Snowbird Jeter May Owe New York Millions

Often, dual-residence taxpayers are unable to account for their whereabouts on every single day of the year, said Hegt, who has represented several clients who were just unable to prove they were in one state of another, ultimately losing cases against the state.

"I don't know that they're being too tough on him, only because that's usually how the state operates," said Hegt. "And New York must know something because there are all sorts of hazards of this kind of litigation."

"If they lose this case and a court case is on file with Jeter's facts and circumstances of having a home in New York and one in Florida and a business presence in New York, it's going to be horrible from the New York perspective," said Hegt. "It will open all kinds of doors for the ordinary business man, and I would imagine they've considered that and are not looking to publicly lose a court case that could have ramifications well beyond Derek Jeter not paying his taxes."