Collier County School Board member Kelly Mason appeared in a new advertisement, paid for by the Florida Democratic Party, where she supported Democratic gubernatorial candidate David Jolly in the general election and attacked Republican nominee Byron Donalds.

The 30-second spot, released on October 7, shows Mason claiming personal knowledge of Donalds and his wife Erika from their time serving together on the board of Mason Classical Academy. She alleges both Donalds sought personal profit from charter school management and attempted to intimidate her during those years. Mason states she previously supported Gov. Ron DeSantis but will vote for Jolly in the general election.

The Jolly campaign framed the endorsement from Mason, a Republican, as an indication of Jolly’s cross-partisan appeal. In reality, Mason’s endorsement is just the latest episode in a long pattern of opposition to Donalds. She previously backed and campaigned for gubernatorial hopeful James Fishback against Donalds in the state's August primary. Notably, Mason and Fishback shared the same attorney in Anthony Sabatini, a Lake County Commissioner and former state lawmaker, that represented Mason in her July 2026 lawsuit against Donalds and worked for Fishback in a ballot access dispute earlier this year.

Mason's dispute dates back years. Mason, then known as Kelly Lichter prior to her divorce, and other board members filed a lawsuit against Erika Donalds and others over alleged attempts to seize control of Mason Classical Academy. In 2020, while Donalds ran for Congress, Mason filed an ethics complaint alleging he had lied in license and appointment applications. In the July 2026 lawsuit, she claimed Donalds confronted her aggressively at a Naples grocery store in 2022, an encounter captured on video. She voluntarily dismissed the suit in September 2026, just weeks after Fishback's third place finish in the primary. Donalds described the encounter as an effort to resolve litigation directly and called the lawsuit baseless and politically motivated.

Fishback immediately highlighted the lawsuit on X the next day, further advancing campaign rhetoric of Donalds being a "violent criminal". In a post on X, he called the incident an "assault" and said Donalds "chimp[ed] out" against Mason.

The video of the encounter shows Donalds and Mason in a verbal confrontation, including him telling her to "stop the lawsuits," but does not show any physical contact between the two. Donalds defeated Fishback and other GOP challengers by wide double-digit margins on August 18 to win the party's nomination.

Mason’s now ex-husband Nicholas Lichter has been arrested for numerous drug crimes, including a 2013 arrest for cocaine possession and possession of drug paraphernalia. Multiple 2024 incidents resulted in further criminal charges against Lichter, including possession of controlled substances, use of drug paraphernalia, a probation violation, and a driving-while-license-suspended charge. The arrests raise questions about her personal associations at the time she was involved in education advocacy. Jolly, a self-styled moderate, is leveraging the ad to attempt to court DeSantis voters disillusioned with Donalds and the Florida Republican Party, as well as seeking Fishback supporters that feel spurned after his primary loss.

The general election race between Donalds and Jolly has just four weeks until Election Day. Democrats are hoping that Mason’s defection to Jolly’s camp is emblematic of a broader trend of Republicans supporting the Democratic nominee. In reality, Mason’s support for Jolly seems to stem from a years-long personal vendetta, not from substantive policy disagreements.

Despite growing Democrat hopes of a blue Florida or a major November wave, recent polling and strong early ballot returns do not favor a toss-up narrative. Most signs point at the GOP retaining the Sunshine State in November with limited statewide gains for Democrats.