The Mocking-Jay in the coal mine

Jay Leno is indeed an oddity. He is a leftist who learned late in life that leftism isn't the Utopia he was sold. Jay is one of a handful of leftists who never properly hated the USA.
Leftism is a religion that requires you make a deal with the Devil. Jay sold his soul for money and fame. And now at the end of his life, the thing that brings him maximum joy (his cars & motorcycles), well, Satan came to collect on the deal. And it turns out the love of Jay's life is the collateral to be forfeited to his master.