Donald Trump’s son-in-law, who has been informally advising the business mogul, has contributed more than $100,000 to Democratic campaigns and committees over two decades.

Jared Kushner, husband of Ivanka Trump, has become one of Donald Trump’s "very few" advisers in his campaign to secure the Republican nomination for president, Reuters reported this week. Kushner does not hold an official role in the campaign but helped organize Trump’s closed-door meeting with several Republican lawmakers and party heavyweights on March 21.

Trump’s unofficial adviser has a history of financing Democratic causes, contributing $101,950 to Democratic campaigns and committees since 1999, according to a review of Federal Election Commission records. Kushner, a real estate investor and newspaper owner, has contributed to committees supporting various Democratic politicians, including those that have been friendly to President Obama’s executive actions on immigration reform.

Kushner contributed $2,000 to Hillary Clinton’s 2000 campaign for U.S. Senate in New York and later contributed $4,000 to the committee supporting then-Sen. Clinton in 2003. Clinton, now a Democratic presidential candidate, is likely to be Trump’s foe in the general election should he capture the Republican nomination.

Recipients of Kushner’s contributions also include Sens. Chuck Schumer (D., N.Y.) and Robert Menendez (D., N.J.), both of whom were members of the so-called Gang of Eight pushing for congressional legislation on immigration reform in 2013. Sen. Jeff Sessions (R., Ala.), a prominent Trump supporter, was a leading critic of the immigration bill, which he argued paved the path for "amnesty." Sessions has dredged up his opposition to the bill during the current presidential race to slam Sen. Marco Rubio (R., Fla.), a former GOP presidential candidate who was also a member of the Gang of Eight.

A Trump campaign spokesperson confirmed to Reuters that Kushner had a hand in Trump’s meeting with Sessions and other Republican lawmakers last month.

Kushner has also contributed to the campaigns of Democratic lawmakers who cheered Obama for granting temporary legal status to millions of illegal immigrants in November 2014, an executive action that has been put on hold pending a ruling from the Supreme Court.

Kushner has donated to Sen. Cory Booker (D., N.J.) and Rep. Bill Pascrell (D., N.J.), both of whom celebrated the controversial executive order as encouraging, productive, and necessary.

"I applaud the president’s decision to take action within his legal authority to help address our broken immigration system," Pascrell said in a statement.

"This is an important first step and more needs to be done," Booker said in 2014. "The president’s plan will greatly help law enforcement focus on felons and threats to our country, and pull individuals out of the shadows, not to grant them amnesty, but allow them to pay taxes and start on a path towards lawful immigration."

Kushner’s donations could pose a problem for Trump, who has made his stance on immigration a cornerstone of his presidential campaign. Trump has pledged to build a wall at the southern border with Mexico and expel the estimated 11 million immigrants currently living illegally in the United States.

The lone Republican recipient of Kushner’s money was former New York City Mayor Rudy Giuliani. Kushner contributed $1,000 to an exploratory committee for Giuliani’s U.S. Senate bid in 1999, FEC records show.

Trump has himself contributed to Democratic committees in the past, including committees associated with Clinton, Menendez, Schumer, and Senate Minority Leader Harry Reid (D., Nev.). Trump also donated to the Bill, Hillary, and Chelsea Clinton Foundation, which he has said drew the Clintons to his 2005 wedding. The business mogul only ramped up his donations to Republican groups and candidates in the last five years.

A spokesperson for the Trump campaign did not respond to a request for comment about Kushner’s donations to Democrats.

Kushner made the contributions under a number of different companies that are associated with Kushner Companies, where Jared works as chief executive. The real estate and development company was started by Charles Kushner, Jared’s father, who is a multimillionaire Democratic donor.

Charles Kushner was sentenced in New Jersey federal court to two years in prison for tax evasion, witness tampering, and making illegal campaign donations in 2005. The FEC also fined Kushner over $500,000 for making the illegal campaign donations.