Should You Talk to the Enemy?

Should a party leader communicate with the other political party at a time of great discord and division? Can Democrats collaborate with Republicans for the good of the country? Can they talk to the enemy and succeed?

These questions would, in earlier times, seem obvious. House Members and Senators of both parties talked to one another all the time. They collaborated on bills, traded favors to get their their bills passed, ate together, sometimes socialized, and played golf with one another. Everyone understood that talking to the enemy was simply how they got things done.

Of course, back then we didn’t consider members of the opposite party to be the enemy. They were simply the opposite party, whether minority or majority party, part of the electoral wheel that would inevitably turn and turn again.

When the Cold War Ended

Checkpoint Charlie, Berlin Wall, Cold War, talk to the enemy

Checkpoint Charlie today

That all changed oddly enough when the Berlin Wall fell and the Cold War ended. When our clearly defined enemy went away, Republicans looked around for another enemy. In these days before Islamic terrorism and with 9/11 unimaginable, they turned to Democrats.

Ronald Reagan shepherded repeal of the Fairness Doctrine in 1987 and ushered in Rupert Murdoch’s empire of lies and propaganda. Together, they created propaganda declaring Democrats to be not only the enemy, but evil demons. Many Americans believe this today. Later, Donald Trump jumped eagerly the bandwagon, setting one side against the other and creating deep divisions in the country.

Year by year, the two sides pulled further and further apart. They stopped talking and cooperating. Votes in Congress that favored one side were approved unanimously while the other side voted Nay. After January 6, decorum went out the window to be replaced by acrimony and insult.

Carville Says Don’t Talk to the Enemy

Jared Kushner, Hakeem Jeffries, talk to the enemy

Jared Kushner and Hakeem Jeffries

Now we are treated to the picture of Congressman Hakeem Jeffries talking to Jared Kushner. I reacted with as much shock and outrage as James Carville did. This was not members of two different parties communicating about the common good. It was betrayal, concession, weakness.

In The Daily Beast, Mr. Carville said:

“Hakeem, you’re a smart guy … let me explain something here—very, very clear. You have Democrats that have a different position on Medicare for All, whether that’s a good idea. You have Democrats that have different positions on effective policing, and there’s a whole variety of subjects of which there are some disagreements within the Democratic Party,” he began.

“On one thing, there is no disagreement. There’s unanimity. And it is simply this. In the opinion of every Democrat in the United States—progressive, moderate, middle road, left, f–k, I don’t know, whatever you want—we believe one thing above all: These people are a pack of felons and traitors and you do not meet with them. You do not meet with them!”

“A better alternative would be to drag his a– before a committee and find [out] about what backdoor-dealing whorehouse s–t he’s got going on with Steve Witkoff and everybody else,” Carville added, referring to Kushner’s partner in foreign policy negotiations. “They’re making every backdoor bull—t deal they can. And we don’t meet with them. Don’t meet with them.”

You can’t get any clearer statement than that and it’s shared by many, including me.

Bill Maher Says Always Talk to the Enemy

In April 2025, Comedian Bill Maher, who delights in skewering both sides but caucuses with the Democrats, famously met with President Donald Trump.

Mr. Maher described a dinner with Trump arranged by musician Kid Rock, He told his audience he never felt the need to “walk on eggshells” around Trump, contrasting it with how he would never feel comfortable talking to Democratic presidents in the same way.

Watch Bill’s monologue: Mr. Maher Goes to Washington

He went on to lecture his audience on the importance of speaking with everybody, regardless of what you think of their position or how you feel about them personally. His bottom line is that any communication is better than no communication.

Bill Maher, Donald Trump, Newsweek, talk to the enemy

Bill Maher and Donald Trump (Courtesy of Newsweek)

In general, I agree with him, but I think in today’s political climate communication gives the Republicans an opportunity to put their propaganda inside your head, to use your very presence to demean and disgrace you, and to use whatever you say against you. Communicating with them is playing their game on their terms and you will lose.

For example, Mr. Maher relates how Trump would listen to some hard facts and then smile. He thought that was a good thing. I think it was Trump letting it all roll off his capacious back while he snickered to himself.

I think Mr. Maher went to dinner in good faith and was played by the game-show host and consummate con artist. He got some political credibility but Trump got eleven minutes of good press and nice thoughts.

Hakeem Jeffries Says Wishy-Washy

Given the reaction to the recent unofficial meeting, Mr. Jeffries hastened to say that the presidential son-in-law and envoy without portfolio had called him. Does that make a difference?

What did Jared Kushner tell the Democrat? He said to talk to Susie Wiles, Trump’s Chief of Staff. So, what did that accomplish?

The proverbial crap hit the fan and Mr. Jeffries responded with an interview on CNN. When Wolf Blitzer asked him whether he accomplished anything specific during the meeting with Kushner, Mr. Jeffries replied:

“No, it was just a high-level topical conversation, particularly focused on affordability as well as the housing bill that was recently passed and enacted into law as a foundation for the type of thing that perhaps can be built upon moving forward…. At the same period of time, as I’ve mentioned, nobody’s getting a pass because we’re determined to make sure, beginning on day one, that we hold every single member of the Trump cartel accountable beginning on day one.”

On X, he stated, “No one from the Trump Cartel is getting a pass. We’re going to follow the facts, apply the law, and be guided by the Constitution beginning on day one. And hold the crooks accountable.”

Make of that what you will. I think when you operate from a position of facts, law, and the Constitution, you had better be talking to someone who holds the same values. With the Republicans, however, he’s deluding himself.

Should You Talk to the Enemy?

So should you talk to the enemy? I think it depends on four things:

  1. Who the enemy is.
  2. What you want to get from it.
  3. Whether the enemy is communicating in good faith.
  4. Whether the enemy is better at this than you are.

Rick Wilson made excellent points in his blog post: “ Why I Took On The Kushner-Jeffries Dsaster.”

“Trump has told us, out loud, what cooperation costs; he gets more power, and the sucker who took the deal gets humiliated. He gets no oversight of his venality, his criminality, and his roaring incompetence, and a free pass to keep up his spree of scams, bribes, and grifts. You get humiliation, and ownership of his scandals.”

Rick Wilson, TMZ

Rick Wilson (Courtesy of TMZ)

Mr. Jeffries was dealing with a man who holds good faith in contempt. In Mr. Wilson’s words, “You are dealing with a criminal enterprise that holds the executive branch.” My shock came from realizing that the Minority Leader still doesn’t understand that.

Should you talk to the enemy? It’s your choice; but be careful. No one wants to end up getting played or being a con artist’s mark as Mr. Jeffries just was. I give Mr. Wilson the final word:

“But because in the rules of every deal with the Devil, the Devil always cheats, always lies, and always laughs at the suckers who took the deal.”

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About Aline Kaplan

Aline Kaplan is a published author, a blogger, and a tour guide in Boston. She formerly had a career as a high-tech marketing and communications director. Aline writes and edits The Next Phase Blog, a social commentary blog that appears multiple times a week at aknextphase.com. She has published over 1,000 posts on a variety of subjects, from Boston history to science fiction movies, astronomical events to art museums. Under the name Aline Boucher Kaplan, she has had two science fiction novels (Khyren and World Spirits) published by Baen Books. Her short stories have appeared in anthologies published in the United States, Ireland, and Australia. She is a graduate of Northeastern University in Boston and lives in Hudson, MA.

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