Former Trump campaign aide Rick Gates pleaded guilty Friday to conspiracy against the U.S. and to lying to the FBI in the biggest score so far for special counsel Robert Mueller’s investigation.

Gates entered his plea in U.S. District Court for the District of Columbia. He was a top aide to Paul Manafort, a onetime campaign chief for candidate Donald Trump.

During the 2016 campaign, Gates worked to help Mr. Trump win the Republican presidential nomination by brokering deals with Republican delegates. He was also a member of Mr. Trump’s inaugural committee and worked with pro-Trump political groups, including American First Action and America First Policies.

According to a new indictment filed Friday, Gates and Mr. Manafort made tens of millions of dollars working on behalf of Ukrainian government interests, then shielded much of that money in accounts in Cyprus, the Seychelles and other places to avoid federal tax obligations.

The two men handled more than $75 million, with Mr. Gates laundering more than $3 million for himself and Mr. Manafort laundering more than $18 million, prosecutors said.

When investigators began probing, Gates and Mr. Manafort also lied to them, the special counsel says.

The illegal lobbying took place from 2006 to 2014, prosecutors said. That puts the activity before the time when Mr. Manafort was Mr. Trump’s campaign honcho, and Gates was a top aide.

Both Gates and Mr. Manafort had entered “not guilty” pleas earlier, and Gates’ change suggests the special counsel is closing in on Mr. Manafort.

Mr. Manafort continued to maintain his innocence in a statement Friday.

“I had hoped and expected my business colleague would have had the strength to continue the battle to prove our innocence. For reasons yet to surface he chose to do otherwise,” Mr. Manafort said. “This does not alter my commitment to defend myself against the untrue piled up charges contained in the indictments against me.”

Gates could face as much as five years in prison for each charge, but that could be reduced to based on possible cooperation with the special counsel.

U.S. District Judge Amy Berman Jackson did not schedule a sentencing date, but a status report will be presented to the court on May 14.

On Friday, Gates also filed court documents requesting the judge’s permission to travel with his children to Boston this spring so “they can learn about American history in general and the Revolutionary War, in particular.”

Gates’ guilty plea came one day after a second indictment added 32 new against him and Mr. Manafort, including bank fraud and filing false tax returns. The two were alleged to have used income funneled through offshore bank accounts in Cyprus and other locations, while acting as foreign agents for the Ukraine and fraudulently obtaining bank loans.

Prosecutors allege that Gates spent the loans on his mortgage, children’s tuition and decorating his Virginia house. Mr. Manafort used the money to enjoy a “lavish lifestyle” in the United States, prosecutors said.

Mr. Mueller has been filing indictments at a rapid pace lately. This month he charged 13 Russians and three Russian internet agencies with conspiracy to disrupt the 2016 presidential election through a social media disinformation campaign.

On Tuesday, he indicted Dutch attorney Alex van der Zwaan with lying about his interaction with Gates. The attorney had worked with Gates and Mr. Manafort on a report justifying the jailing of former Ukrainian Prime Minister Yulia Tymoshenko.

⦁ Dave Boyer contributed to this report.

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