Remember that line from The Dark Knight about how people either die a hero or live long enough to see themselves become the villain? Well, that seems to be an accurate summary of many political careers, and especially the career of Nancy Pelosi. She’s been in politics so long that she has gone from being primarily demonized by Republicans to being a favored target of younger Democrats who would like to replace this establishment politician with someone else.
As someone who has made so many enemies over the years, Pelosi has worked hard to control her images over the years, meaning there aren’t that many embarrassing photos of her floating around. But that didn’t keep us from rounding up this collection of photos that Pelosi definitely never wanted you to see.
What are these photos, and what makes them so cringeworthy? Keep reading to find out!
Hanging with JFK
This photo serves as a powerful reminder for how long Nancy Pelosi has been interested in politics. And we can only imagine she sees this photo of the beloved JFK, Jr. before he was assassinated as a bittersweet memory of a happier time.
Meme reaction face
Back in 1990, Pelosi was speaking about H.R. 2712, a bill for which she was the primary sponsor. She may be proud of the bill, but she’s probably not proud of this goofy face that makes for a perfect reaction image that is custom-made for memes.
Another wacky face
Here, we see a 1996 image of Pelosi scrutinizing yet another bill. Reading and discussing bills like this is one of the biggest parts of her job, but that doesn’t change the fact she is rocking her best “what the hell am I reading” face in this image.
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The Bill Clinton years
We can only assume Pelosi has mixed feelings concerning her years of working with Bill Clinton. Those were prosperous days for both the nation and the Clintons, though the Monica Lewinsky controversy ended up casting a wide shadow on everyone involved in this administration.
Taking things a bit too literally
In 2001, Nancy Pelosi was elected as the House Whip. In order to celebrate, she took a goofy picture of herself holding an actual whip, which is about as funny now as it was back then (in other words, not funny at all).
Hanging with her daughter
Nancy Pelosi here is posing with her daughter, filmmaker Alexandra Pelosi, at the premiere of Journeys With George, a documentary focusing on George W. Bush’s successful presidential campaign. While Pelosi is understandably proud of her daughter, we doubt she loved reliving the George W. Bush political years on the big screen.
Mean mugging the president
Speaking of George W. Bush, Nancy Pelosi had to work very closely with him for eight years of his presidency. They seemed to have a very cordial relationship, though in this image, we can practically hear Pelosi thinking “this freaking guy!”
Looking confused and bemused
Some of what Pelosi did with Bush included fun activities such as awarding Congressional Gold Medal to the Dalai Lama. But in this image, it looks like Pelosi is waiting for a movie to freeze before she begins her narration: “you wouldn’t believe how I got myself into this situation.”
Freaking out, man
In 2008, Nancy Pelosi attended the National Italian American Foundation 33rd Anniversary Awards, and it looked like a fun event. But in this image, it looks like Pelosi has just seen something monstrous off to the right, so maybe it was scarier than we thought it would be.
Looking for her own bailout
This is a relatively normal photo of Pelosi discussing the financial crisis bailout back in 2008. But considering how much both the crisis and the bailout would come to define Barack Obama’s presidency, we doubt she wants anyone to focus too much on images from those bad old days.
Nancy meets justice
Here, we see Nancy Pelosi meeting Supreme Court Justices Ruth Bader Ginsburg and Sonia Sotomayor in 2015. It was a big honor at the time, but we have to wonder if Pelosi now shares the belief that RBG should have retired when she had the chance to allow a Democrat president to pick her replacement.
Yass, meme queen
It’s an open secret that Nancy Pelosi really hated Trump (and that he hated her). After Trump’s 2019 State of the Union address, Pelosi gave him a sarcastic clap which likely felt fun in the moment, but this became a moment that political rivals constantly used against her in their later rhetoric.
Letting it rip
At the next year’s State of the Union address, Pelosi one-upped herself by ripping up Trump’s speech in a bit of symbolic rebellion. However, this moment, too, ended up haunting Pelsosi because it gave so much political ammo to her opponents.