Casino titan Sheldon Adelson has given half a million dollars to help keep Donald Trump’s cronies out of federal prison.

On Friday, ABC News reported that Las Vegas Sands boss Adelson and his wife Miriam had contributed $500k to the Patriot Legal Expense Fund Trust, which was set up in February 2018 to help Trump associates caught up in special counsel Robert Mueller’s probe into Russian interference in the 2016 presidential election.

The Adelsons’ $500k gift is reportedly the Trust’s largest contribution to date and more than three times the next highest donation. Phil Ruffin, another casino industry veteran who once planned a Las Vegas joint venture with Trump, reportedly gave the fund $50k.

The Adelsons have been major Republican campaign donors for years and were early supporters of Trump’s presidential aspirations. Following the 2016 election, Adelson gave $5m to Trump’s inaugural committee and Trump awarded Miriam the Presidential Medal of Freedom last November.