Rick Jackson, the billionaire Republican candidate for Georgia governor, faces a Tuesday runoff while battling the IRS over $90 million in tax deductions claimed from four money-losing independent films. His company, Jackson Investment Group, donated movie rights to charities he controls, then sought massive deductions that the IRS has challenged in court.

The largest dispute involves 2019's "The Best of Enemies" starring Taraji P. Henson and Sam Rockwell. Despite earning only $10 million at the box office against a $40 million valuation, Jackson's company claimed the full deduction. The IRS rejected this and other claims totaling $32.85 million for "Queen Bees" and $18 million for religious films.

Jackson previously prevailed in a 2023 trial where a federal judge reduced but largely upheld his company's position on an $18 million deduction case. However, the ongoing litigation raises questions about business judgment as his films struggled to find distributors and performed poorly commercially. His campaign argues he won't be "bullied" by federal agencies.

The tax disputes could undermine Jackson's credibility on fiscal responsibility as he campaigns on making Georgia more affordable. While he's positioned himself as a MAGA-aligned candidate with Trump endorsements, these cases highlight potential vulnerabilities about wealth accumulation strategies that may not resonate with voters concerned about tax fairness.