Dear Gov. DeSantis,
This week, Donald Trump ramped up his attacks on you to the nuclear level. And I’d like to offer some sincere, if unsolicited, warnings.
However, I know that you are averse to taking advice, which may contribute to your high staff turnover. You won your re-election by a wide margin, which may convince you that you have all the answers and that Florida’s response is indicative of the rest of America’s. On top of that, you have flourished by ignoring the mainstream media.
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But is this strategy scalable or tenable in a presidential campaign? I can’t imagine that it will be. These questions remain: (a) can you endure tough questioning from the national press and counter Donald Trump’s punches, (b) can you play road games where you don’t control the venue, and (c) should you win the primary, can you be likable enough to win a general election? The purpose of this open letter is to convince you to prepare for and address these questions right now.
Obviously, your first (and maybe hardest) challenge is to win the Republican primary. One of Trump’s superpowers is to find a person’s weakness and then drag him (or her) down to his level. He achieves this result regardless of whether you (a) allow his attacks to go unanswered, thus allowing him to define your narrative, or (b) fight back and wallow in the mud with him.
So far, you have parried his blows by essentially saying, “I’m too focused on beating the left to engage in attacking a fellow Republican.” But is it possible to defeat Trump without directly confronting him? Can you say you’re just as tough as Trump—while allowing him to say vile things about you? Woodrow Wilson said it was possible to be “too proud to fight.” Well, that strategy wasn’t sustainable for him in the long-run, and it won’t be for you, either.
As a baseball player, you were known for your patience at the plate. It’s smart not to swing at every tempting pitch. But at some point, you have to take a swing. There will come a time when you are in a debate and Donald J. Trump is hurling fastballs, and serving up the chin music. Will you rise to the occasion? That is when we will know if you’re ready for the big leagues.
Granted, we have become somewhat inured to Trump’s tired pitch, which helps explain why his “Ron DeSantimonious” slur has not moved the needle. This particular nickname has the air of truth, but it does not threaten your fundamental brand.
Trump’s recent suggestion that something untoward might have happened between you and some of your former high school students, however, could. One of the memes that Trump sent out on Truth Social this week suggests that you were “grooming” high school girls. While this implication seems wildly unfair, your political team was the first I know of to start loosely lodging the “groomers” slur (and turnabout, as they say, is fair play).
Does Trump’s latest allegation fit into the category of Ted Cruz’s dad being part of the Kennedy assassination, or is there even a hint of something more that might come out later?
Remember, it doesn’t matter that Donald Trump has done everything you will be accused of doing—and worse. Trump’s credibility is not based on him being moral or competent, nor is his utility premised on him avoiding drama.
The problem with casting yourself as “Trump without the baggage” is that the claim disappears the moment your baggage appears. Then the contrast becomes muddied, and your raison d'être collapses. Donald Trump is a master chef of mud pies.
It goes without saying that every serious campaign must conduct “opposition research” on themselves. Lethal information is cause enough for a candidate to sit out a race. But even questionable actions must be disclosed to your team so that they can preempt an attack and/or be prepared to respond quickly. So if there is even a hint of truth to this, have that talk with your wife and top advisors right now.
Assuming that nothing truly damaging from your past exists, you can celebrate the fact that you have now had approximately eight years to observe Donald Trump as a political candidate.
Whereas candidates like Scott Walker, Marco Rubio, Jeb Bush, and Ted Cruz were blindsided by Trump’s unorthodox style, anyone vying for the 2024 nomination has had ample time to study him.
Your goal is to match or “hug” Trump in areas where he is popular with the Republican primary electorate, while simultaneously contrasting him in areas that favor you. This is obviously something you keenly understand. But it doesn’t end there. Winning the presidency will likely require going into the fall of 2023 with a majority of the Trump coalition behind you and the ability to bring home wayward Never Trump conservatives like yours truly.
Nobody said this was going to be easy.
Ultimately, the most important advice I can offer is to take Trump’s attacks seriously and to not assume that your current winning streak (in Florida and the early innings of this nascent presidential race) means you have this game figured out.
In the movie Bull Durham, “Crash” Davis (Kevin Costner) tells his cocky young pitcher, Nuke Laloosh (Tim Robbins), that “You’ve got to play this game with fear and arrogance.” The good news is that you’ve got the second part on lock. And when it comes to the fear factor, I’d settle for a little humility.
