The John Oliver property tax scam: HBO comedian secretly buys Manhattan mansion

So it’s a little surprising to discover that just months before, Oliver had a tax attorney set up two revocable trusts, one for him and one for his wife, to hide the couple’s purchase of a $9.5 million Manhattan penthouse. Then he used a tax loophole created by Donald Trump himself back in the 1970s, when the current president was merely a prominent New York real estate developer and aspiring celebrity author.

The loophole in question is the banally named “421-a” tax dodge, which was recently attacked in a Daily News op-ed written by two New York state Democrats, one a senator and the other an assemblyman. They said that the original 421-a tax exemption was “designed to encourage new development in locations that were vacant or underutilized,” but that Trump wanted to use it in 1980 when he bought Bonwit Teller in midtown Manhattan. The plan was to tear it down and build Trump Tower, which would mix office space and luxury condos.

“Told by Mayor Ed Koch that the Bonwit site could not qualify for a 421-a tax break, Trump and his lawyer — the infamous Roy Cohn — sued the city,” the News op-ed recalls. “In the end, they won a tax exemption worth $50 million for the extravagant Trump Tower. More importantly, Trump’s lawsuit established that all new development, even luxury projects, would be automatically eligible for the 421-a exemption.”