- April 3, 2026
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It has always taken courage to enter Winter Park politics, because to do so is to govern from the floor of a gladiatorial arena. When you walk through those gates onto that dirty floor, surrounded by towering pews of nameless spectators, you’ve become a target to the masses.
Outside that arena floor, armed with buckets of stones, the people are all too ready to start throwing.
When former Commissioner Beth Dillaha, her name hanging in the balance, admitted to sending out a campaign mailer in March that lambasted candidate Sarah Sprinkel as a former lobbyist who was allegedly in the pocket of notorious developers, the stones started flying. Was the mailer excessive? Absolutely. Should its backers have named themselves? Without a doubt.
But why the sudden outrage? That style of campaign advertisement is far from unusual for Winter Park. For years, candidates have had their reputations trashed before they even entered office. Every election cycle, the ads land on doorsteps depicting a close neighbor as a potential Satan incarnate were they to suddenly be in charge of the city.
Were people to educate themselves on the issues based on campaign mailers alone, they would come away thinking that the city had been invaded by an army of darkness hell-bent on destroying the city once their candidate is elected to the five-person City Commission.
Some say skyscrapers would begin shooting up everywhere, transforming Winter Park into a choked metropolis rent to shreds of its former historic charm. To others, an extremist anti-business climate would bankrupt the city and shutter Park Avenue forever. The dust bowl, long since blown away a thousand miles west and most of a century behind us, would come roaring back like a hurricane in Central Park.
Yet despite ludicrous warnings from both sides of the eternal pro/anti-development debate, Winter Park has never realized either of those dystopian extremes.
It defies all campaign mailer logic — seemingly driven by insanity alone, we’ve managed to consistently elect politicians who have been called the end of Winter Park as we know it, just days before voting day. Then we bask in the disappointment of a Winter Park that somehow manages to survive these commissioners’ tenure unscathed but for the horrors of an impending fancy train station and an ordinance to make sure your dog has its shots before it can poop in a public park.
And so now we find ourselves in a slow political season, looking desperately for more compelling outrage to fling like a stone to the head of a fellow resident who dared to step into the spotlight.
When Dillaha said she’d sent out that anti-Sprinkel mailer, Winter Park had its target. And that target had a name. And for many, that was a name they hated for a long time before she finally admitted to mistaking a campaign funding law, intentionally or otherwise.
The anonymous blogs lit up. The stones came in torrents, somehow hitting unrelated former elected officials who made seemingly no enemies while in office. But they had made enemies — just not the kind who were willing to name themselves and stand behind their convictions.
There are plenty of reasons to disapprove of those behind the anti-Sprinkel mailer. It’s politically disgusting and needlessly excessive to the point of a kitschy cliché. But we need to consider the source of that outrage against anonymous mailers, where in the past there was little or none from that same faction.
That’s the problem with this outrage from the shadows: Though there are a few who’ve given a name to this discontent over anonymous mailers — the current Commission and resident Pete Weldon, to name a couple — for many, that outrage has no name.
Anonymity has no place in the type of politics for which the anonymous ironically cheer.