Ozzie Giglio is a founder and CEO of Windy City Motorcycle Company. Mr. Giglio founded WCMC in 2000. After creating WCMC, Mr. Giglio acquired the first dealership. It had revenues of $8 million, 14 employees and was housed in 16,000 ft.². Over the course of the next 20 years, Mr. Giglio would conduct 17 business acquisitions (both stock and asset) and more than 20 Real Estate deals to grow WCMC to nearly $180M in revenue with over 300 employees and occupy approximately 500,000 sq ft of retail space. Mr. Giglio also developed over 200,000 sq ft of commercial space (along with construction financing and mortgage end loans) and executed multiple TIF agreements with several municipalities. WCMC operated multiple Harley-Davidson Dealerships in Chicagoland and greater Milwaukee. WCMC also sold Triumph and KTM motorcycles. In addition to business, development and Real Estate transactions, Mr. Giglio also negotiated multiple commercial loans, revolving lines of credit, private debt and floor plan credit arrangements with both manufactures and commercial lending institutions. As the powersports marketplace contracted and demand for motorcycles changed, Mr. Giglio successfully executed multiple consolidations and sales transactions to reshape the Chicagoland marketplace, redefine the WCMC brick & mortar footprint and reconstitute WCMC to position the Company for sale. The business along with the attending Real Estate sale occurred in September 2025.
Prior to creating WCMC, Mr. Giglio was employed by Equity Group Investments and related entities, a Sam Zell Organization. While with the Zell organization, Mr. Giglio participated in numerous transactions, including those involving multiple real estate deals, the acquisition of Schwinn Bicycle Company, private and public debt financing of over $500M, the acquisition of the Executive Life Insurance portfolio of real estate and its related debt structure and participated in the formation of three Zell-originated Real Estate Investment Trusts (REIT) to include Manufactured Housing Communities, (NYSE-MHC), Equity Residential Properties Trust (NYSE-EQR) and Equity Office Properties (NYSE-EOP). Upon its creation, Mr. Giglio became Senior Vice President-Business Development for EQR. At the time of his departure from EQR, the Company had over a $9B market cap.
Prior to joining the Zell organization, Mr. Giglio practiced Corporate Law with Jones Day, Katten Muchin, two the nation’s largest and most prestigious law firms, where he concentrated on all aspects of Corporate Law. Mr. Giglio is licensed to Practice Law in Illinois and Texas.
Mr. Giglio sits on the Board of Directors for INCENTCO, a real estate support business, The Darley Industries, Defense Advisory Board, a 115 year-old privately held company in the Fire, Emergency and Defense Industries, Radiant 1, a Chicago-based Marketing firm, Good Sports, a Boston based charity that provides sporting equipment to children throughout U.S., The Alex Pissios Family Foundation, The University of Chicago Biological Sciences Division Board, Illinois Motorcycle Restaurants (Alley 64-Palatine) and an Advisory Board at Columbia University Medical Center. Mr. Giglio is a former member of the Harley-Davidson® Financial Services Advisory Board, and former President of the Harley-Davidson Dealer Advisory Council.
Mr. Giglio is a retired United States Navy Captain. CAPT Giglio served as a Naval Intelligence Officer and Naval Parachutist, specializing in Humane Intelligence (HUMINT), Joint Special Operations and Navy Special Warfare. From September 11th, 2001, through December 2016, CAPT Giglio forward deployed on multiple tours with Joint Special Operations Task Forces throughout the Middle East, including in Iraq in support of Operation Iraqi Freedom (OIF), Afghanistan in support of Operation Enduring Freedom (OEF), and to a variety of other theaters throughout the Globe in support of Maritime Intercept Operations (MIO). CAPT Giglio then served at the Pentagon for the Under Secretary of Defense for Intelligence (OUSDI) as the Special Intelligence Operations Officer, until his Military retirement in September 2020.
Education
- JD with Honor from DePaul University College of Law
- Admitted to practice Illinois
- Admitted to practice Texas
- BA with High Distinction and Honor from Valparaiso University
- Graduate of Fenwick HS, Oak Park High, Illinois
Other Interests
Avid motorcycle rider, Volunteer Fire Fighter, Golf, Ice Hockey
Mr. Giglio is married to the former Jill S Palleson of Naperville, IL and they reside in Hinsdale, IL with their twins Ronin and Jorie.