John Paul Reddam has a varied resume: businessman, former college philosophy professor, owner of the 2012 Triple Crown contender I’ll Have Another—and failed tax shelter investor.

The U.S. Court of Appeals for the Ninth Circuit on Friday ruled that Reddam couldn’t claim a $50 million loss generated by a now discredited KPMG tax shelter. Reddam had attempted to use the sham loss to offset a $48 million gain from the sale of his mortgage finance company, DiTech Funding Corp., to GMAC Mortgage Corporation in 1999. The Ninth Circuit agreed with the U.S. Tax Court that the shelter, called the Offshore Portfolio Investment Strategy (OPIS), lacked economic substance.