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Trump has repeatedly blasted both Democrats in the past.
Pelosi, the House minority leader, has been in Trump's cross-hairs less frequently than Schumer, the Senate minority leader -- but both have faced the president's ire.
As a fellow New Yorker, Trump has interacted frequently with Schumer through the years, and has even made political contributions to him, according to the Center for Responsive Politics.
But that hasn't stopped the president from taking him to task.
Trump gave Schumer a slew of nicknames, including "Head Clown," "Fake Tears" and "Cryin' Chuck."
Cryin' Chuck Schumer stated recently, "I do not have confidence in him (James Comey) any longer." Then acts so indignant. #draintheswamp— Donald J. Trump (@realDonaldTrump) May 10, 2017
Nancy Pelosi and Fake Tears Chuck Schumer held a rally at the steps of The Supreme Court and mic did not work (a mess)-just like Dem party!— Donald J. Trump (@realDonaldTrump) January 31, 2017
The Democrats, lead by head clown Chuck Schumer, know how bad ObamaCare is and what a mess they are in. Instead of working to fix it, they..— Donald J. Trump (@realDonaldTrump) January 5, 2017
He has also called Schumer a bad leader, not a natural leader, poor leader, and someone who was leading the Democrats to doom.
In spite of those insults, Trump did compare Schumer favorably to former Senate Majority Leader Harry Reid, D-Nev.
"I have always had a good relationship with Chuck Schumer. He is far smarter than Harry R and has the ability to get things done. Good news!" he wrote on Twitter in November after the election.
I have always had a good relationship with Chuck Schumer. He is far smarter than Harry R and has the ability to get things done. Good news!— Donald J. Trump (@realDonaldTrump) November 20, 2016
As for Pelosi, Trump has sarcastically criticized her leadership in one tweet, and linked her with Schumer as a form of insult in another.
"I certainly hope the Democrats do not force Nancy P out. That would be very bad for the Republican Party – and please let Cryin’ Chuck stay!" Trump wrote in a June tweet.
I certainly hope the Democrats do not force Nancy P out. That would be very bad for the Republican Party - and please let Cryin' Chuck stay!— Donald J. Trump (@realDonaldTrump) June 22, 2017
In March, he called for them both to be investigated: "I hereby demand a second investigation, after Schumer, of Pelosi for her close ties to Russia, and lying about it."
I hereby demand a second investigation, after Schumer, of Pelosi for her close ties to Russia, and lying about it. https://t.co/qCDljfF3wN— Donald J. Trump (@realDonaldTrump) March 3, 2017
Tonight's dinner is not the first time that the Democratic pair have made a trip to the White House in recent weeks. The last time they were at 1600 Pennsylvania Avenue, they agreed to a plan to repeal the debt ceiling.
The topics that are reportedly going to be discussed tonight include protections for Dreamers under the Deferred Action for Childhood Arrivals (DACA) program and efforts to stabilize the health care insurance markets, according to sources familiar with the meeting.