- April 3, 2026
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Tuesday night Winter Park found out who its next commissioners will be, but it knew long ago who was leaving, as it did in the last round of elections, when Commissioners Karen Diebel and Margie Bridges left after their first terms in office.
And with the soon-to-be departures of Commissioners Phil Anderson and Beth Dillaha, Winter Park is facing a bit of an epidemic: One-term commissioners.
Every single member of Winter Park’s Commission is in their freshman term. That won’t change until at least the next election cycle.
Of course, for many that would represent an ideal scenario. Long-term “career politicians” are traditionally loathed at the national level. For a politician to arrive on the national stage, they’ve frequently been in the game for a while. It’s almost expected that a politician who’s been involved in elected office for so long would prefer to stay that way.
But down at the local level, with the politicians you see shopping at the grocery store, dining in your favorite restaurant along Park Avenue or walking their dog down the street, there’s a personal connection that is never truly lost between the politician and the constituent. They’re a part of the community because they literally live in the city their decisions affect.
For the voters who see decisions made down the street that directly affect their neighborhood, it’s easy to connect the dots between what’s happening in the city and who’s responsible.
It’s also easy to see who’s been responsible with their decision-making. Despite frequent controversies on the dais in the last few years, commissioners in Winter Park have rarely been kicked out for doing a bad job. All the more frequently, they kick themselves out, refusing to run for a second term.
In terms of political longevity, Winter Park’s commissioners are batting well below the local average. It’s easy to see that the wear and tear of politics has done its fair share of disenchanting our commissioners — dog parks, commuter trains and building codes have all turned into firestorms as residents have proven quick to choose sides and spurn their sudden political enemies.
When dealing with a vast political spectrum, it’s tough to say who’s right or wrong and impossible to do it completely objectively.
But the closer you get to the facts of a given political situation — the more you dig, the closer you get to the hard numbers and the daunting red ink — the easier it is to stand behind your decisions.
Bridges found herself frequently in the middle on issues, acting as a peacemaker in an increasingly fractious Commission. She was difficult to predict, because she weighed issues on their own merits. She rarely was accused of having a bias on any issue. As such, she rarely made headlines with controversial stances or angry rants on the dais. She compromised — one of the toughest jobs for a politician.
Though Dillaha aroused contention on the dais for her views on commuter rail and Fleet Peeples Park, she consistently had troves of in-depth research, often from sources across the country, to back up her decisions. Though she made political enemies out of those who disagreed with her, she stood by her convictions, based on an obvious desire to keep financial reins tight in tough economic times for the sake of the city’s future.
For Anderson, who at times found himself frequently voting with the majority and at odds with Dillaha’s decisions, emotion rarely clouded his vote, as he could easily cite figures to back up his decisions.
But those three politicians represented three different legislative approaches. For Anderson, he tended to side with the majority. For Bridges, she tended to split the difference, frequently acting as a crucial swing vote. In a Commission that operates mostly with a majority vote (except on the controversial comprehensive plan supermajority), Dillaha was frequently the lone dissenter, but an important counterbalance for voters whose voice otherwise may not be heard by a unanimous Commission.
All three made the choice to leave the Commission after dealing with controversy in the face of tough decisions they arrived at in their own way. In effect, despite their diligence, they were politicked out of politics.
Half of the candidates in this season’s Commission races ran on a platform that said in one way or another that they would agree with one or more members of the current Commission. Winter Park does need more solidarity, but that should come from individual perspectives arriving at a logical consensus. The last thing it needs is a Commission of “yes men.”