“It’s very clear that the eyes of the world are going to be on Wisconsin for the next 18 months, and we intend to draw some conclusions about who is going to win,” Scot Ross announced in the kickoff episode of his new podcast with co-host Bill McCoshen, Win2020 with McCoshen and Ross.
Ross, a Democrat, and McCoshen, a Republican, have accumulated many years of political experience advising many candidates between them. And they clearly enjoy the game—and each other. Trading war stories, ribbing each other about past losses and comparing notes as they analyze politics, they shed a lot of light on our fickle, fractious and critical swing state. That’s good news for anyone interested in sorting out what it takes to win Wisconsin, a topic that is of intense national interest.

As McCoshen, Ross, and their first guest–Sen. Tammy Baldwin–all agreed: Wisconsin is ground zero for the 2020 presidential election.
Candidates in the crowded 2020 presidential field would do well to listen to Tammy, who won her 2018 re-election bid by 11 points and knows a thing or two about how to connect with voters here–as Ross observed. Take an unnamed Democratic presidential candidate who arrived for a swing through the state and, as Sen. Baldwin told it, immediately made clear that he knew nothing about the dairy crisis.

Baldwin filled him in, and he did better at his next stop, she told her appreciative podcast hosts.
It’s this sort of storytelling and banter that could help out-of-state politicians avoid painful gaffes (Remember John Kerry’s reference at a Madison rally to “Lambert Field”?) and maybe even get beyond stereotypes to truly understand the aspirations of Midwestern voters.
Baldwin was a good choice as a first guest, not just because she won so handily in 2018, but because she has deep credibility, including in districts where Donald Trump won in 2016. Baldwin won in 17 counties that went for Trump, McCoshen pointed out. He asked her if anyone in the current field of Democratic presidential contenders could achieve that.
Yes, Baldwin said, although she also made clear that she will not endorse anyone. She wants to offer her counsel to all the candidates, as someone who knows how to win in this battleground state. When Ross asked her about talk that Baldwin would make a good running mate, she said nothing to dispel the idea, only noting that it shows she’s done a good job of spreading the word that the road to the White House goes through Wisconsin.
The key to Wisconsin, Baldwin told McCoshen and Ross, is not getting too caught up in partisanship, and understanding “Wisconsin values and economics.”
“People across Wisconsin want solutions to their challenges and are not all that interested in Republican versus Democrat,” she said. “They’re interested in who you’ll stand up to, and who you’ll stand up for.”
She distinguished between partisan fights and fights against powerful interests, including the pharmaceutical industry, where voters of different political parties are looking for a champion.
She has connected with Wisconsinites by being an outspoken progressive (as well as the first woman and first openly gay senator from Wisconsin), who is proud to take up the mantle of the great progressive Sen. Bob La Follette, but who also has a granular, no-nonsense understanding of how Wisconsin works.
Like other states across the Upper Midwest, Baldwin said, “We are a state that makes things.”
You have to know something about manufacturing and the trades to connect with voters here, she said. Wisconsin is a hard-working state, but lately people are not seeing their hard work rewarded in their earnings. Baldwin has addressed that and connected with Wisconsinites with her Buy American initiatives. It’s been a winning political position, and one also adopted by Donald Trump.
But Trump’s trade wars and tariffs have hurt Wisconsin industry, Baldwin noted—especially dairy.
“Eau Claire is where they calculate what that price of milk should be,” she added. That radiates out across the country. You can’t go up there and not understand we are in a dairy crisis.”. (Pity that poor out-of-state candidate who did not understand it. You get the feeling he went home with a binder on milk prices from Baldwin.)
However politically divided Wisconsin has been since the Scott Walker era, nothing brings people together like home-state pride. Ross, McCoshen and Baldwin basked in it on the podcast, looking ahead to the 2020 Democratic National Convention in Milwaukee.
McCoshen cut his teeth working for three-term governor Tommy Thompson, the longest-serving governor in Wisconsin history, a major Badger State booster and the king of Wisconsin politics. Well, at least he was until Baldwin beat him in her first Senate race and Walker won the governorship and helped push the GOP in a new direction, sowing division and bitterness.
McCoshen also worked for the recently defeated Walker. But his hero is the friendlier, more bipartisan Tommy, whose political philosophy was a lot like Tammy’s. In his gubernatorial races, Thompson appealed to voters across party lines, with his deep understanding and connection to all things Wisconsin.
McCoshen described how, at the age of 23, he started working for Tommy. He recalled how Thompson won over his parents, Democrats from Superior, as he rode to victory capturing blue-county voters not just in up North but also in Dane and Milwaukee Counties.
Ross’s political heroes are two pathbreaking women in Wisconsin politics, former Democratic attorneys general Kathleen Falk and Peg Lautenschlager, who once fought a bitter primary battle.
Only his deceased mother ever knew who he voted for in that primary, Ross said.
The bitterest campaigns are often primary battles, Ross and McCoshen agreed.
When candidates realize there’s “not a lot of time left on the clock, it gets real nasty real quick,” McCoshen observed. He predicted the knives will be out in earnest as the Democratic presidential primary goes on.

But the podcast hosts and their guest Tammy Baldwin are, for now, staying happily above the fray.
“I want to offer my insights in running a great campaign back in 2018 and help these candidates understand the Wisconsin values they need to reflect,” said Baldwin. “ I think if I endorsed there would be less likelihood of getting the opportunity to share that insight with all of them.”
McCoshen and Ross will be offering plenty of insights, too—tune in to Win 2020 with McCoshen and Ross to check them out.
Our stories may be republished online or in print under Creative Commons license CC BY-NC-ND 4.0. We ask that you edit only for style or to shorten, provide proper attribution and link to our web site. Please see our republishing guidelines for use of photos and graphics.