SPRINGFIELD, IL — Gerald Whitmore, 68, a buttoned-up libertarian fixture who has been running for public office every other year since 1974, was once again stunned Tuesday night after losing his 27th consecutive election, this time for county treasurer — a position he described as “critical to restoring constitutional order at the local level.”
Whitmore, who spent the entirety of his campaign delivering hour-long lectures at regional Libertarian Party meetings on the original intent of David Nolan, was reportedly shocked to discover that once again, no one outside of the LP bubble had any idea he was even running.
“I really thought this was the year,” said Whitmore, still wearing his campaign pin featuring a faded porcupine and the slogan “Smaller Government, Serious Tie.” “The room at the Central Illinois affiliate nodded in agreement when I said the 10th Amendment is our last line of defense. That means something.”
Asked if he had engaged with non-libertarian voters, Whitmore appeared confused. “Well, I sent out a newsletter to our email list. We’re up to 86 people — not including bounces.”
Sources confirm Whitmore has lost races for city council, state house, clerk of courts, and once, memorably, park district board in a special election that he blamed on “that anarchist faction hijacking the county convention with their weed talk.”
He insists the losses are never about his message or his delivery, but always due to external sabotage — most recently a younger, more energetic candidate in the LP who wore jeans to a candidate forum and once tweeted something “rude about zoning enforcement.”
“You can’t build credibility when you’ve got people talking about abolishing gun laws and calling public schools indoctrination camps,” Whitmore said, visibly agitated. “That kind of radicalism makes us look unserious — unlike me, who campaigned on indexing property taxes to voluntary arbitration courts.”
When asked if he plans to run again, Whitmore scoffed. “Of course. This is about principle, not popularity. One of these days, voters will appreciate someone who brings self-printed trifold brochures and references the 1972 platform.”
At press time, Whitmore was seen typing up a resolution condemning “online tone” from the state party’s official X account.
