Osceola County Democrats Chair Kathy Winter, 60, and her son Jason, 28. Photo: Lars Gesing/CU News Corps
SIOUX CITY, Iowa – For the longest time, Kathy Winter never put up campaign yard signs on her front lawn. She just didn’t want to hurt her husband’s business.
She firmly believes a lot of people would have stopped coming into the family’s liquor store in Sibley, 10 miles south of the Minnesota border and far up in Iowa’s rock-solid conservative northwest, if they had known the hands that fed them their booze belonged to a liberal.
For every one Democrat, there are five Republicans in Osceola County. But when her son Jason, himself a Democratic activist with a political science degree from the University of South Dakota, had dragged her to a John Kerry campaign event in neighboring Sheldon in 2004, Kathy caught the bug to go on, Quixote-like, and fight the odds.
Ever since, progress has been slow – painfully slow. “Not a snowball’s chance in hell that a Democratic candidate is going to win this county,” she still readily admits, more than a decade later, by now filling the shoes of the Osceola County Democrats chairwoman.
Earlier this month, when progressive presidential hopeful Bernie Sanders visited Sibley — a town of 2,800 — about 200 people showed up to the event. Winter and the Osceola Democrats had planned for half of that.
Sanders’ visit was a good day for Kathy. But she says there are many more “when you are just frustrated a lot.”
Like when Jason, then an intern on the Hillary Clinton Iowa campaign, had written a letter to the editor of the local newspaper during the 2008 cycle touting his boss’s achievements on education, and the Winters’ then found an anonymous note in their mailbox that called them baby-killer supporters.
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Or when Kathy – a medical technologist with a now-retired husband at home – finally did put up a yard sign in 2012 to support Christie Vilsack’s run against staunchly conservative U.S. Rep. Steve King. The I-can’t-believe-you-would-do-this looks followed the family around town.
“It’s a rough road up there,” Kathy says and doesn’t hold back on why she thinks that is. “It’s not that our neighbors and co-workers are bad people. They just have a total disconnect between the very Christian way they are supposed to live their life and what that translates to when they vote.”
To help turn the tide, Kathy found an ally in Kim Weaver, another frontline northwest Iowa progressive activist who then spearheaded the next-door O’Brien County Democrats and who just announced her bid to challenge U.S. Rep. Steve King in the state’s 4th Congressional District. When every county chair received an email touting a grant program put together by the office of now-retired Democratic U.S. Sen. Tom Harkin in 2013, Weaver called her friend in Osceola.
“She said: ‘How about if we both apply?’ Kathy remembers. “’We write our grant individually, but we both have the same goal which is to form a loose collaboration to work together in this very red area.’”
Both chairs got funding. They invited two other neighboring counties, Sioux and Lyon, to join their ranks – the SOLO Democrats were born, named after the initials of their four members.
But even with quadrupled forces, getting people to attend the Democratic caucuses in the four-corner coalition is an uphill battle.
“The caucus is different than any other process,” Jason says. ”You have to get up in front of everyone and say, ‘I am a Democrat and this is the candidate I am supporting.’ In northwest Iowa, that is something that can be very intimidating.”
The two still chuckle when they remember Hillary Clinton’s ’08 mantra, “Caucusing is Easy”
“No, no,” Kathy stews. “A primary is easy. You have a polling place open for eight to 10 hours, maybe even 12. You don’t come home from work on a cold January or February night in northwest Iowa. And then you have to think about getting your coat and boots back on to go out and stand up in front of your neighbors to say who you are for. There is nothing about that that’s easy.”
But then again, nothing in the Winters’ political life has ever exactly been easy anyway.