Olszewski says 'time was right' to run for county seat

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  • | 11:46 a.m. September 9, 2015
Olszewski says 'time was right' to run for county seat
Olszewski says 'time was right' to run for county seat
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Olszewski OC D1 File

WINTER GARDEN — District 3 Winter Garden Commissioner Bobby Olszewski said there was no better time than last week to go for a constant goal — serving as District 1 Orange County commissioner.

“With my family’s history and my commitment to public service, looking at all that we were able to accomplish in Winter Garden, the time was right to be able to give back even more to Orange County,” he said.

Olszewski grew up in the Orange Tree neighborhood of Dr. Phillips, right next to Dr. Phillips Elementary, where his parents — Bob and Rosie — provided an amazing example of commitment and service for Olszewski and his brother, Matt, he said.

“My family was one of the original season-ticket holders for the Orlando Magic,” Olszewski said. “It was always a special time for my dad, my brother and I to attend Magic games together.”

But baseball was the constant sport for Olszewski as a child, given his father’s roles in Dr. Phillips Little League, from coach and umpire to president. At Dr. Phillips High, he became the backup catcher to current Atlanta Braves catcher A.J. Pierzynski and a teammate of retired MLB outfielder Johnny Damon. Joey Fatone of ‘NSYNC and Florida State Rep. Randolph Bracy were in his graduating class, he said.


Olszewski’s wife, Allison, and his other family members have been the most integral people in his life. Meeting Allison was part of a series of unexpected turns for Olszewski, none bigger than the death of his father from a hip-replacement surgery in 2003, the same year Olszewski moved to Winter Garden.

“We were never expecting that result, and that has truly been the greatest tragedy of my life,” he said. “I know in my heart things happen for a reason. But to lose my dad at such a young age, I don’t know whether I have the perfect answer for why that happened.”

But Olszewski believes everything happens for a reason, and Allison persisted in generous help to Rosie when Rosie returned to teach at Dr. Phillips High, he said.

“I heard all these stories about this Allison, who was so nice and doing so much for me, so sweet,” Olszewski said. “Well, my mom decided to go back to Stetson University to get her master’s degree. Allison was earning her undergraduate degree at Stetson at the same time.”

Allison attended Rosie’s graduation, where she met Olszewski.

“I feel that is very special, because it seems like my dad brought us together, and as they say, the rest is history,” he said.


Themes from Olszewski’s upbringing are easy to spot in his current life. His passion for sports has gone from being an agent for PGA golfers to supporting the Winter Garden Squeeze and efforts to build a stadium near historic downtown. His Catholic heritage remains present in his and Allison’s faith, attending services each week. His learned commitment to service has grown to involvement with many community organizations, including the Roper YMCA Center, where he recently became chairman of the board of directors.

“When I’m not serving the people, you can find me working out at the Roper YMCA, as I am there every morning at 5:30 during the week and will grab an occasional workout on the weekend, if I’m not busy,” he said. “My wife and I volunteer at the Basilica of the National Shrine of Mary, Queen of the Universe on Sundays, in addition to attending Mass at Resurrection Catholic Church in Winter Garden or Holy Family Church in Dr. Phillips.”

Faith has strengthened their resolve to serve, primarily the Pet Alliance of Greater Orlando, based on the love they have for their three beagles, he said.

“I am a true softy when it comes to animals,” Olszewski said. “Unfortunately, we just lost our 14-year-old beagle this year. It pains me to this day, because our beagles are like family members.”

Although Olszewski said politics become the hobby of any elected official, he and Allison find time to try different restaurants and spend time with each other’s family, such as on a boat at Allison’s family’s Clermont lake house.

“My wife is truly my best friend,” he said. “I can’t think of anyone else I would rather spend my life with than her, because we truly complement each other in so many different ways and are a great team. God knew what He was doing when He brought us together.”

Contact Zak Kerr at [email protected].


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