo with a picture of an autopen.

But Trump wasn’t done there. Just before Christmas, he also installed plaques under each photo – with some personal notes on a few select presidents. Obama’s plaque, for instance, reads in part, “spied on the 2016 campaign of Donald J. Trump.” Ronald Reagan’s reads, “Was a fan of President Donald J. Trump long before President Trump’s historic run for the White House. Likewise, President Trump was a fan of his!” Most amusing of all, Bill Clinton’s plaque reads, “In 2016, President Clinton’s wife, Hillary, lost the Presidency to President Donald J. Trump.”

• Trump says the Abrams tank is named after Stacey Abrams

During a speech at Fort Bragg in North Carolina earlier this year, Trump hilariously suggested that the Abrams tank is named after Stacey Abrams, the failed Georgia gubernatorial nominee who refused to concede the election. The comment drew roars of laughter from the audience.

• Trump says he watches for missiles while flying

In perhaps one of the most hilarious off-the-cuff remarks ever delivered by a president, Trump told the National Prayer Breakfast in February that he doesn’t like sleeping on planes because “I like looking out the window for missiles and enemies.” Trump famously engages staffers in wide-ranging discussions on flights, with some officials even admitting that they struggle to keep up with the energetic president.

• Trump roasts Newsom’s terrible interview

During an interview in March, California Governor Gavin Newsom – a frontrunner for the Democrat presidential nomination in 2028 – bizarrely stated that he has learning disabilities right after telling the predominantly black crowd that he’s “just like” them because he “can’t read.” Newsom was apparently referring to dyslexia, which he claims he had as a child.

Trump didn’t hold back when asked about it in the Oval Office: “I think it was the worst interview of any human being I’ve ever seen in my life.” Even the liberal media reporters in the room struggled to contain their laughter.

• Trump reminds the Japanese Prime Minister that they like surprises

During a White House meeting with Japanese Prime Minister Sanae Takaichi in March, Trump couldn’t resist the opportunity to offer a little jab after a reporter asked him why he didn’t tell U.S. allies before attacking Iran.

“We wanted surprise,” Trump said. “Who knows better about surprise than Japan? Why didn’t you tell me about Pearl Harbor?” Although the remark led to plenty of pearl-clutching on the left, most Americans with a sense of humor had a good chuckle.

• Trump tells Mamdani to just call him a fascist

The first Oval Office meeting between Trump and New York City Mayor Zohran Mamdani wasn’t expected to produce any funny exchanges, but Trump delivered again when a reporter tried to make things awkward by asking Mamdani if he thought Trump was a fascist.

“That’s ok, you can just say yes,” Trump said, patting Mamdani’s arm with a wry smile. “It’s easier than explaining it. I don’t mind.”

The comment perfectly channeled the exasperation that Trump and so many other Americans feel toward the media’s constant efforts to brand the President as a fascist. Instead of becoming angry or defensive, Trump used humor to neutralize the attack and make the reporter look foolish.

• Trump asks when the statue of him is going up in Venezuela

During a cabinet meeting earlier this year, Secretary of the Interior Doug Burgum joked that Venezuela is going to put up a statue of Trump to thank him for removing Nicolas Maduro from power. A full two minutes later, Burgum was wrapping up an update on Venezuelan oil flowing to U.S. refineries, and Trump saw his opportunity for a quick bit of humor.

“Forget that – when are they going to do the statue?” he asked. The room immediately erupted in laughter, and the clip quickly went viral on social media.

• Trump riffing on how much he likes Sharpies

Unlike past presidents who signed documents with expensive pens, Trump has opted for his iconic “big Sharpie.” During a cabinet meeting, he offered some unintentionally hysterical insight into why he made that choice.

“You see this pen right here? This pen is very inexpensive,” Trump said, holding up the Sharpie for the reporters gathered in the room. “But it writes well. I like it. Sharpie. I came here. They had $1,000 pens. You hand out pens. You hand them to people. 30, 40 people. They were $1,000 apiece. Beautiful pen, ballpoint. I hand out to kids that don’t know. It’s a kid getting a pen for $1,000. They have no idea what it is.”

In addition to being undeniably funny, Trump was also making a broader point about waste in the government. Instead of $1,000 pens, he made the switch to inexpensive Sharpies which actually do a better job.

There will undoubtedly be many more humorous moments throughout the rest of Trump’s term, and AMAC Newsline will be here to cover them all.

In the meantime, you can also check out Part I and Part II of our “Top Ten Times Team Trump Has Owned the Media” series.

Shane Harris is the Editor-in-Chief of AMAC Newsline. You can follow him on X @shaneharris513.