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GOP Strategist and Massive Anti-Trumper Rick Wilson ... Teaching Florida Democrats How to Win?

April 3, 2019 - 7:00am
Rick Wilson
Rick Wilson

The ascendancy of Donald Trump in the GOP primary in 2016 caused a rift in the Republican Party. That fracture became a canyon with his ensuing election win, and a vocal Never-Trump faction growing increasingly louder over the past couple of years. GOP strategist Rick Wilson of Florida has been a member of that separatist contingent, if not its leader. 

Recently, Wilson has grown increasingly more antagonistic ... until now it appears he has moved further, going past mere Trump opposition to actually looking to aid the Democrats in Florida. A fairly wild notion for a long-entrenched Republican loyalist.

The political landscape of the state and how it would be impacted by the growing contingent of Puerto Rican transplants has been the focus of speculation for years. While Hurricane Maria caused a great many of the island residents to transplant to Florida in the fall of 2017, what actually took place was a slight acceleration of a long-term exodus. With the economic conditions on the island in a never-ending downward spiral, Florida has been absorbing Boricua pilgrims for more than a decade.

Today more Puerto Ricans live on the U.S. mainland than on the island itself, and the Florida PR population has exceeded one million for some time. Political pundits in the Sunshine State have long expected to see the party power tilt toward Democrats as a result of this ongoing influx. The reason for this was based more on assumptive reasoning than analysis of those who were making the trek to the States.

Wilson has made it clear he opposes President Trump in pretty much every manner one man can possibly oppose him. A regular guest on antagonistic news networks CNN and MSNBC, he also is the author of the stinging book, “Anything Trump Touches Dies,” an immediate resident on the New York Times Bestseller List in 2018. Now he's making the move even further afield of the GOP establishment. In a debate currently waged in D.C., Congress is working on a hurricane relief bill and there have been contretemps between the parties over the amount of additional funding that will go to Puerto Rico.

After an effective verbal agreement on the spending had been reached, Trump hurled in a monkey wrench in the proceeding. The president has called to curtail the spending for the island. Democrats want to keep the amount in place for the continued relief efforts. In a late-night flurry on Twitter, President Trump gave his numerous reasons for clipping the payouts.

This led Rick Wilson to return volley with his own series of tweets. 

However, more than opposing the president’s relief policy, what Wilson delivered was a kind of strategy plan for the Democratic Party in Florida. While he sounds as if he castigated the party for its ongoing inability to be effective, what Wilson is doing in reality is showing the Florida Dems what they've been doing wrong. It is a curious stance, seeing a GOP party planner describing for Democrats a plan on what they need to do to earn those Puerto Rican votes.

Donald Trump
Donald Trump


Click on the links to the tweets and see for yourself. If that's too much clicking, here's Wilson's whole series of tweets, one after the other, laid out like tarot cards in a carnival sideshow:

TWEET NO. 1: "Just a reminder of the why Democrats are holistically terrible at politics. Trump is HANDING you Puerto Rican voters in Florida. On a platter. It's a layup. But the Democrats will do just what they did in 2016: jack. Followed by squat."

TWEET NO. 2: "It'll be another "we got this" Potemkin Village. They'll farm it out to some contractor or group who won't go out, pull the voter file to ID PR registered voters, track down new arrivals from the island to register them, and then do advocacy, messaging, and turnout."

TWEET NO. 3: "Know why Rick Scott and Ron DeSantis won more PR voters than the Dems expected?

"Because they DID THE WORK.

"Put ideology aside. I'll bet you a dollar the FL Dem Party doesn't have a program to do this. I know the DNC, those incompetents, don't."

TWEET NO. 4: "The AUDIENCE is there and primed. But Democrats in-fight, B.S. themselves blue, and pretend that some vague handwave message about Latinx issues will cover it.

"It won't. Stunt casting won't cover for a total lack of org and programmatic work on the ground."

TWEET NO. 5: "Just watch. They'll say, "We have a program and x people on the ground." Reality: They don't have a program, and no one is on the ground doing it, registering, and comms to PR voters except the GOP.

"But they hate Trump. Yeah, and? That doesn't close the deal."

The tone of disappointment and expectation is palpable. This line of directives seems tailored to show the Dems what they need to curry the vote of those new arrivals. This is actually something Wilson has been looking to take place for years now -- all the while it hasn't materialized into the expected windfall for Democrats.

Back in those days after the hurricane, Wilson anticipated a big party swing as a result of the exodus. “If you put an influx of 100,000 Puerto Ricans who vote Democratic eight times out of 10 in the Orlando area, there you go,” he said, predicting the newcomers would foster a resistance to Trump. Wilson’s resentment, however, did not translate effectively.

As I had pointed out at that same time, those Puerto Rican votes were not assured, as a large number of the transplants were registering Independent. Many were from the working and professional classes, and they had been fleeing due to the economic morass created by the Democratic Party stronghold on the island. There was ample opportunity for the Republicans to earn favor from these new residents of the state, I said, and that has in fact paid dividends.

Look over the recent elections in the state since the influx. The expected benefit did not show in 2016, as President Trump won the state in the general election. During the midterm election last fall, when there was a surge of Democratic wins and they took over the House, in Florida the GOP improved its hold across the state. Bill Nelson lost his longtime seat in the Senate, despite hailing from the Puerto Rican-rich Orlando area. Rick Scott edged out the victory in their race, due in large part to his stronger-than-expected performance with the Latino voters.

That Wilson harbors a deep disdain for the president is evident. To see that now transform, though, into a veiled effort to coach Democrats here in the state is a deeper curiosity to behold. 

Brad Slager, a Fort Lauderdale freelance writer, wrote this story exclusively for Sunshine State News. He writes on politics and the entertainment industry and his stories appear in such publications as RedState and The Federalist. 


Trump is a Nazi And gop’ers are a terrorist party. Hysterical!!!!

Rick Wilson was way wrong in 2016 and I predicted in 2016 that Trump would win by a Landslide. I was right. 306 to 222. Even after 3 years, I never get tired of LOL at these NeverTrumper fools and Rick Wilson in particular. In my 50 years of political activity and/or interest, we have NEVER had a President that is as POPULAR within his political party as we have now. 93% of the GOP support Trump. This tells me that Trump will easily be nominated and will win in November by another Lanslide. This time both in the Popular Vote and the Electoral College. Alan Abel Former Vigo County (IN) Republican Chairman

Rick has serious 'unemployment' in his foreseeable future. (One should never "telegraph his moves"..) : Including "Jolly" and "Crist" in this "unholy triumvirate" virtually ensures that !

Rick Wilson is starting to really believe the Socialist's Dream - free EVERYTHING! He's gone delusional!

Too many "anonymous" commenters! Where is your courage? To the nameless and faceless Rick Wilson enablers, the GOP was about to go the way of the Whigs until Donald Trump took the helm. The elitist gate-keepers would rather let the party die than to allow Donald J. Trump to win. Now we have a president in Donald J. Trump that is the envy of freedom lovers worldwide. Thank you President Trump, for being our voice. Time to purge the establishment RINOS from your administration who are persuading you to renege on your promises - build the wall, preserve our Constitutional rights (NO SIGNING ANTI-2nd AMENDMENT BILLS), end the fed, end the Federal "Department of Education," (AKA Propaganda Ministry destroying our children) and RESTORE STATES RIGHTS - a win/win for all Americans, and a sure win for the presidency in 2020! #MAGA #KAGA.

The GOP was born in corruption. It was the GOP that illegally invaded the south and caused over 700K deaths while ushering in the era of big government and overturning the Constitution of the framers and ratifiers from one of independent sovereign states to one of an all powerful central government. Trump has ruled bumpstocks illegal by decree, setting a standard for those who come after him to build upon such usurpations. Reagan ran on ending the ed department, he didn't. No Republican regime has yet to mount a campaign to repeal the 16th amendment and repeal the income tax, roll back the New Deal or The Great Society, Indeed, W added prescription coverage to medicare! Trump continues to add to the deficit which is now 22trillion and growing. So, when you use the term RiNO, what exactly is the high water era of the GOP you are using for a standard to judge other republicans? It's a fantasy. Republicans are what they are- just the co equal branch of the Red and Blue Crime Family cartels. You people had a chance with Ron Paul and you rejected him. Now you reject the sanity of Tom Massie and Justin Amash in Congress. As George Wallace said, there isn't a dime's worth of difference between the two parties. As for Trump, he is a NY liberal turned populist. He is not rooted in principles but in ego expediency. If he were water he would be a mile wide and an inch deep.

Good post. Interestingly, it is the Democrat party that is going hard-core off-the-rails. Check out this article from The Atlantic (a left leaning publication) titled "The Democratic Party Is Radicalizing". And I believe the reason is because the vast majority of Democrats were 100% sure that Hillary was going to win (because the media reassured them constantly) and now their hate is boiling over.

I'm aware that the "Never-Trump faction" exists, but they are certainly not "growing increasingly louder". Our choice in the 2020 election will be to re-elect our current highly successful president, or to bring in one of the whack jobs vying wear one of Hillary's discarded Kirby vacuum cleaner bags.

Oh "Jenny", that's FUNNY!!!! ROTFLMAO!!! Now i finally know Hillary's wardrobe designer... "Kirby Vacuum Co." HA!

Rick Wilson, David Jolly, and even Charlie Crist back in his Republican days, were excellent, well-meaning, traditionalist Republicans focused on the needs of the general public at large ... especially in Florida. it's a shame there aren't many more of those types of Republicans left. The party is primarily populated now with the incompetent and corrupt TrumpNuts and uber-partisan tribalists.

As Hillary Clinton would say: "The only difference between Republicans and terrorists is that I've never taken money from Republicans".

....just from EVERYONE ELSE, all over the globe...

Think back to those weirdo kids in middle and high school that annoyed the heck out of everyone. Now take a look at Rick Wilson's photo. There you go Rick's that same annoying pathetic looser putz.

Rick Wilson is a pathetic 'never was' except in his own mind He could not get a gig on ANY GOP candidate's campaign in 2016 and there were what 17 He is a bitter old man who defines 'sour grapes' Like all the other never-Trumpers Steve Hayes, Jonah Goldberg, even Bill Kristol apart from appearing on channels with major TDS issues we never hear from them.

If this guy is an "anti-Trumper" he must not be a very good political operative. After all ... Trump is President.


Rick WIlson is spot on.

He certainly is ... as is his very excellent book ... "Whatever Trump Touches Dies". He and Jolly definitely have a very realistic handle on the despicable turn the Republican party has taken in recent years.

But Wilson is not battling Trump here. He is telling the Democrats how to win Puerto Rican votes in this state. This is not about defeating Trump but defeating the GOP in FL.

Not sure how valuable his advice on "defeating the GOP in FL" could possibly be considering that the GOP has had the Governor's office for 20 years and the House & Senate for even longer.

Rick Wilson is a hate monger who capitalizes on the stupidity of others to line his pockets. He's so obsessed with anger and hate, he'd destroy his own party in an attempt to please himself.

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