Former Secretary of State Hillary Clinton’s youngest brother Tony Rodham died Friday night. The cause of his unexpected death remains unknown.

The former U.S. senator, Secretary of State, first lady, and twice-failed Democratic presidential candidate announced his death Saturday on social media.

At times, Hillary has endured a strained relationship with her two brothers, Tony and Hugh Rodham. The two brothers are best known for their role in a 1999 political scandal involving a controversial international investing scheme, when then-President Bill Clinton’s White House publicly rebuked them.

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On Saturday, Hillary tweeted —

We lost my brother Tony last night. It’s hard to find words, my mind is flooded with memories of him today. When he walked into a room he’d light it up with laughter. He was kind, generous, & a wonderful husband to Megan & father to Zach, Simon, & Fiona. We’ll miss him very much.

— Hillary Clinton (@HillaryClinton) June 8, 2019

Tony Rodham was born in 1954 to parents Hugh and Dorothy Rodham. He was raised in the Chicago suburbs along with his older siblings, Hillary, who is now 71 years old, and Hugh, who is 69.

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The youngest Rodham held a variety of jobs over the years, including stints as a prison guard, insurance salesman, repo man, private detective, and business investor. He attended but never graduated from Iowa Wesleyan College and the University of Arkansas.

It wasn’t always a strained relationship between Hillary and her brothers. While his brother-in-law Bill Clinton was president, Rodham worked on the Democratic National Committee as an outreach coordinator.

He also became one of the few people to ever get married at the White House. He wed Nicole Boxer, the daughter of former U.S. Sen. Barbara Boxer, a California Democrat, in the Rose Garden in 1994.

The couple divorced in 2001. Rodham remarried in 2005.

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But Tony and his brother Hugh were most notable for their connection to at least one scandal in the Clinton administration.

The White House in 1999 had to publicly rebuke the brothers for a business venture in which they planned to export hazelnuts from the former Soviet Republic of Georgia with the help of Aslan Abashidze, the leading political rival of then Georgian President and Clinton ally Eduard Shevardnadze.

“If, in fact, this project is still going forward, we don’t approve and will continue to make clear to Georgian officials that this venture has no connection with or sanction from the U.S. government,” White House spokesman Joe Lockhart said at the time.

Rodham later helped on his sister’s 2008 presidential campaign.

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But she ultimately ended that bid for the Democratic Party nomination and threw her support to eventual President Barack Obama.

Tony did not help Hillary’s failed 2016 presidential campaign, which she lost to President Donald Trump.

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The Associated Press contributed to this article