Top Senate Democrats are pushing for answers on whether a provision in a controversial settlement agreement between President Trump and his own administration applies to companies co-founded by or affiliated with the Trump family.

As part of a deal struck in May by the Justice Department to resolve a lawsuit brought by Mr. Trump, the Internal Revenue Service is permanently barred from pursuing claims against Mr. Trump, his oldest sons Don Jr. and Eric, and the Trump Organization based on prior tax returns.

In a one-page document signed by Acting Attorney General Todd Blanche and dated May 19, the Justice Department said the defendants in the president’s lawsuit — the IRS and the Treasury Department — are “FOREVER BARRED and PRECLUDED” from “prosecuting or pursuing, any and all claims” arising from tax returns filed before the settlement took effect. Blanche also wrote that the settlement applies to “parties including trusts, parent, sister, or related companies, affiliates, and subsidiaries.”

Now, Senators Elizabeth Warren of Massachusetts, Senate Minority Leader Chuck Schumer of New York, and Ranking Member of the Senate Finance Committee Ron Wyden of Oregon are pushing 11 businesses and organizations with ties to the Trump family to get answers for the “significant questions” the settlement raises relating to the tax audit provision, and whether the companies are included in the deal.

“Under the guise of a so-called legal settlement, the Trump administration has attempted to decree that the President, his family, and their entire business empire — potentially including entities with even the vaguest ‘affiliation’ to the family — are to face zero consequences if they have committed a range of financial crimes or misdeeds — regardless of the severity of the violation,” the senators wrote in letters transmitted to the companies Monday night. 

The letters were sent to mining company Kaz Resources, defense firm Powerus, cryptocurrency companies World Liberty Financial and American Bitcoin, robotics startup Foundation Future Industries, investment firm 1789 Capital, private aviation company Tag Air, and prediction markets Polymarket and Kalshi. 

All of the companies either were founded by Mr. Trump and his two adult sons, or list members of the Trump family as advisers, board members, or partial owners. Donald Trump Jr. sits on Polymarket’s advisory board and 1789 Capital, where he’s a partner, has invested in Polymarket. Days before Mr. Trump took office for his second term, Kalshi also announced Trump Jr. would be a strategic adviser.

The Democrats, who are in the minority, lack subpoena power, so Mr. Trump, his children and his companies can’t be forced to answer the questions posed by the senators.

According to recent financial disclosures, the president earned more than a billion dollars from cryptocurrency ventures alone last year, including from his meme coin business and World Liberty Financial, his family’s cryptocurrency firm. 

Separately, the senators also asked the Trump Organization in a separate letter if it believes it has “immunity from all audits, civil penalties or federal prosecution” for any crimes that could have occurred before the settlement.

Trump Media and Technology Group, which is majority owned by a trust that lists Mr. Trump as the sole beneficiary and operates the Truth Social platform he uses daily, also received a letter from the Democratic senators.

“The public deserves transparency about the scope of this get-out-of-jail free card for Trump-aligned businesses, and about whether you intend to rely on this settlement as a free pass for any possible violations of the law,” the senators continued in their letter, which also seeks any communications that executives at the companies have had with the Justice Department and White House leading up to or after the settlement was signed.

The settlement was announced months after Mr. Trump and two of his sons and the Trump Organization accused the IRS and Treasury Department of unlawfully allowing a government contractor to leak tax returns to media outlets in 2020. 

In a statement, a Justice Department spokesperson said “the IRS routinely provides releases as part of resolving taxpayer reviews and audits. This settlement follows that same standard practice.” 

The spokesperson did not provide specific information about which companies are covered by the audit provision, or whether the Trump Organization and Trump family are the only entities covered by that addendum.