Fifteen years ago, I was hired as the staff cartoonist/illustrator for a startup called The Politico.com. It wasn’t clear at first, but a Great Disruption was under way. Our assumption that America was and would always remain the one superpower in the world, our basic faith in the fairness of our free market system, even our shared sense of reality itself all turned out to be on very shaky ground, all amid a digital revolution. American politics was rocked by seismic changes, jolted and tested by tectonic shifts.

Over these past 15 years, POLITICO has done its best to keep up with all the disruption and tumult. Throughout, I’ve been lucky to find myself with a front-row seat — well, actually a back-corner-of-the-newsroom seat — to try my best to capture and comment on all the changes and characters, from Sarah Palin and Bernie Sanders to Barack Obama and The Donald, of course, whose hair alone was perhaps the greatest gift to cartoonists ever.

So, with the caveat that it is impossible to sum up a 15-year period in politics in a couple dozen cartoons, here’s an attempt, in broad strokes, to chronicle an indeed epic epoch from the vantage point of my catbird seat here at POLITICO. (I hasten to add that in the long tradition of Thomas Nast, Herblock and others, these cartoons are entirely the opinion of the cartoonist — me — and not the editorial views of POLITICO.)

JAN. 23, 2007

You might ask why a disruptive, forward-thinking news outfit would look backward and decide to include an editorial cartoonist in the crew at the launch, much less why they’d keep the ink-stained wretch on board for the rest of the voyage. I can offer my assumptions: The first is that, in the beginning, it was handy to have a scribbler like me around to fill column inches with illustrations, caricatures and the like, as we stumbled our way toward print deadlines. The answer to my achieving tenure on the crew I believe has to do with the lasting power of this 18th-century form of art and rhetoric: Cartoons are juicy yet easily digestible nuggets of political commentary, not to mention they are also well-suited to our very visual digital age.

My first cartoon for the first edition of The Politico was a purely pen and ink effort, but on Day 2, we went full color and I got to pull out my watercolors!

MARCH 20, 2007

A colorful turn of phrase can offer a perfect peg on which a cartoonist can hang an entire cartoon — or even two. Four years after the Bush administration launched its disastrous response to the 9/11 attacks, the “cakewalk” one Bush ally had promised descended into chaos.

JAN. 29, 2008

It’s not just the bon mots that come out of the mouths of politicos but also the handiwork of their PR teams that can often serve up juicy meatballs for cartoonists and satirists. One of the juiciest of all time was when President George W. Bush appeared in his flight suit in front of the “Mission Accomplished” banner. If the trope fits, wear it, and Bush did — right through to the end of his term. After eight years in office, the economy was cratering; the War on Terrorism had turned into a hopeless, bloody morass; and old-school conservatism had been driven into a ditch. So as Bush headed for the exits with his usual swagger, I put him back in his flight suit.

MAY 15, 2008

Cartoonists love a familiar face. The election of 2008 was all teed up for Hillary Clinton, which made the cartoonists happy. Hers was a face that had already launched a thousand cartoons. But along came a young first-term senator from Illinois who had a new way of working with and mixing the politics of color — Black, white, red state, blue state.

A new caricature always challenges cartoonists. Barack Obama, a new face and the would-be first Black president, posed the extra challenge of keeping well clear of what lamentably is a long tradition of racist stereotyping in cartoons. Fortunately, Obama was fun to caricature: His big ears and megawatt smile gave us plenty to work with.

SEPT. 27, 2008

As the 2008 campaign was heading into fall, so was Wall St., and it turned out to be a big fall. Faced with another economic depression, the free marketeers forgot all about their “government is the problem” talk and instead begged the government to bail them out. Once again, Uncle Sam had to come to the rescue.

NOV. 5, 2008

In 2008, the GOP reached deep down the bench and came up with a stunning running mate for John McCain: Sarah Palin. Her brash, in-your-face style roused the Republican rabble and would unleash something we all first called the Tea Party. Tapping into racial and economic anxieties and a deep resentment of Washington elites, the Tea Party didn’t succeed in stopping the rise of Obama, but it would succeed in transforming and taking over the Republican Party.

JAN. 8, 2009

Obama made history as the country’s first Black president, and the GOP vowed to do everything it could to make him history. The dog whistlers pulled out all their stops from the get go, while party leaders did their best to paint Obama in the reddest red-baiting red.

My favorite cartoons are the ones with the fewest words. A crisp visual lampoon has special powers. I also find that brainstorming on my bike ride into work is often very fruitful, so I was very happy when it occurred to me, as I pedaled over the Key Bridge to POLITICO’s Rosslyn office one day, how with just a few little tweaks the famous Obama “CHANGE” poster could be turned into the iconic Che Guevara poster. It pretty much summed up the way Obama’s opponents wanted to portray him when he took up residence in the White House.

JUNE 7, 2009

Cartoon ideas can come from all sorts of places: Something someone says in passing, or a random headline or tweet can spark an idea. Sometimes, they’re suggested by a friend. Jerry Fritz, POLITICO’s lawyer at the time, dropped by my desk, something he often did, at the beginning of the Obama years. The administration was focusing its energies on trying to fix our broken health care system. Jerry suggested it was like someone diving into an empty pool. I played around with the idea and realized how one viewed someone taking a dangerous dive like that depended very much on how one viewed the talent of the diver — and whether you wanted him to succeed.

SEPT. 23, 2009

Like most of our economic history, the rebound to the Great Recession greatly favored the upper decks. Over the last 15 years, we’ve witnessed a staggering concentration of wealth at the top, which is a metaphor ripe for visualization.

JULY 21, 2010

By 2010, the media was starting to undergo a fundamental change. It may be true that we have nothing to fear but fear itself, but the media seemed to find that nothing is more entrancing than fear itself. We gravitated to a new kind of news that favored fear mongering over facts. Cable “news” especially was serving up a hi-def tribalism that aimed to cater to whatever bias the viewer wanted confirmed. Polarization went prime time.

SEPT. 16, 2010

The Tea Party was out to do more than just rock the boat. The 2010 midterms brought a massive red tide and swept the Tea Party into Congress. Obama and the Dems got a thumping as did the old-line Republicans.

AUG. 31, 2011

Nearly three years after taking office and promising to close Guantanamo, Obama couldn’t seem to escape the Bush/Cheney legacy of torture and human rights abuses. The post-9/11 national security state ballooned in both Republican and Democratic administrations. A new era of targeted drone attacks that recognize no borders, extrajudicial renditions and black sites have changed the way we fight our wars. There was no getting out of Cheneytown.

MAY 3, 2012

The Supreme Court’s Citizens United decision of 2010 did more than cement the power of money in politics. It made it something that could be wielded covertly. Ironically enough, at the same time, efforts to suppress the vote were focusing on voter I.D. issues. It became harder to participate in an election than to buy one.

AUG. 6, 2012

Partly due to the ruling in Citizens United, the campaign of 2012 was a muddy, dark-money fest. PACs were now competing with Super PACs for influence. In the end, the most expensive presidential election ever, a phrase that is redeployed every four years, happened in a murky green sea of 7,000,000,000 dollar bills.

MARCH 3, 2013

As the Afghan morass entered its 12th year, the generals and different war strategies came and went while the war lords and defense contractors remained constant. No one could find an honorable exit. Obama, who’d promised to end the war, instead surged troops with yet another new plan to win: a counter-insurgency strategy that only meant he’d be handing the war over to the next president, and, it turned out, the next one after that.

JULY 3, 2013

Six years into the digital revolution Americans had handed reality over to screen time. Smart phones and social media became our constant companions. It became hard to see the forest for the screens.

The upside for cartoonists was the new platforms for our images. They could now be viewed on high resolution, brilliant technicolor displays! When we’d publish our cartoons, they’d show up in people’s pockets, at the speed of light! Then again, the trolls on Twitter and in the comment sections could now fire their retorts back at us — also at the speed of light!

SEPT. 15, 2015

Cue the Trump Show. The GOP found that its angry base wanted a true disruptor. They wanted someone who’d take on those arrogant coastal elites living in their gilded penthouses. So, descending from his gilded penthouse on his golden escalator, Donald J. Trump declared that he, and he alone, could Make America Great Again. And the base went wild.

Early in the primaries Trump demolished his opponents, bullying “low energy” Jeb Bush, “Little Marco” Rubio, “Lyin’ Ted” Cruz and the rest of the field off the stage. Right up to the convention in Cleveland, the party establishment hoped to find a way to derail the Trump train, but it was too late. At the Trump Hotel, you can check in but you can never leave.

MARCH 4, 2016

American politics always had dog whistlers, but it had never seen a dog whistle virtuoso the likes of Trump. Marshaling the base’s “discomfort” with our first Black president along with its hatred of the elites, Trump amplified the old dog whistle by combining it with Twitter. His instantaneous, unhinged and often completely untrue rants were unlike anything ever seen in presidential politics — something that would be said for many things that happened over the following five years.

JULY 14, 2016

Speaking of things that were unlike anything that had ever been seen before, Trump’s hair was a very generous gift to cartoonists. You could skip all the rest of him and just put that singular hair — the mystifying combover, the perfectly straight sidewalls — on anything — a boat, a lizard, even a plant — and you’d caricatured the president!

This homage to Little Shop of Horrors is maybe my favorite cartoon of the last 15 years. It was drawn at the start of the 2016 GOP convention, in which Trump completed his takeover of the Republican Party. The forces the party had unleashed to hamstring Obama — the birtherism, the xenophobia and vitriol — had gotten out of control, and in the end it rose up and devoured the gardener who’d cultivated, fed and watered it.

DEC. 22, 2016

Journalism may be reaching a breaking point. As our eyeballs have wandered away from ink on the page and focused on pixels on screens instead, newspapers have lost readers and their revenue. Traditional journalism may be boring but it’s what holds back the flood of rumor and misinformation (or at least mostly holds them back). A rising tide of unchecked facts and outright BS is overwhelming our shared sense of what’s truth and what’s not.

AUG. 17, 2018

Over the last decade and a half, we’ve seen a lot of fire and rain. Turns out, us humans have put a lot of junk into the atmosphere over the years, and that is radically changing the climate. Up until just a few years ago, many folks still claimed that the science was a hoax, but as the heat and storms have become more catastrophic, it has become undeniable that climate change is the central issue of our time.

APRIL 1, 2020

A bit like Donald Trump’s hair, the Covid-19 virus is very colorful and recognizable. You could even say it’s fun to draw. That’s not much of a silver lining to this horrible pandemic that’s brought so much misery and death, but it did make life for cartoonists a little easier!

The virus showed we were defenseless — despite spending more money on our military than the next 11 countries combined.

JUNE 17, 2020

The murder of George Floyd rocked the conscience of the country. It was a tipping point that not only woke up white America to the reality of police violence perpetrated on people of color today but also to other kinds of violence against the Black population throughout history that we’d done our best to bury. The uprest in cities across the country stirred a massive movement, and a Rip Van Whitey Winkle Uncle Sam had no choice but to awaken from a deep sleep and begin to grapple with the many vestiges of racism.

JUNE 18, 2021

Say what you will about Ronald Reagan’s policies, he had a great mug and was a real pleasure to caricature. Up until recently, Reagan was a Republican God, invoked by many, revered by all. But times have changed. The party base now worships at a new altar.

OCT. 26, 2021

In the first years of POLITICO, some folks bashed us for speeding up and trivializing the news. Don’t blame us! It wasn’t our idea; we were just trying to keep up with the new technologies that keep reshaping media. In those days it was about the digital revolution shrinking attention spans and cranking up the news cycle to dizzying speeds.

Now 15 years on, technology is again revolutionizing how we get our news. These days algorithms, big data and artificial intelligence are curating reality for us. Facebook, the biggest curator of them all, has figured out that what drives engagement is provocation. So Facebook has tuned its algorithms to maximize conflict. What could go wrong?

This is likely not a good thing for humanity — but hey, like many other calamities before, there is always the hope that it’ll generate some epic cartoons.

It’s easy to make oneself look smart and prescient when curating cartoons with the benefit of hindsight. If you want to delve further into my uncurated and more recent scribblings, take a look at my archive page. Also check out our Cartoon Carousel, a weekly gallery of cartoons by other ink-stained wretches that POLITICO publishes every Friday.