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Anne Mooney / December 22, 2014 / Read & Input Comments

On December 17, Steven J. Leary announced his resignation from the Winter Park City Commission, effective March 15, 2015, which he was required to do to launch his mayoral campaign. Leary will continue to serve as Commissioner, Seat #1, until March 15. If he is elected, Leary will assume his post as mayor at that time. If he loses the mayoral election, Leary will officially resign from the Commission. 

Brewer vs. Shambeck for Leary’s Commission Seat

Either way, as it stands now, Leary’s current seat on the Commission will be filled either by former Mayor and Commissioner Gary Brewer or by his opponent, political newcomer Willow Shambeck – to date, the only two who have declared their intentions to run for this seat.

But There’s Still Time

According to Lucy Melendez of the Orange County Supervisor of Elections Office, candidate qualifying begins December 29, 2014 and lasts until January 6, 2015. During that time, additional candidates may file to run either for Commission Seat #1, currently held by Leary, or for the mayoral race. 

More Candidates Means February 10 Primary

Three or more candidates for any seat would result in a primary election, to be held on February 10, 2015. If any one of the three opposing candidates in the primary receives 51 percent or more of the votes, that candidate wins the election then and there. If no one receives 51 percent in the February primary, the two candidates with the highest vote counts run against each other in the March 10, 2015, election. 


February 10 Primary Changes Voters’ Schedule

A primary would significantly change the dates for voters as well as for candidates. A chart of events is below. Please note: in the event of a February 10 primary, Voter Registration would close January 12, 2015.

2015 Election Schedule — Mayor and Commission Seat #1

Mayoral Donors Generous

The latest Campaign Treasurer’s Report Summaries show that political support has been robust throughout the holidays. Leary’s contributions totaled $21,700 as of an amended December 5, 2014, report. Of that amount, five of the most recent donations came from controversial Ravaudage developer Daniel Bellows and his partner, attorney Robert Saltsman. 


Mackinnon Outstrips Leary

Leary’s opponent, retired Judge Cynthia Mackinnon, has so far raised in excess of $95,000. Her donations come from a somewhat broader base of Winter Park residents. That said, Mackinnon’s campaign began its efforts earlier. Leary’s campaign is expected to ramp up once the holidays are over.


Commission Donors Lag

In contrast, Brewer recently reported donations totaling $7,700 and Shambeck reported a total of $4,000 in contributions. These are early days, however, and things are sure to heat up in the new year.


Campaign Treasurer’s Reports can be found on the City of Winter Park website at

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