Winter Garden City Commissioner Robert “Bobby” Olszewksi’s filing for Scott Boyd’s seat on the commission has been coming for months.
By Jacob Engels
For the better part of six-months, political circles have been buzzing about a probable Olszewski campaign to fill the seat of termed out Orange County Commissioner Scott Boyd in District 1.
Back in January, Betsy VanderLey, a political consultant and member of the Planning & Zoning Board for Orange County, was the first credible candidate to formally file paperwork and start campaigning. VanderLey, a longtime ally of Boyd, has benefited from that proximity and netted an impressive first month of fundraising.
However, after revelations of a potential violation of county law, VanderLey faced a slew of negative press and was the subject of an ethics complaint. The complaint alleged that Vanderlay violated Sunshine Laws, by communicating with powerful land developers about matters that were appearing before the Planning & Zoning board.
Following a nearly $35,000.00 fundraising haul in the first month, her contributions plummeted to under $5,000.00 for the second month. Structural support from Boyd and other West Orange donors and power-brokers seemed to fizzle.
Now, with VanderLey’s campaign in political purgatory, Winter Garden Commissioner Bobby “O”, saw his opening. Olszewski, who was never supposed to win his campaign to become a commissioner in Winter Garden.
Dr. Olszewski is an aggressive campaigner and high-energy retail politicker.
“Orange County District 1 deserves genuine leadership as together we place the ‘Residents and Community First’ in Bay Lake, Dr. Phillips, Gotha, Horizon West, Hunter’s Creek, Lake Buena Vista, MetroWest, Oakland, Ocoee, Orlando, Tildenville, Williamsburg, Windermere, and Winter Garden,” said Olszewski.
“In Orange County growth is inevitable, but how you manage that growth is critical. Look at all of the great things we have accomplished in Winter Garden with smart growth by putting our ‘Residents and Community First’ in the decisions that we made.”
Olszewski’s bid for Orange County Commission will be defined by his ability to catch up to VanderLey in the fundraising department, and how well he packages himself to voters. What makes him a better choice than VanderLey or other candidates that could emerge? Will he run an equally aggressive campaign this time around?
“We can continue to grow our communities with direct input from our residents to ensure that our quality of life is not compromised by special and personal business interests,” Olsewski texted us shortly after filing.
Sources tell the East Orlando Post that Dr. Olszewski, who once considered a state house bid to replace Representative Steve Precourt, has incredibly high name ID and favorables in West Orange County.
“His name ID relative to his short time as an elected official still in his first term was shocking. He could have easily edged out Eric Eisanagule, but decided to finish out his term and fulfill his obligations to the residents of Winter Garden. If he his able to keep up with Betsy financially, he wins. She has no name ID and would have to spend double to triple to catch him,” a former staffer with the RPOF told us by phone.
With Vanderlay finishing out the summer on a less than impressive note, it will be interesting to see how she handles a serious competitor. She still has connections and the benefit of running campaigns before… but will that be enough?
Stay tuned for more updates on this campaign, it is going to be a barn burner.
Jacob Engels, is the Founder of East Orlando Post & Seminole County Post. He is a seasoned political operative who has led numerous statewide political groups and has worked on several high-profile local, statewide, and national races. Jacob has been interviewed on national television & radio programs, with his work having been featured in the Orlando Sentinel, New York Times, Washington Post, Miami Herald and other publications nationwide. He can be reached at firstname.lastname@example.org