¶ Overview
Tiffany campaigned to fight high taxes as a “successful small business owner,” but Wisconsin Department of Revenue records told a different story. He went five straight years, from 2006 through 2010, without paying personal state income taxes and paid none again in 2019.
His businesses also went years without paying state income taxes. Tiffany’s Willow Inc. paid none for more than a decade through 2016 and Wisconsin River Cruises Inc. paid none from 2007 through 2013. Tiffany blamed years of paying no state income taxes on the financial crisis, recession, business costs, and depreciation.
Political analyst Scot Ross argued the record raised questions about Tiffany’s business pitch, saying, “The dam man didn’t pay his damn taxes.”
¶ Tiffany Bragged About His Small Business “Success” Despite Years Of Paying No Personal Or Business State Income Taxes
¶ Tiffany Touted His Small Business Success Despite More Than A Decade Without Paying Business State Income Taxes And Five Straight Years Without Paying Personal State Income Taxes
August 2026: Milwaukee Journal Sentinel: Wisconsin Department Of Revenue Records Showed Tiffany Paid No Personal State Income Taxes From 2006 To 2010 And His Businesses Went Years Without Paying State Income Taxes Despite Touting His Small Business “Success.” According to the Milwaukee Journal Sentinel, "U.S. Rep. Tom Tiffany is campaigning for Wisconsin governor as a successful small-business owner. 'Tom and his wife Chris owned and operated Wilderness Cruises in Wisconsin’s beautiful Northwoods for 20 years, and he served as the dam tender on the Willow Flowage for 29 years,' his campaign website reads. 'Yes, he was a dam man!' But Tiffany and his business went years without paying state income taxes, Department of Revenue records show. Tiffany had zero net state liability - meaning he owed and paid no personal state income taxes - for the years 2006 through 2010, as well as 2019, the records show. 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." [Milwaukee Journal Sentinel, 8/26/26]
- August 2026: Milwaukee Journal Sentinel: Tiffany Paid No Personal State Income Taxes From 2006 To 2010 And Again In 2019, Before His Tax Payments Increased After He Was Elected To Congress. According to the Milwaukee Journal Sentinel, “Tiffany paid just $681 in personal state income taxes in 2005, then paid no income taxes between 2006 and 2010, according to state Department of Revenue records. In 2011, the year he took office in the state Assembly, he paid $2,212 in personal state income taxes, and between 2012 and 2018, he paid between $1,680 and $2,445. Tiffany paid no state income taxes again in 2019, then has paid between $4,613 and $8,432 in net taxes per year since 2020, when he was first elected to Congress. Members of Congress typically make $174,000 per year." [Milwaukee Journal Sentinel, 8/26/26]
¶ Tiffany Promoted Himself As A “Successful Small Business Owner” And Promised To Fight High Taxes Yet Cited The Financial Crisis, Business Costs, And Depreciation To Explain Years Without Paying State Income Taxes
Tiffany Claimed He Was A “Successful Small Business Owner” Who Owned And Operated Wilderness Cruises With His Wife For Two Decades. According to Tiffany’s website, "Tom Tiffany is a lifelong Wisconsinite. He grew up on a dairy farm in western Wisconsin, milking cows and feeding calves at sunrise. He attended public school, worked his way through UW-River Falls, and went on to be a successful small business owner. Together with his wife Chris, Tom owned and operated Wilderness Cruises in Wisconsin’s stunning Northwoods for two decades."
[Tom Tiffany For Governor, Archived 8/28/26]
June 2026: Tiffany Claimed He Ran For Governor After 20 Years As A Small Business Owner To Fight High Taxes. According to Tiffany’s Twitter, "Great to visit Peters’ Boyz Texas BBQ and il Bar Coffeehouse & Bistro, a veteran-owned business, in Kimberly. After 20 years as a small business owner, I ran for office to fight red tape and high taxes. Let’s get government out of your way and unlock Wisconsin’s potential."
[Twitter, @TomTiffanyWI, 6/19/26]
August 2026: Milwaukee Journal Sentinel: Tiffany Defended Years Of Paying No State Income Taxes, Citing The Financial Crisis, The Recession, And Costs Of Running His Seasonal Business. According to the Milwaukee Journal Sentinel, "Tiffany, 68, told the Milwaukee Journal Sentinel that Wilderness Cruises, his northern Wisconsin seasonal dinner boat and excursion business, faced some tough times over the years. 'As any small business owner will tell you, it isn’t always easy,' Tiffany said in a statement. 'During the times surrounding the financial crisis and recession, times were tough for all businesses, especially seasonal businesses like ours that relied on tourism. He said the business employed both full-time seasonal and part-time workers, averaging about 15 employees per year. 'Before we ever took home a dollar, we had employees counting on us, fuel to buy, repairs and improvements to upgrade the boat and equipment, and countless other expenses that come with running a business,' Tiffany said. 'We also paid thousands in property taxes and other business obligations, including personal property taxes, unemployment insurance, and payroll taxes, such as Social Security and Medicare." [Milwaukee Journal Sentinel, 8/26/26]
August 2026: Milwaukee Journal Sentinel: Tiffany Said He Had No State Income Tax Liability In 2019 Because Of Depreciation. According to the Milwaukee Journal Sentinel, "He added that he had no state income tax liability in 2019 due to depreciation on the boat and other business equipment. 'Through it all, I loved running our small business with Chris, creating jobs in our community, and serving families from every corner of Wisconsin,' Tiffany said. 'We know what it’s like to sit down at the kitchen table, look at the numbers, and figure out how to make it work when costs go up." [Milwaukee Journal Sentinel, 8/26/26]
¶ Analyst Scot Ross Said “The Dam Man Didn’t Pay His Damn Taxes” And Questioned Tiffany’s Record As A Successful Business Owner
August 2026: Milwaukee Journal Sentinel: Democratic Analyst Scot Ross Said “The Dam Man Didn’t Pay His Damn Taxes” And Accused Tiffany Of Either Scheming To Avoid Taxes Or Lying About Being A Successful Business Owner. According to the Milwaukee Journal Sentinel, "Scot Ross, a Democratic analyst, criticized Tiffany for campaigning as a successful businessman. 'The dam man didn't pay his damn taxes,' he said, referring to Tiffany's TV ad slogan, 'Time to send in the dam man. When Ross was executive director of the Madison-based One Wisconsin Now, the liberal group found Tiffany's Willow Inc. had no tax obligations dating back to 2001. 'Either Tiffany schemed to avoid paying his taxes or he was lying when he said he was a successful business owner,' Ross said." [Milwaukee Journal Sentinel, 8/26/26]