In the closely watched, and highly symbolic, District 21 race, labor attorney Andrew Schauer crushed 10-term incumbent David Wiganowsky, ending the supervisor's 20-year run representing a once reliably conservative swath of the county.
Of the district's eight precincts, Wiganowsky, 54, eked out a victory in just one: the town of Burke, by 27 votes.
"I'm on cloud nine," Schauer said by phone as his supporters and other politicos gathered Tuesday night at the Italian Workmen's Club on Regent Street to celebrate the progressive victory. "It's an amazing feeling. I'm full of gratitude for my family, friends and other officials who supported a first-time candidate."
Across town, Wiganowsky tended bar at Wiggie's, the Aberg Avenue tavern he owns, while the results came in. He didn't know the outcome when approached by a reporter for comment.
"Did I lose?" he asked.
Assured that he had in fact lost, Wiganowsky managed to find a little solace in the fact that his political star seemed to have extinguished.
"He did crush me," Wiganowsky said, "but I'm proud he had to spend all of that money to do it. He had to spend a lot of money to defeat me."
(According to financial disclosure reports filed by the candidates last week, Schauer spent $8,248 of the $12,150 he raised during the campaign, nearly double the $4,455 Wiganowsky reported spending from his $11,800 war chest.)
In the six remaining competitive races, progressives won by large margins in all but one.
UW-Madison student Leland Pan, 21, won a second term, taking 55% of the District 5 vote.
Maureen McCarville handily defeated Dustin Wichmann, 23, with 57% of District 22 voters sending her back for a third term.
One-term incumbent Dorothy Krause, 57, took 58% of the District 27 vote. Both Krause and her opponent, 33-year-old Patrick Stern, are Fitchburg City Council members.
Abigail Wuest, a 34-year-old assistant attorney general with the state's justice department, outdid opponent Todd Osborne, 45, netting 57% of the District 28 vote.
Voters in District 30 gave political upstart Jerry Oâ€™Brien, 49, his second loss to four-term incumbent Patrick Downing, 64, who won handily by securing 67% of votes.
If there was a glimmer of sunshine for Dane County conservatives, it likely came from Mike Willett's victory over retired school teacher Pat McPartland, 62, in the District 32 race.
Willett, 55, lost the seat in 2012 to Erika Hotchkiss, who is stepping down after one term.
Wiganowsky blamed newly drawn political districts for his loss. His reconfigured district, drawn up by the county board, now includes a large slice of northeastern Madison, a solidly Democratic enclave.
"Once those lines were redrawn I knew it was going to be tough," he said.
Democrats waiting for Schauer's arrival at the Italian Workmen's Club seemed to relish this victory more than others, particularly because Wiganowsky for 20 years seemed invincible.
"It is huge," said Mike Basford, chair of the Democratic Party of Dane County. "We've ran candidates against him before, but he was one of those incumbents that was difficult to run against. But he had been in office too long and was out-of-touch with his constituents."
Board chair John Hendricks chalked it up to voters' evolving views on county government.
"He's one of those people who doesn't see a need for county government," Hendricks said.
As for what his next move might be, Wiganowsky said he hadn't given it much thought beyond "feeling bad for awhile."
"I knew I couldn't win Madison," he said. "But life goes on. I served for 20 years; I had a good run."
Voters Tuesday night also approved two advisory referendums, one calling on state lawmakers to legalize marijuana for adult recreational use (64%), the other asking for a non partisan group to oversee political redistricting rather than leaving it to the party in control of the Legislature (82%).
[Editor's note: This article is corrected to note that the Dane County Board is responsible for its own redistricting.]