A Campaign of Contradictions: Why Winter Park Can Do Better Than Cynthia Mackinnon

    A campaign consultant on 5th Avenue in NYC, repetitive use of racially insensitive terms and violation of contribution rules for a sitting judge are just the tip of the iceberg in the former judges campaign of dishonesty.


    By Jacob Engels


    With just under two weeks until voters in Winter Park go to the polls and select their new Mayor, candidate and former Judge Cynthia Mackinnon is continuing to be dishonest and untruthful with citizens. Mackinnon, a who sat on the bench for over 20 years is married to Alex Mackinnon, a local developer.


    Both Steve Leary, a current Winter Park Commissioner and Cynthia Mackinnon have traded barbs several times during an increasingly contentious campaign. However, it has consistently been Mackinnon who has been been caught having trouble with operating an honest and truthful campaign.


    Developers Love My Opponent & He Wants To Destroy Winter Park’s Heritage…


    Early in her campaign for Winter Park, Mrs. Mackinnon attacked Leary for being an advocate of unreasonable development in Winter Park, and someone who was more concerned about profiting than preserving the heritage of Winter Park. This claim was quickly rebuked when observers quickly pointed to the fact that Leary has been involved in restoring and preserving historical buildings for years.


    The Leary campaign followed up with a video highlighting these projects, which was quickly fact-checked and proven to be truthful.


    Steve Leary is in bed with special interests… but not really.


    Then, having not learned from her first foray into gutter politics, Mackinnon claimed that Leary voted on an item before the City that was tied to a campaign contributor of his. The Winter Park Maitland Observer bought Mackinnon’s talking points hook, line and sinker – and then her campaign used the article in a mailer to potential voters…claiming it was proof-positive that Mr. Leary was in bed with special interests.


    Not too long after the article and mailer were released, the newspaper issued a retraction after looking further into the matter – announcing that they had mischaracterized the vote and potential conflict of interest. But Mackinnon continued to use the sloppy faux journalism in stump speeches and social media to attack her opponent. For the second time in a relatively short campaign, Mrs. Mackinnon did not let the truth get in the way of her tabloid’esque attacks on the Leary campaign.


    Federal Campaign Contribution Violations & Amnesia…


    They say bad things come in threes, and for the Mackinnon campaign that was certainly the case when she was asked about her contribution to Barack Obama and Val Demings in 2012…while she was still barred from donating to campaigns as per state law – as she was still in a period of eligibility that bars judges from engaging in inappropriate political activity.


    The Code of Judicial Conduct applies to senior judges, pursuant to its Application provisions:


    B. Retired/Senior Judge


    A retired judge eligible to serve on assignment to temporary judicial duty, hereinafter referred to as “senior judge,” shall comply with all the provisions of this Code except Sections 5C(2), 5E, 5F(1), and 6A.


    But the provisions dictating what a retired eligible judge can’t do in regards to political activity do not fall under the exempt Sections 5C(2), 5E, 5F(1), and 6A.


    The Code of Judicial Conduct prohibits a judge from making a contribution to a political candidate:


    Code of Judicial Conduct, Canon 7. A Judge or Candidate for Judicial Office Shall Refrain From Inappropriate Political Activity


    A. All Judges and Candidates.


    (1) Except as authorized in Sections 7B(2), 7C(2) and 7C(3), a judge or a candidate for election or appointment to judicial office shall not:


    (e) solicit funds for, pay an assessment to or make a contribution to a political organization or candidate, or purchase tickets for political party dinners or other functions.


    First, Mackinnon claimed that she did not recall or remember the $2,000 in donations she made to the Barack Obama campaign and a linked campaign committee for the president’s 2012 re-election bid. FEC reports also show she dolled out $250.00 to Val Demings doomed congressional bid against Dan Webster.


    FEC Individual Contribution – Cynthia Mackinnon


    We have also heard, that at several campaign events Mrs. Mackinnon has claimed it was a donation made by her husband out of a joint checking account, insisting she was not at fault. But again, Mackinnon’s claims did not stand up to the smell test.


    While a sitting judge, her husband Alex, according to several FEC filings made multiple contributions…never listing a joint checking account or Mrs. Mackinnon on any documents.


    FEC – Alex & Cynthia Mackinnon Contributions


    It would seem that Mrs. Mackinnon, a 20 year veteran of the judiciary would have a tighter grasp on laws applying to retired and senior judges and more clear recollection of several high dollar campaign contributions…but I guess not.


    And Then There Was Negro Town…


    Most recently, Mackinnon again raised eyebrows when she began publicly referring to the West Side of Winter Park as “Negro Town”, and it’s residents as “those people.”


    Debuting her racially charged campaign talking points during an Orlando Sentinel editorial board interview, Mrs. Mackinnon has doubled down and continued using the racially insensitive term in subsequent campaign appearances and debates.



    Mackinnon has argued that the West Side of Winter Park was platted and referred to as “Negro Town,” both historically and during her lifetime. However, a documents we obtained from the City of Winter Park and Orange County contradicts Mackinnon’s claims and begs to question why the former judge remains focused on addressing Westside residents as “those people” and inhabitants of “Negro Town.”


    The document, which addresses plats in Winter Park going back to 1885, is missing any reference to a “Negro Town” settlement.


    Plats of Westside Winter Park Since 1885


    Current Winter Park Mayor Ken Bradley told the East Orlando Post that he believes Mrs. Mackinnon’s comments are both racially insensitive and inflammatory.


    “I would like to state for the record that I do not agree with candidate Cynthia Mackinnon’s use of racially offensive and inflammatory terminology in describing Winter Park’s Westside.


    Her comments that she didn’t want to “walk in ‘strange’ neighborhoods, ‘those people’ when referring to African American neighborhoods, “us ‘White people’ and ‘Negro Town’”— are careless, insensitive, and especially incendiary in light of recent racially volatile national events. Claiming to be civil and one who will unite, but using language like this is insensitive and insulting to the 29,000 citizens of Winter Park. There are no official plats going back to the late 1800s that use her terminology.


    We all have worked much too hard to unify our city and do not want our city’s reputation to be tarnished nor give the idea that her words are acceptable in any manner.”


    Mayor Bradley endorsed Mackinnon’s opponent Steve Leary on February 26th, citing his need to support a candidate who has engaged in an honest, positive and truthful campaign. Ouch…


    Mackinnon Retains Madison Avenue & South Florida Consultants…


    Preserving local heritage, stymieing new development, standing up to special interests and working for and with the citizens of Winter Park have all been focal points of the former judges campaign.


    Yet, she picked a 5th Avenue consultancy out of New York and a South Florida based political consultant to run her campaign. Many times, the way a candidate operates and staffs a campaign can be indicative of how said candidate would govern when/if they are elected.


    So, if Mackinnon were to be elected, would she first look to high priced vendors and companies on 5th Avenue…or would she work to help local businesses and contractors flourish?


    Winter Park Deserves Better…


    While I do not know Mr. Leary or Mrs. Mackinnon, what I have seen in this abbreviated campaign is enough for me to reach a conclusion about at least one candidate.


    Mrs. Mackinnon has not had just one instance of dishonesty, she has had several. Mrs. Mackinnon has engaged in gutter politics not once, but several times. Mrs. Mackinnon continues to refer to the West Side of Winter Park as “Negro Town”, it’s residents as “those people” and its neighborhoods as “strange places.”


    Each of the above mentioned things not only cause me to question if she is the proper choice for Winter Park, it also has me wondering how a former judge who made those appearing in her court swear to tell the whole truth and nothing but the truth can justify such untruthful behavior.


    But hey, we’ve all heard that politics can bring out the worst in people…and we have certainly seen the some pretty questionable behavior from Mrs. Mackinnon in just a few short months.


    Winter Park residents deserve a candidate and potential Mayor who will tell them the truth and nothing but the truth.


    It appears former judge Cynthia Mackinnon is simply not up to the task and that’s a damn shame.


    Jacob Engels, is the Founder of East Orlando Post & Seminole County Post. He is a seasoned political operative who has led numerous statewide political groups and has worked on several high-profile local, statewide, and national races. Jacob has been interviewed on national television & radio programs, with his work having been featured in the Orlando Sentinel, New York Times, Washington Post, Miami Herald and other publications nationwide. He can be reached at info@eastorlandopost.com