Andrew Filipowski asked the IRS to settle a roughly $140 million tax debt for $1.5 million. The debt followed his use of losses from a partnership the Tax Court had found to be a sham tax shelter; he also filed several later tax returns only after IRS prompting. The IRS rejected the offer in compromise on public-policy grounds, and the Tax Court granted summary judgment to the Commissioner. The Eleventh Circuit held that the undisputed debt-to-offer disparity and filing history supported the IRS’s concern that accepting the offer would weaken voluntary tax compliance. It affirmed; disputes about collection and other facts did not change that conclusion.