Sherman and Wuerker speak at Cleveland Park Library

Draining the Swamp Politico-Style

Story and photos by James Arvantes

Politico Writer, Cartoonist Provide Insightful, Humorous and Thought-Provoking Perspectives of Trump Presidency

President Trump is one of the most accessible presidents in modern American history, an accessibility driven by his need for approval and affirmation from large, mainstream media outlets.

That was one of many insights provided by Cleveland Park resident Jake Sherman, a senior writer for Politico who addressed the Tuesday Talk Series at the Cleveland Park Library on Feb. 19 with Politico’s Pulitzer Prize-winning cartoonist Matt Wuerker.

Sherman and Wuerker spoke on the topic of Swamp Tales: Covering the Trump Era in Words and Pictures, addressing a capacity crowd of more than 175 people and lacing their remarks with personal anecdotes and examples. In his remarks, Sherman said Trump is “in constant pursuit” of credit and approval from “big, mainstream media.”

“I would venture to guess he has given more interviews to the New York Times than Barrack Obama did in eight years,” said Sherman, co-author of Playbook, Politico’s daily morning newsletter.

Trump speaks with nearly every member of Congress, many of whom have personal access to the president, said Sherman, co-author of a forthcoming book, The Hill to Die On. (The book tells the inside story of Trump’s first two years in office from the perspective of Capitol Hill, starting with Inauguration Day 2017 and concluding with the end of the federal government shutdown in January.)

“The president will say, ‘just call the White House switchboard,’ which sounds like a throwaway line,” said Sherman, who is also a contributor to MSNBC.

But it is not a throwaway line.

“If you are a reporter or a member of Congress, and you call the White House switch board, I would say there is a better than even chance you are going to get on the line with the president,” he said.

Shortly after the 2016 election, Sherman and his Playbook writing partner, Anna Palmer, met with Trump aides at Trump Tower in New York to try to discern how then President-elect Trump planned to govern. At the end of the interview, Sherman asked Hope Hicks, who was then Trump’s communications director, if he and Palmer could talk to the president-elect.

Hicks responded by saying, “let me look into it.”

“That in and of itself is so strange because usually someone who is on the brink of taking control of the most important country on planet Earth would not be taking visitors from an inside the beltway publication,” Sherman explained.

Hicks, however, took Sherman and Palmer to Trump’s office on the 26th floor of Trump Tower where they met the soon-to-be president. The first thing Trump said to Sherman was, “I recognize you from MSNBC.”

“I thought to myself, how strange is this, that this guy, on the brink of taking power, recognizes me,” said Sherman.

More recently, Sherman and Palmer, co-author of The Hill to Die On, sat down with Trump and interviewed him for more than one hour for their upcoming book.

“He had only met me once, and I did not tell him what I was going to ask him about,” explained Sherman. “To sit down with two journalists for an hour for a no-hold’s bar interview about his experiences as president is relatively stunning and unprecedented.”

Down the Rabbit Hole

Sherman, like many others, describes Trump as an “ideological black hole on huge issues,” saying, “he has a tendency to describe his position on an issue and then act in the complete opposite way minutes later.” He has done this on immigration, gun control and health care.

Trump, for example, called up a reporter from the Washington Post, and told him he wanted a health care plan that covered everyone, a direct contradiction of his earlier statements on health care.

Sherman decried Trump’s constant diatribes against the media, saying his words “put reporters in danger” in this country and abroad.

“It is scary and not productive,” said Sherman. “(Trump) is clearly not going to change.”

Yet, Trump expressed “sorrow and anger” to the publisher of the New York Times about the hostility toward journalists, further evidence of his contradictions, according to Sherman.

“That leaves you wondering,” he said.

Nevertheless, Sherman said, “we are living in a time clearly without historical parallel and for a journalist it is one of the best times to have this job.”

Wuerker elaborated on that theme, saying, “Trump is a gift to cartoonists.”

Matt Wuerker at Cleveland Park Library

“You can put his hair on anything – a train, a fish, whatever – and it is instantly identifiable,” said Wuerker, prompting laughter from the audience.


Wuerker, who won the 2012 Pulitzer Prize for Editorial Cartooning, showed some of his award-winning political cartoons, demonstrating how he uses metaphors and caricatures to create compelling and enduring images.

“I usually have a couple of cartoon ideas when I got to work,” said Wuerker, who won the 2010 Herblock Prize at the Library of Congress as well as the 2010 National Press Foundation’s Berryman Award. “But these days with Trump, there will be half a dozen, and then I will be settling in to draw it and something else will fire up on Twitter or Jake will say something on MSNBC.”

Wuerker has been a cartoonist since the Carter administration 40 years ago — long before the digital age or even the advent of color in newspapers. “We can communicate a simple idea with a visual metaphor,” said Wuerker, a founding staff member of Politico. “Ideally, it is something that has some trenchant insight. But it also can be funny or fun.”

There are times when Wuerker can merge the past with the present in his work. In one cartoon, Wuerker drew Nixon, and compared him to Trump by giving the 37th president access to Twitter. He conjectured what the former president would likely tweet during the Watergate era – a la Trump– such as “lying John Dean doesn’t know what he is talking about” and “biggest witch hunt in history, sad.”

“Any day a cartoonist gets to draw Richard Nixon is a really good day,” he said.

The work of political cartoonists lived in the pages of major newspapers for 150 years, but now, as more and more major newspapers disappear, cartoonists are migrating to social media.

“It used to be that if you wanted to be a political cartoonist and put yourself out there, you had to convince a newspaper publisher to give you a job,” said Wuerker during the question and answer segment of the event.  “There is no barrier to entrance now. If you are a good cartoonist, you can create a community very easily, so the range and impact of cartooning has never been greater.”

But at the same time, it is harder to make a living as a cartoonist, Wuerker said.

“The internet is fundamentally a visual medium,” said Wuerker. “It is a perfect playground for cartoonists. The trick is — how do you turn it into income?”

For another take on this Talk, check out 8-year-old Orly’s blog.

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