“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 classic song by Joni Mitchell (1967), popularized by Judy Collins and Joan Baez, speaks to the recent political loss Republicans suffered in a special election for Florida House District 87 last month—a race we couldn’t possibly lose, yet lost.
House District 87 is President Trump’s home district and has historically been solid Republican. This post is my take on “Both Sides Now,” examining Republican versus Democratic campaign strategies—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 after the legislative session ended in spring. That set up a special election between Republican Joe Negron and Democrat Bill Ramos. At the time, I was Chairman of the Palm Beach County Republican Party (2002–2012).
I asked Joe: “How can I help?” He told me that Republican absentee ballots weren’t being returned on time and he needed a paper chase. I said I was on it—I organized volunteers to “chase” his ballots. By election night, Joe had more votes from absentee ballots and early voting than his opponent had accumulated in the entire race. In other words, these efforts decided the contest before voters even went to polls that Tuesday.
Fast forward to March 24, 2026: Jon Maples lost to Emily Gregory by about 700 votes. How did this happen? Sometime between Joe Negron and Jon Maples, the GOP completely ceded the concept of vote-by-mail to Democrats everywhere.
In Jon’s election, he lost the mail vote by 3,000 votes but won at the polls on Tuesday by over 2,000 votes—resulting in a 700-vote deficit.
In election campaigns, two strategies exist: the air game and the ground game. The air game involves media: television, social media, and postcard mailings. The ground game consists of door knocking, signs, and phone calls.
We Republicans got a heavy dose of the air game. Every day, our mailboxes received large postcards praising Jon Maples—showing pictures of his family and detailing his successes in sports, business, and politics. At night, Jon appeared on television, reminding us of those achievements. I never saw a single Emily commercial—though I was told she had some.
Jon assured us he supported low taxes and had the Trump endorsement. He also claimed Emily favored higher taxes. Jon’s campaign cost $500,000 and was run by Tallahassee consultants. Emily’s campaign spent $400,000, with virtually none on television, large postcards, or signs.
So where did Emily’s money go? To texting. Every day, Democrats sent texts urging voters to request a vote-by-mail ballot. During the campaign, daily texts urged “Vote Early” until it became “Vote Tuesday.” The ground game strategy—“punch here and get your vote by mail”—rattled and overwhelmed the Republican air campaign’s “Here’s Jonny!” approach.
The only Vote Tuesday texts Republicans received were from me or my vendor—all personally paid for. The Republican Executive Committee? They simply don’t run campaigns against Democrats. Right now, they’re focused on beating an incumbent Republican County Commissioner.
And how about Tallahassee? First, in campaign spending: media expenditures generate placement fees that go back to the consultants who placed ads. In other words, television pays—though it’s unclear if that mattered. But Emily spent little on television and won. Jon likely spent six figures on television and lost. Second, Florida is a red state where too much intraparty fighting occurs between Republicans. Before Jon Maples, there was Tracy Caruso—but Tallahassee didn’t want her. Why? Because she and her husband, Mike, were seen as pro-Ron DeSantis.
Apparently, Tallahassee is MAGA all the way. I think President Trump and Governor 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: the win perspective and the 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.
