Tiffany's Willow Inc., owed and paid no state income taxes for more than a decade through 2016 - then paid just $65 in in 2017, $308 in 2018 and $240 in 2019, the records show. And his Wisconsin River Cruises Inc., owed and paid no state income taxes between 2007 and 2013, according to the records.Well how could that be?
Rachel Detert, an accounting professor at Marquette University, said it's possible that Tiffany didn't have a net tax liability some years because of losses "passed through" Wisconsin River Cruises Inc. since it was an S corp…. "A tax loss does not necessarily mean that the business was economically unsuccessful," said Detert, who is also a certified public accountant. "Taxable income is calculated under tax rules and can differ from financial statement income and cash flow." She added the depreciation allows a business to recover the tax cost of qualifying property, and that losses can carried forward and used against Wisconsin income in as many as the next 15 tax years.I also agree that this isn’t really indicative of lawbreaking or Tiffany being a lousy business owner (although he definitely has the “mediocre local yokel who doesn’t know a thing about how corporations in big towns work” vibe). But S corps? Pass-throughs? This sounds familiar….Oh yeah, I remember now!
From ProPublica, in August 2021, and how Ron Johnson shaped Trump/GOP Tax Scam 1.0 in 2017.GOP megadonors Diane Hendricks and Dick and Liz Uihlein were able to claim a combined $215 million in deductions in 2018 because of provisions @SenRonJohnson put into the tax cut Trump signed, according to @propublica. https://t.co/mniK4o6R0I
— Patrick Marley (@patrickdmarley) August 11, 2021
Johnson’s demand was simple: In exchange for his vote, the bill must sweeten the tax break for a class of companies that are known as pass-throughs, since profits pass through to their owners. Johnson praised such companies as “engines of innovation.” Behind the scenes, the senator pressed top Treasury Department officials on the issue, emails and the officials’ calendars show. Within two weeks, Johnson’s ultimatum produced results. Trump personally called the senator to beg for his support, and the bill’s authors fattened the tax cut for these businesses. Johnson flipped to a “yes” and claimed credit for the change. The bill passed.And guess who got the biggest tax cut for these “small, family-owned” businesses?
Dick and Liz Uihlein of packaging giant Uline, along with roofing magnate Diane Hendricks, together had contributed around $20 million to groups backing Johnson’s 2016 reelection campaign. The expanded tax break Johnson muscled through netted them $215 million in deductions in 2018 alone, drastically reducing the income they owed taxes on. At that rate, the cut could deliver more than half a billion in tax savings for Hendricks and the Uihleins over its eight-year life. But the tax break did more than just give a lucrative, and legal, perk to Johnson’s donors. In the first year after Trump signed the legislation, just 82 ultrawealthy households collectively walked away with more than $1 billion in total savings, an analysis of confidential tax records shows. Republican and Democratic tycoons alike saw their tax bills chopped by tens of millions, among them: media magnate and former Democratic presidential candidate Michael Bloomberg; the Bechtel family, owners of the engineering firm that bears their name; and the heirs of the late Houston pipeline billionaire Dan Duncan.Move ahead to 2026, and guess who are by far the biggest donors to Tom Tiffany’s campaign (via the Wisconsin Republican Party)? Yep, Diane Hendricks and the Uihleins, happily kicking back their gains from these tax cuts.
Tiffany, who is the presumptive Republican nominee for governor, reported raising $8.7 million during the [Jan 1 to June 30, 2026] period, bringing his total raised over the course of his campaign to more than $10 million…. Over $6.1 million of Tiffany’s contributions came from transfers from the Republican Party of Wisconsin. The state party received more than $6 million in contributions from megadonors including $4 million from Richard and Elizabeth Uihlein, owners of Uline shipping supply company located in Pleasant Prairie, Wisconsin, as well as $2.5 million from Diane Hendricks, ABC Supply CEO and a billionaire from Beloit….Total coincidence! That S corp tax cut not only continued in Trump/GOP Tax Scam 2.0 (which Tom Tiffany voted for in Congress), but also gave extra tax cuts to people like Hendricks and the Uihleins due to a work-around to the limits on the State and Local Tax (SALT) deduction.
For business owners of pass-through entities (partnerships and S corporations), the PTET [for pass-through entities] survives under OBBBA! Contrary to some expectations, the new law did not eliminate this strategy for payment of state income taxes. In many states, business owners in pass-throughs can elect for the entity to pay state and local income tax at the entity level. These taxes are deductible by the entity for federal tax purposes and reduce the flow-through income taxed to the business owner personally. This treatment allows the effective deduction of state and local taxes without being subject to the federal SALT limitations, saving the owner significant federal tax. For example, a Kansas S corporation manufacturing company with $2 million of pre-tax income elects to pay the Kansas PTET at 5.7 percent, resulting in $114,000 (0.057 × $2 million) in Kansas tax at the entity level. The business owner is then taxed federally on only $1,886,000 ($2,000,000 − $114,000), not $2 million. The $114,000 is not counted as state and local tax on the individual’s income tax return. It is deducted by the business, reducing taxable income for the owner who, in this example, is at the top marginal federal rate of 37 percent, resulting in $42,180 (0.37 × $114,000) federal savings on this amount. Additionally, the business owner may still deduct up to $10,000 of other state and local taxes, such as real estate tax, personal property tax, or state income tax on other income if itemizing deductions.Cool deal, eh? The business owners basically keep two sets of books – one for their company and another for themselves, and get to lower taxes on both of them depending on how they describe where they get the money from. Given that Tom Tiffany listed his net worth as less than $300,000 in 2024, it adds up that he personally may not have had much to pay for state taxes for much of the 2000s. I don’t think he did anything illegal and it’s conceivable that his businesses may not have made much money at all on their own in those years. That’s not unusual for something of the size of Willow Inc. or Wisconsin River Cruises in the Northwoods. But it also demands questions as to how much he might have benefitted from write-offs at the federal level from Trump/GOP Tax Scam 1.0 and 2.0. And we certainly should ask why Tiffany’s and WisGOP’s largest donors got some of the biggest tax breaks from those Scams, and what is being promised in kickbacks to Hendricks and the Uihleins and other Wisconsin oligarchs should this state be foolish enough to elect Tiffany as Governor.



















