Every Friday I gather a handful of stories that made me stop scrolling, sip my coffee, and stare at the screen for a moment.
This week’s collection features a governor who isn’t running for president until she maybe is, a singer who suddenly discovered politics, Democrats turning on Jill Biden, a proposed Trump bill, a mayoral candidate facing questions about September 11, and Rosie O’Donnell wondering why nobody noticed her facelift.
In other words, another perfectly normal week in America.
Gretchen Whitmer Is Not Running For President. Until Further Notice.
Michigan Governor Gretchen Whitmer announced she would not run for president in 2028.
That’s a pretty impressive campaign strategy.
Step one: announce you’re not running.
Step two: clarify you didn’t actually mean it that way.
Step three: spend the next two years denying you’re running while everybody knows you’re running.
NOW – Michigan Governor Gretchen Whitmer: “My father once said to me, ‘You know, you’d have to be a sociopath to run for president.’ And then about two years ago, he said, ‘You might need to think about running for president.'” pic.twitter.com/ocGMpqARIn
— Disclose.tv (@disclosetv) March 11, 2026
Political reporters call this “keeping options open.” Normal people call it what happens when somebody gets caught peeking at the dessert menu after saying they’re full.
Read more: Washington Post
The $250 Trump Bill
Apparently, Treasury officials have been preparing for the possibility of a $250 bill featuring Donald Trump’s portrait as part of America’s 250th anniversary celebrations.
JUST IN: The Trump administration has reportedly pushed for a new $250 bill featuring Trump’s portrait. pic.twitter.com/4UZuGxpz0A
— Polymarket (@Polymarket) May 28, 2026
I wasn’t expecting a $250 Trump bill to enter the national conversation this week, but here we are.
Honestly, a $250 bill for America’s 250th birthday is at least on theme.
Besides, let’s be honest about what would happen if these things ever hit circulation. Some people would frame them. Some people would collect them. Some people would spend the next six months posting angry rants about them online.
Which, when we’re talking about Donald Trump, is pretty much guaranteed.
Read more: Washington Post
Nancy Pelosi’s Replacement Race
Nancy Pelosi has officially endorsed a candidate in the race to replace her in Congress.
Forty years in Congress and Pelosi still isn’t leaving quietly.
At this point, Pelosi’s political machine feels less like a retirement and more like one of those family businesses where Mom still controls everything from the back office.
Read more: MS Now
Martina McBride Suddenly Discovers Politics
Country singer Martina McBride reportedly dropped out of the Freedom 250 Festival celebrating America’s birthday because she didn’t want to participate in something she viewed as political.
Interesting.
Because apparently performing for Barack Obama was fine. Performing at America’s 250th birthday celebration while Donald Trump is president? Suddenly, that’s political.
Funny how “I don’t do politics” often arrives right around the moment somebody doesn’t like the politics involved.
Amazing coincidence.
Read more: Page Six
Democrats Versus Jill Biden
According to reports, some Democrats are furious about Jill Biden’s upcoming memoir and the continuing questions surrounding Joe Biden’s health.
One quote reportedly suggested she “must have had a stroke herself.” That’s how ugly this family feud is becoming.
NEW: Former First Lady Jill Biden says she thought her husband was having a stroke during his 2024 debate against Donald Trump.
Jill famously boasted on stage with Joe Biden after the debate about how he did “such a great job.”
“I thought, ‘Oh my God, he’s having a stroke,’ and… pic.twitter.com/wfYBoIpxWx
— Collin Rugg (@CollinRugg) May 27, 2026
The same people who spent years telling Americans not to believe their own eyes during the 2024 campaign are now arguing over who knew what and when.
The cover-up story has become more entertaining than the original story.
Read more: New York Post
Zohran Mamdani And September 11
New York mayoral candidate Zohran Mamdani is under scrutiny for boycotting New York City’s Israel Day Parade.
You already know where this is headed.
If he struggles to participate in events supporting America’s closest ally in the Middle East, it raises fair questions about how he intends to handle future commemorations involving terrorism, national security, and September 11.
New Yorkers deserve those answers now because September 11 is not exactly a minor footnote in this city’s history.
Read more: New York Post
Tim Walz Pardons Armed Robber Before Deportation
Minnesota Governor Tim Walz pardoned an illegal immigrant convicted of armed robbery before federal authorities deported him to Laos.
Tim Walz pardons illegal alien convicted of armed robbery before ICE deportation to Laos https://t.co/pQPU23kUbl pic.twitter.com/VH9bk0v0nK
— New York Post (@nypost) May 29, 2026
Every election cycle Democrats insist Republicans are exaggerating concerns about crime and immigration.
Then a story like this drops into the news feed.
And suddenly Republicans don’t have to say anything.
The headline does the work for them.
Read more: New York Post
Rosie O’Donnell’s Facelift Mystery
Rosie O’Donnell says nobody noticed her facelift.
To which I can only ask: isn’t that the opposite of the goal?
If I spent thousands of dollars on a facelift and nobody noticed, I’d be calling customer service.
Read more: Page Six
Final Side-Eye
And that’s this week’s Side-Eye Friday.
The older I get, the less I worry about finding clever commentary because the headlines keep doing most of the work themselves. All that’s left is deciding which story deserves the strongest side-eye.
Until next week, keep the coffee hot and the skepticism healthy.
Feature Image: AI-generated illustration.
