The Recombobulation Area is a 19-time 21-TIME! Milwaukee Press Club award-winning opinion column and online publication founded by Milwaukee journalist Dan Shafer.
Scot Ross did political communications and research at the state and federal levels for 25 years. His last dozen years in politics, he ran One Wisconsin Now, an opposition research and communication outfit, and for the last 15 years, he’s been the liberal pundit for PBS Wisconsin.
He has some thoughts on the upcoming election.
We talked about Tom Tiffany not paying any income taxes for years, something Ross and One Wisconsin Now researched years ago during Tiffany’s time in the state legislature, that for some reason, isn’t getting all that much attention now.
We also talked about the “Dodgers of politics” — the billionaire Uihleins and Diane Hendricks, who have been funding Tom Tiffany to an exorbitant degree.
Ross also discussed campaign strategy and why now is the time for Democrats to go negative, as spending from outside groups is overwhelmingly favoring Tiffany and only a small percentage of Crowley’s ads are negative ones, per the Milwaukee Journal Sentinel, and whether Democrats are “leaving cheddar on the table.”
“If the race is focused on the fact that Tom Tiffany and Donald Trump are together 100% of the time, Tom Tiffany loses 100% of the time.” said Ross.
For a beat-by-beat breakdown of this episode, see these topics and timestamps below.
00:00 Intro: Brewers lead the Dodgers, 22 days to the midterms
00:45 Introducing Scot Ross (One Wisconsin Now, PBS Wisconsin)
01:45 Baseball detour: Pirates futility and the Brewers
02:49 The One Wisconsin Now banner plane at Miller Park
03:38 Uihlein, Hendricks, and the “Dodgers of politics”
04:04 Journal Sentinel: outside spending favors Tiffany
05:09 Unprecedented spending concentration: 90% from three donors
06:44 The 2015 coordination loophole Tiffany voted for
08:21 Why outside groups pay more for ads, and the Uline-Tiffany relationship
09:24 Billionaire ROI: tax cuts and Tiffany’s “no tax hikes” pledge
11:48 Eliminating the state income tax
12:55 Why states without income taxes can afford it, and why Wisconsin can’t
13:50 Democratic outside spending: only $1M of $11M on negative ads
15:00 Democrats’ statewide record when they outspend Republicans
16:25 “I’m terrified”: the Democratic complacency problem
17:29 Making the race about Trump and Tiffany, not Crowley
18:27 Tiffany’s unpaid taxes story and why it’s not being used
21:32 Attack, never defend: Tiffany’s toxic record
22:12 Can a sitting congressman win the governor’s race?
23:54 Trump’s low approval, gas prices, and the voter-motivation question
25:26 “Anger wanes”: why Democrats must keep reminding voters
25:51 Why Crowley needs a Democratic legislature (Robin Voss and the budget)
26:20 Congressional races: Rebecca Cook, Mitchell Berman, and the DCCC
27:15 “Leaving cheddar on the table”: calling for 100% negative
29:05 Keep the message simple: a hammer, not a carving knife
29:55 Need for negative ads on Tiffany, and the Walker-era record
31:08 What a Democratic trifecta could accomplish
31:35 The “Slap Shot” analogy for the final three weeks
32:19 Lessons from 2008: it’s in our hands
32:52 Scott Ross’s play, The Senator Can See You Now
35:01 The play’s non-partisan, profanity-free approach
36:04 Final thoughts: “Go fight, win”
36:33 Outro
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Dan Shafer is an independent journalist from Milwaukee who writes and publishes The Recombobulation Area. He worked with Civic Media from 2024 to 2026. He’s written for The New York Times, The Daily Beast, Heartland Signal, Belt Magazine, WisPolitics, and Milwaukee Record. He previously worked at Seattle Magazine, Seattle Business Magazine, the Milwaukee Business Journal, Milwaukee Magazine, and BizTimes Milwaukee. He’s won 24 Milwaukee Press Club Excellence in Journalism Awards. He’s on Twitter at @DanRShafer.
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