City Commission Work Session Discusses Global Billboard Swap Deal

The Winter Park City Commission held a work session on November 13, 2025, at 3:30 PM to discuss a global settlement agreement regarding the removal of all billboards in the core of the city, with one exception. Representatives from Clear Channel Outdoor, Lamar Advertising, and OUTFRONT Media presented a Memorandum of Understanding (MOU) that outlines a series of billboard removals and relocations. The Commission expressed consensus to move forward with the proposed swaps.

Discussion Items

• Global Billboard Swap Deal: City Manager Randy Knight presented the global settlement, noting that Clear Channel, Lamar, and OUTFRONT Media have signed an MOU agreeing not to compete for future billboard locations. The deal involves removals and relocations as follows:
  • Clear Channel: Removing four billboards (1873 and 2095 W. Fairbanks, 2522 Aloma Avenue, and one on Wymore Road next to the fire training facility). In exchange, Clear Channel will relocate the Wymore billboard about 300 feet south to meet the 1,000-foot separation requirement for digital billboards along I-4, and build a second digital billboard at the Nort Northam property (2600 W. Fairbanks). The new billboard at 2600 W. Fairbanks will be digital facing westbound I-4 and static facing eastbound I-4.
  • Lamar: Removing the double-sided digital billboard at 1621 Lee Road. In exchange, Lamar will construct a new billboard at 909 N. Wymore Road along I-4, which will require annexation of a portion of that property.
  • OUTFRONT Media: Removing three billboards at 2090, 2145, and 2431 Aloma Avenue in exchange for a digital billboard at 1885 Dartmouth Avenue. The area is currently outside city limits and will require annexation of four properties between the existing boundary and the proposed site.
• Mayor's Request: Mayor Sheila DeCiccio asked Clear Channel to consider removing an additional billboard on 17-92 at Gay Road, but Meredith McKenna from Clear Channel responded that it is part of an existing agreement and they cannot commit to its removal. Mayor DeCiccio requested McKenna ask her company to include it in the deal.
• Annexation Process: Attorney Langley explained the annexation process, and discussion followed. Orange County must approve annexation agreements. Matt Howard of Lamar offered to assist in obtaining county approval.
• Next Steps: Staff will bring annexation ordinances and city property swap ordinances to the Commission for consideration at future meetings. The parties must obtain approval from Orange County and property owners through voluntary or involuntary annexation.

Key Outcomes

• Commission Consensus: Mayor DeCiccio stated there is consensus from the Commission to move forward with the global billboard swap deal.
• No Vote: As a work session, no formal vote was taken. The direction to staff is to proceed with the annexation and ordinance processes.
• Meeting Adjourned: The meeting adjourned at 4:20 PM.

Note: The raw transcript included unrelated content (a police strategic plan presentation), which appears to be from a different meeting. The agenda and minutes consistently describe the billboard swap discussion as the sole agenda item.