Democratic members of the House Oversight Committee on Wednesday released new emails from Jeffrey Epstein in which he discussed Donald Trump , pushing the issue of their relationship back into the spotlight.

The emails, a selection from thousands of documents turned over by Epstein’s estate to Congress, include a 2011 exchange between Epstein and his longtime associate Ghislaine Maxwell, long before Trump was elected president and years after Epstein and Trump had falling out, as well as messages with journalist Michael Wolff in 2019 while Trump was in the Oval Office.

In the April 2, 2011 email, Epstein wrote to Maxwell: “I want you to realize that that dog that hasn’t barked is trump.. [Redacted name] spent hours at my house with him ,, he has never once been mentioned. police chief. etc. im 75 % there.”

Maxwell responded that same day: “I’ve been thinking about that.”

It’s unclear when Epstein was claiming that Trump spent the time at his house. Maxwell told Justice Department officials this year in a prison interview that she never witnessed Trump behaving inappropriately.

White House spokespeople didn’t immediately respond to requests for comment.

Trump has said he cut off ties long before Epstein was first arrested in 2006. Epstein pleaded guilty to soliciting a minor for prostitution in 2008. Trump and Epstein socialized together in the 1990s and early 2000s. Trump took several trips on Epstein’s private jet in the 1990s, according to flight logs, and told New York magazine in 2002 that “he’s a lot of fun to be with.”

The new batch of emails were released by Oversight Committee ranking member Rep. Robert Garcia (D., Calif.) on the same day that the House is returning to work after more than a month on break.

The House Democrats said they redacted the names of Epstein’s victims in the documents made public Wednesday as well as personal email addresses.

A new Democratic member who won a special election in September, Adelita Grijalva, is set to be sworn in Wednesday, and she is expected to provide the critical 218th signature to force a House vote on releasing files from the government’s investigation into Epstein, or so-called Epstein files. GOP leaders have argued the Oversight Committee is making progress in its investigation and there is no need for a separate vote.

Rep. James Comer, (R., Ky.) the chair of the Oversight Committee, didn’t immediately respond to a request for comment.

The Oversight Committee opened its probe after the Justice Department announced in July not to release more of the files, saying it found no evidence that would lead to an investigation of uncharged third parties and no additional documents that merited public disclosure.

In May, Justice Department officials had informed Trump that his name was in the Epstein files , The Wall Street Journal reported. Trump was told that many other high-profile figures were also named. Being mentioned in the files isn’t an indication of wrongdoing.

Republicans and Democrats on the Oversight Committee have been releasing some materials turned over by Epstein’s estate, including a 2003 birthday book and schedules detailing Epstein’s meetings with politicians and businesspeople.

In a January 2019 email released Wednesday, Epstein wrote to Wolff: “trump said he asked me to resign, never a member ever. . of course he knew about the girls as he asked ghislaine to stop.”

Wolff didn’t immediately respond to a request for comment.

When Epstein was arrested in July 2019, Trump said he had had a falling-out with Epstein and hadn’t talked to him in about 15 years. A White House spokeswoman said at the time that Trump had banned Epstein from his Mar-a-Lago club.

This year, Trump has elaborated on their disagreement and said he banned Epstein from his club because “he was a creep.” In July, Trump told reporters he cut ties because Epstein had poached staffers from Mar-a-Lago and one of those people was likely Virginia Giuffre, a teenage spa attendant.

Giuffre, who died by suicide earlier this year, was one of Epstein’s most prominent accusers. Her family said she was recruited by Maxwell from Mar-a-Lago in 2000 when she was 16. Giuffre accused Epstein of trafficking her to other men. Giuffre said in a 2016 deposition that she never saw Trump participate in any abuse.

Maxwell was convicted in 2021 and sentenced to 20 years for her role in Epstein’s sex-trafficking. Earlier this year in an interview with Deputy Attorney General Todd Blanche, Maxwell said that she “never witnessed the President in any inappropriate setting in any way.”

“In the times that I was with him, he was a gentleman in all respects,” Maxwell said. A week after her interview with Blanche, Maxwell was transferred to a minimum security prison camp in Bryan, Texas.

Write to Khadeeja Safdar at khadeeja.safdar@wsj.com and Joe Palazzolo at Joe.Palazzolo@wsj.com