"I’ve looked at life from both sides now
"From win and lose, And still somehow
"It’s life’s illusions I recall
"I really don’t know life at all."
This great classic, "Both Sides Now," was written by Joni Mitchell in 1967 and popularized by Judy Collins, Joan Baez - and maybe others, speaks to the recent political loss we Republicans suffered in a special election for Florida House District 87 last month; an election we couldn't possibly lose, and yet, we did.
House District 87 is President Trump’s home district and is solid Republican.
This posting is my version of "Both Sides Now;" the Republican strategy versus the Democrat strategy. And, yes, this is also my home district.
But, first, a trip down memory lane.
In 2009, then Florida State Senate President Ken Pruitt resigned his seat after the legislative session ended in the spring.
That set up a special election between Republican Joe Negron and Democrat Bill Ramos. I was Republican Party chairman of Palm Beach County at the time (2002-2012).
At the time, I asked Negron, "How can I help?"
Joe told me that the Republican absentee ballots (we now call them vote-by-mail) were not being returned on a timely basis and he needed an absentee ballot paper-chase.
I told him I was on it. I asked that a volunteer group gather together to "chase" Joe's ballots.
How successful were we?
When the election was over, Joe had more votes from absentee ballots and early voting than his opponent had accumulated in the entire race.
In other words, because of these paper-chase efforts, the election was over before people went to them polls that Tuesday.
Fast forward to March 24, 2026. Jon Maples lost to Emily Gregory by around 700 votes.
How did that happen? Sometime between Joe Negron and Jon Maples the GOP ceded the whole concept of vote-by-mail to the Democrats. Everywhere.
In Jon's election, he lost the mail vote by 3000 votes and won at the polls on Tuesday by over 2000 votes. Hence, the 700-vote deficit.
In election campaigns, two strategies exist: the air game and the ground game.
The air game consists of media: television, social media, and postcard mailings.
The air game consists of media: television, social media, and postcard mailings.
The ground game consists mostly of door knocking, signs, and phone calls.
We Republicans got a major dose of the air game.
Literally, every day our (physical) mail box had new large postcards telling us how wonderful Jon Maples is; showing us pictures of his beautiful family, filling us in on his successes in sports, business and politics.
At night, there was Jon on television, reminding us of those same successes.
I never saw a single Emily commercial, although I was told she did some.
I had no idea what she looked like or believed in.
Jon assured us he was for low taxes and that he had the Trump endorsement.
Jon also assured us Emily was for higher taxes.
Jon's campaign cost $500,000 and was run by Tallahassee consultants. Emily’s campaign spent $400,000, virtually none of it on television, large postcards, or large signs.
So, where did Emily’s money go? To texting!
Every day Democrats got texts urging them to get a vote by mail ballot.
"Punch here!" Every. Single. Day.
Subsequently, in the campaign, daily texts said, Vote Early until it was Vote Tuesday.
The ground game strategy of "punch here, get your vote by mail" rattled and overwhelmed the Republican "Here’s Jonny!" air campaign.
The only Vote Tuesday texts the Republicans received were either sent by me or my vender, all personally paid for. The Republican Executive committee?
They simply don't do campaigns against Democrats.
Right now, they’re totally focused on beating an incumbent Republican County Commissioner.
And, how about the Tallahassee angle?
First, in the campaign business, media expenditures generate placement fees back to the consultants who placed the ads.
In other words, television pays. Maybe that mattered and maybe it didn't.
But Emily spent little on television and won.
Jon probably spent six figures on television and lost. Second, when you’re in a state as Red as Florida, too much fighting is intraparty, Republican versus Republican.
Second, when you’re in a state as red as Florida, too much fighting is intraparty, Republican versus Republican.
Before there was Jon Maples, there was Tracy Caruso.
Caruso wanted that seat.
But Tallahassee didn't want Tracy.
Why?
Because she and her husband, Mike, were seen as pro-Ron DeSantis.
Apparently, Tallahassee is MAGA all the way.
Me?
I think President Trump and Gov. DeSantis are two of the best leaders in American history.
I don’t see any need to pick one over the other. I just want to win.
I've looked at elections from both sides now, from a win perspective, the other from a lose perspective.
I've reached one simple conclusion: Those who keep their eyes on the prize will beat those who engage in not-so-friendly fire.
Sid Dinerstein is a former chairman of the Palm Beach County, Florida Republican Party. Read more Sid Dinerstein Insider articles — Click Here Now.
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