Get to Know Bobby O


Representative Robert “Bobby” Olszewski (Ol-shess-key) is proud to call West Orange County home. Rep. Olszewski is a former Commissioner for the city of Winter Garden.  He has lived in District 44 since he was two-years old growing up in the Orange Tree neighborhood of Dr. Phillips where he was a product of Orange County Public Schools (OCPS).


Bobby learned the value of education and integrity from his parents. His late father Bob was a former Captain in the United States Army and the Electrical Engineer for OCPS as well as a former Dr. Phillips Little League president and charter family member of the Dr. Phillips YMCA.  His mother Rosie was a public school English teacher, formerly at West Orange High School and currently at Dr. Phillips High School, however, she retired after 30-years with OCPS in June of 2016.


Much of Bobby’s childhood was spent playing sports with his brother Matt, a Florida House District 44 resident, who is a former Orange/Osceola County State Attorney and a practicing lawyer. Bobby’s wife Allison (West), a lifelong Orange County resident, is an OCPS Writing Coach and Teacher at Independence Elementary in Horizon West, previously serving at Spring Lake Elementary, where she won Teacher of the Year, and at Palmetto Elementary, helping move the school from a “F” to an “A” in one year.


Bobby and Allison volunteer at the Basilica of the National Shrine of Mary, Queen of the Universe and attend both Holy Family Church in Dr. Phillips and Resurrection Church in Winter Garden. Bobby and Allison additionally donate their time, treasure, and talents to numerous West Orange and Central Florida nonprofit and community service organizations.  Bobby and Allison are the proud parents to their nearly 2-year old daughter Reagan. 

Rep. Robert “Bobby” Olszewski is committed to our community through his service:

- Former Commissioner, City of Winter Garden
- Orange County Community Action Board Chair
- Roper YMCA Family Center Board Chair
- Roper YMCA Family Center Scholarship Campaign Chair
- MetroPlan Orlando Municipal Advisory Committee Vice-Chair
- MetroPlan Orlando Regional Leadership Council
- Florida League of Cities (FLC) Finance, Tax, and Personnel Committee Vice-Chair
- West Orange Chamber of Commerce Board of Directors
- West Orange/South Lake Transportation & Economic Development Task Force Board
- Winter Garden Squeeze Advisory Board for Florida Collegiate Summer Baseball League
- University of Central Florida (UCF) Knight for Life Alumni Association Member
- Knights Advocate UCF Alumni Government Relations Committee
- Full Sail University Sports Marketing and Media Advisory Board
- Florida League of Cities (FLC) Growth Management & Economic Affairs Committee
- Tri-County League of Cities Central Florida Advocacy Committee
- James Madison Institute Central Florida Board of Advisors
- Leadership West Orange Graduate
- BusinessForce Central Florida Political Leadership Institute Graduate
- Orange County Public Schools (OCPS) Leadership Orange Graduate
- Advanced Institute for Elected Municipal Officials (FLC) Graduate
- Institute for Elected Municipal Officials (FLC) Graduate
- Winter Garden Citizen’s Police Academy Graduate
- Winter Garden Police and Fire Pension Board
- OCPS Montessori of Winter Garden Charter School Board
- Downtown Athletic Club of Orlando Board
- Winter Garden Heritage Foundation Board
- Pet Alliance of Greater Orlando
- The Garden Theatre
- West Orange Habitat for Humanity
- Matthew’s Hope
- Home at Last of West Orange County
- East Winter Garden Community Development Corporation
- Bethany Christian Services
- JMJ Pregnancy Centers
- Rotary Club of Winter Garden
- Rotaract Club of Metro Orlando
- Florida Citrus Sports
- Tiger Bay Club of Central Florida

Bobby is truly homegrown receiving his education from Dr. Phillips Elementary for kindergarten, St. Andrew School in Pine Hills through the fifth grade, and Westridge Middle School.  After graduating from Dr. Phillips High School he earned an undergraduate double major from the University of Central Florida in Radio/Television (B.A.) and Organizational Communication (B.A.), as well as two master’s degrees in Management (M.S.) from Embry-Riddle Aeronautical University, and Corporate Communication & Technology (M.A.) from Rollins College. Bobby also earned a Ph.D. in Business Administration from Northcentral University.

Bobby is a business owner leading the Emerson Management & Consulting Group, Inc. as Managing Principal. He has almost 20-years of leadership and organizational management experience specializing in strategic partnerships, business planning, and economic development.


He has held influential leadership positions within numerous organizations and agencies as these opportunities have offered him the opportunity to work and partner with a wealth of outstanding leaders, brands, and companies in a variety of diverse industries throughout the United States. Bobby additionally serves as an Adjunct Professor, teaching management, business, communication, and marketing courses for many local colleges and universities both in the classroom and on-line, having taught thousands of students throughout his career.

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Political Advertisement paid for and approved by Robert “Bobby” Olszewski,
Republican, for State Representative, District 44

Robert “Bobby” Olszewski
1130 Copenhagen Way
Winter Garden, FL 34787
Telephone: 321.217.8687