The Watchdog
Many people in Key West know me as the Jeep rental guy, or the auto repair guy. For years, I played by the rules: I stayed neutral, I focused on my customers and my employees, and I kept my head down. In business, you can't afford to alienate half the town.
But I've learned that there are times when silence isn't neutrality — it's complicity.
My ties to Key West didn't start in 2014; they started in 2011, when I bought a small Jeep and RAM dealership in Michigan City, Indiana. Michigan City was on the verge of being dropped from the Key West based Superboat Race circuit. The loss would have been devastating for Michigan City, as their entire summer festival was built around the annual Superboat races.
The Michigan City Tourism board was looking for sponsors. I secured RAM Trucks as a sponsor, brokered a meeting between the Michigan City tourism board, the Blue Chip Casino, and Key West's own Superboat race promoters. The meeting was in Key West. The end result: a five-year contract that kept racing alive and saved the summer waterfront festival. I made many Key West friends during their annual visits to Michigan City. While everybody else was talking, I got busy getting things done. I got the right people in a room and hammered out a win-win deal. That's what I understood business to be all about.
But I've also seen the side of politics that doesn't build — it only takes.
I spent seven years, 1997 to 2004, locked in a brutal eminent domain battle in Illinois against a mayor who used his office to line his own pockets. I didn't have political connections; I had the truth. I fought a "quick-take" legislative bill sponsored by the state's most powerful politicians, and I won — not because I was a "political operative," but because I refused to let the big shots bully me or my neighbors.
That fight led me into the belly of the beast. I've been in the backrooms and the boardrooms of local, state, and even federal election campaigns. I've sat in rooms where self-styled "progressives" spoke with genuine, venomous hate for half the country — people who find joy only when their opponents are suffering. I have zero tolerance for people who build their careers on hatred, and I have even less patience for those who claim to be "victims" while they dismantle the communities they invaded.
I know what a predator looks like. I know what a political machine looks like.
I have seen some of the ugliest things this world has to offer. In 2004, with four children of our own to raise, my wife and I took in five children from a broken, drug-addicted home, including a blind girl and a boy shattered by trauma. Nieces and nephews from a half-brother I wasn't raised with. We didn't turn our backs. We fought for their health, education and future. Today, those children are thriving adults. We did the right thing, even when it was the hardest thing.
I'm telling you this because you deserve to know who is behind this site. I am not a political hack. I'm just a regular guy.
Having been involved in politics I know who Chris Massicotte is and who he isn't. He's not just a political opponent; he's an invasive species. Chris has over 20 years experience at the highest levels of liberal, progressive national and international political advertising campaigns. Chris remains a partner in the attack ad firm DSPolitical to this day. He is a man who thrives on the unhappiness of others, and he is methodically working to change Key West into his worldview, rather than let Key West be Key West.
I've survived the some of the worst this world has to offer, and I'm not going to let this island be dismantled by a man who hates half the people he's supposed to serve. I'm a regular guy who's seen the Good, the Bad, and the Ugly side of politics — and I'm here to make sure the ugly side doesn't take root here.
"If you like what political activists like Chris Massicotte have done to the United States and the United Kingdom over the last 20 years, you are going to LOVE what he and his Gang of Four have in mind for Key West and the Florida Keys for the next 20 years."
Evidence Comparison
What he shows Key West
He claims to be an accountant.
He markets himself as an auditor.
He touts his time at PricewaterhouseCoopers — the world's second-largest and most prestigious accounting firm — as the gold standard of his experience.
He highlights his Master's degree in Government Administration as his primary qualification.
He implies these credentials make him uniquely qualified for the Key West Commission.
He downplays his Washington D.C.-based 22-year career in the high-stakes world of divisive political messaging through social media and data mining, where he is recognized as a top-level innovator.
The Python's Real Colors
28 years ago he achieved a BS degree in accounting.
No evidence of CPA certification.
No evidence of continued professional education in accounting.
He identifies as an IT auditor — a distinct role from a financial auditor.
No mention of his tenure at PWC on his professional LinkedIn page — a firm he markets as the "gold standard." Why?
No evidence of employment in a role utilizing his Master's degree in Government Administration.
Can you spot the snake in the grass?
He is qualified to pursue public office because he got an accounting degree 28 years ago, but did not pursue a career in accounting?
Would you trust this guy to prepare your tax returns?
He has a Master's in Gov't Administration, yet he has no work experience inside any city hall or public office in the country, and leaves this completely off his resume?
If this guy applied for the job of City Manager, would he make the cut — given his complete lack of experience?
He has a stellar, lifelong Washington D.C.-based career in the highly divisive world of winning political campaigns through digital advertising — recognized as one of the all-time greats — yet he downplays himself as just a small-town political consultant? Why?
Investigative Dossier
From D.C. Power Player to Key West Candidate. A breakdown of the career he doesn't want you to know about.
The Credibility Check
In 2015 Massicotte was named a "40 Under 40" leader in D.C. political consulting. This accolade confirms his status as a nationally recognized expert in progressive digital messaging — a far cry from the "small town accountant" image he presents to Key West voters today.
Key Takeaways from the Press Release
"Professional accounting's loss was professional politics' gain —
Massicotte never looked back."
Ed: Massicotte entered divisive politics in 2005 at age 29.
Congratulations Chris!
🎉Bravery Above and Beyond the Call of Duty: The D.C. Ad Grant Award
Chris Massicotte, the mastermind behind DSPolitical, has been named the top recipient of his own firm's 2024 Ad Grants program. The award? A recognition of "bravery above and beyond the call of duty" in his unsuccessful campaign for Monroe County Commissioner.
"I never thought I would win, and I am so, so honored by this award," Chris said, reportedly choking back tears of joy.
"I want to thank my business partners, my employees, and all the 'little people' who continue to operate the multi-million dollar political ad agency I spent 20 years building at DSPolitical."
DSPolitical is the world's leading political ad agency dedicated to promoting progressive and liberal messaging.
Click here to see all our proud 2024 award winners!Ed: They aren't local — they are the D.C. machine that spends millions to influence elections across the country. Chris isn't just an employee — he's a partner. He helped build this firm. He ran this firm. And then his firm handed him a grant to run for office. If he's this comfortable awarding himself insider deals in broad daylight — and issuing a press release to brag about it — ask yourself: what does he intend to do with a seat on the Key West Commission?
The Python is a political animal that adheres to the law of the jungle: it shows no mercy, consumes everything in its path, and is fueled strictly by partisan ambition.
Evidence File
Three roles. Three organizations. One consistent pattern.
DSPolitical
Catalist
The Strategist
The Infection Map
Chris Massicotte moved to Key West and began spreading his DC political hateful venom almost immediately. This is the infection map.
Chris Massicotte
Python Massicottus (DC variety)
Republicans make my skin crawl.
The Real Story
Twenty years D.C. political advertising executive; built the pre-eminent progressive ad agency — DSPolitical. Catalist. Soros money. Now running for Key West office — and he brought his venomous hidden agenda with him.
Sam Kaufman
Python Kaufmanicus
Sammy did a bad, bad thing.
The Real Story
A long-serving commissioner. Once a good man. My neighbor. But he has been bitten. Political venom flows in his veins.
Flashback September last year. Sam kicks to the curb the highest qualified Planning Board member — a man who served as attorney to the Planning Board for 6 years. Sam installs his novice political partner Sarah Compton. Why? She is eager. She wants to learn. She needs exposure. Sweetheart backroom political deal.
Sam put personal political ambitions before the people's business. He crossed a line. Voters, do Sam a favor. Send him home to his family and his law practice. He desperately needs anti-venom therapy.
Sarah Compton
Python Eagerbeaverous
Eager Beaver has big dreams.
The Real Story
Sarah Compton is not a Key West success story. She is a Chris Massicotte plant story. Relatively new to town, new to politics, new to who's who in this small town — but eager. Sarah is very eager.
Sam Kaufman made a sweetheart backroom deal to push Sarah's political career along. Sam kicked the most qualified Planning Board member to the curb — a man who served as the board's attorney for six years — and installed questionably qualified Sarah in his place. She must be a fast learner though. After attending two, count 'em two, Planning Board meetings, Sarah decided, all on her own, to file for the big leagues.
Sarah's excited to be part of the Gang of Four looking to take control of the Board of Commissioners to bring their liberal progressive change to Historic Key West — which somehow, someway, was able to survive 200 years without Sarah Compton in charge.
Why Sarah? Why not somebody more qualified, more connected to the city? Because Sarah will do what she is told to do, say what she's told to say, and most importantly Sarah will vote the way her political mentors tell her to vote.
The Verdict: Do Sarah a favor. Send her back to reality.
Bobi Lore
Python Fibberocious
I will not tell a lie.
I will not tell a lie.
I will not tell a lie.
I will not tell a lie.
I will not tell a lie.
I will not tell a lie.
I will not tell a lie.
I will not tell a lie.
I will not tell a lie.
I will not tell a lie.
The Real Story
The Python needed a candidate for District 2. Bobi bit the apple, though the geography didn't fit. Bobi lived in District 1 — at 119 Simonton, his home since 2019. To run, Bobi had to move. Pronto.
The Web of Lies
The Verdict: A campaign founded in lies. Lies about where he lives, lies to the bank to obtain a favorable rate on his “former” home in D1; Lies to the DMV as he illegally postpones updating his DL to his D2 rental address for over 7 months. This is no way to start a campaign promising integrity.
With malice towards all — keep Key West safe from invasive species from DC like these four. Vote August 18th.
Sarah Compton for Key West Office
#all4all4keywest — all four names. one post. one slate.
Jeffrey Siegel
"Working on our slate endorsements" — first to make the big announcement, before Bobi went house hunting in District 2.
Lear before you vote
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