Did Ron DeSantis just make a huge mistake? A couple of lessons from Teddy Roosevelt in that regard…

The Florida Governor officially enters a Republican field completely dominated by President Donald Trump, putting himself in the spotlight while remaining at the mercy of events, left to hope some outside force fells the former President because there is nothing he can say or do to change the dynamic.

I was wrong:  I always figured Florida Governor Ron DeSantis wouldn’t formally enter the 2024 Republican Presidential Primary if former President Donald Trump continued to be a juggernaut, leading the field by a stunning 34 points in the latest Real Clear Politics average.  In my view, it made no sense to risk his well-earned reputation by running into the Trump buzzsaw and he was far better off biding his time until 2028, especially as he would likely be a shoe-in for the Vice President slot on a Trump ticket.  Governor DeSantis, however, threw caution to the wind as they say and formally launched his campaign on Twitter Spaces earlier this week.  The best I can say:  He can only hope the actual campaign is smoother than the launch, which was notoriously plagued with issues making headlines throughout the mainstream media, or the entire campaign will be defined by the decision to use Twitter in this unusual fashion.  Sadly, it seems to me that Governor DeSantis has made a tremendous, potentially fatal, mistake at this stage.  Time will tell if he ultimately prevails in the primary, but whatever happens, he has put himself in a position a savvy politician does everything possible to avoid.  The governor, by entering at this point in the race, is no longer in control of his own fate.  By that, I mean there is nothing he can personally do, entirely on his own, to stop the train for President Trump.  Some, of course, may disagree with that assessment, but the fact remains the former President is running up primary numbers close to the equivalent of an incumbent President.  This is after he’s been impeached twice, indicted at least once, and found guilty of sexual assault in a civil case along with literally thousands of other mini-scandals and controversial statements.  Republican primary voters know this.  The general electorate knows this, and yet he’s still beating President Biden by a larger margin than the Florida governor right now.

At least in my opinion, there is nothing Governor DeSantis can personally say or do to change that dynamic.  There is no statement he can make on the debate stage, no policy he can propose, no speech he can deliver, no dirt he can dig up, no advertisement he can run on his own to alter the state of the race enough to propel him to victory.  Rather, he must hope that President Trump falters somehow, either through something colossal misstep of his own on a scale unlike any of his previous debacles or some indictment, conviction, or other legal challenge that fundamentally alters the reality of the race.  If you don’t believe me, ask yourself what Governor DeSantis could possibly say or do to take down a man who has survived accusations of being a traitor, a white supremacist, a wannabe dictator, a maniac, a fool, a rapist, a thief, a corrupt businessman and politician, and more?  Do you truly believe some snappy comeback at a debate or slick policy proposal is going to upend all of that?  If you can think of something, please feel free to share it in the comments because I’ve certainly tried and have come up with nothing.  This leaves Governor DeSantis at the mercy of events, hoping the great kaleidoscope of politics, as Teddy Roosevelt liked to refer to it, changes between now and when the voting begins.  In other words, the governor can be a political genius the likes of which the world has never seen, and he will still lose – or worse, more on that in a moment.

Teddy Roosevelt himself is an illustrative example of the limits of political genius.  He is widely heralded as the most gifted politician of his era and many another besides, having secured the largest popular vote victory in US history in 1904.  Throughout his career, he possessed the uncanny ability to capitalize on events and propel himself to the center of the action as the kaleidoscope shifted around him.  Roosevelt was, however, in the political wilderness for more than a decade before his moment finally arrived in 1898 and the moment came beyond any control of his own. A year earlier, he was merely Assistant Secretary of the Navy, a powerful post, but one he was relegated to for being considered too maverick and wild for even his own party.  The last election he won was for the relatively minor rank of New York State Assemblyman back in 1884, when he angered the party machine by aggressively pursuing what he considered the corrupt influence of money in politics.  He suffered a devastating loss running for mayor of New York City in 1886, taking third place and winning a measly 27% of the vote.  In the aftermath, he was relegated to the role of an unelected bureaucrat both as Civil Service Commissioner in Washington DC and Police Commissioner in New York, where he further angered party members by aggressively pursuing corruption at all times.  At that point, he had no plans to run for elected office ever again, and believed he would spend the rest of his career as a writer until he found himself back in Washington as Assistant Secretary of the Navy in 1897.  He achieved this post only because of a close relationship with a powerful Senator, Henry Cabot Lodge from Massachusetts, and most of his fellow Republicans kept their distance from him until war with Spain broke out.  The war would transform him from a thorn in the side of the establishment into a national hero and political superstar in six months.  After almost single handedly winning the Battle of San Juan Hill and acting with enough bravery for several lifetimes, Roosevelt returned victorious from Cuba in August 1898.  He was elected governor of New York by a landslide that November.  Two years later, he was Vice President on the Republican ticket and less than a year after that he was President when William McKinley was assassinated.

The lesson:  There are thousands of alternative realities where Roosevelt, a man carved into the face of Mount Rushmore, was never President.  No war with Spain, and he has no means to unite the party behind him.  No decisive victory at San Juan Hill and no national hero status, forget surviving under brutal conditions that cost him about 20% of his unit.  No McKinley assassination and very likely no Presidency because Roosevelt wasn’t suited to the second slot and hated the role.  Given his passionate nature, it seemed only a matter of time before he royally upset the party beyond repair.  In other words, when the time came, he capitalized on it with the utmost political skill, but he was not in control of whether those times actually came.  We see this in his career post-Presidency as well.  Roosevelt left office the most famous man in the world and the most influential figure in public life, but his successor William Howard Taft simply wasn’t up to the job, being far more suited to either the Supreme Court or the golf course.  Though the two were close when Taft served as Roosevelt’s Vice President, a rift developed between them and Roosevelt found himself back in another primary contest in 1912.  The Republican Party, however, feared he had become too progressive since leaving office and while they believed he could win the Presidency, chose Taft instead.  Roosevelt responded by starting the Progressive Party, colloquially known as the Bull Moose, and running on a third party ticket.  He achieved the most successful outing for a third party candidate in history, but Democrat Woodrow Wilson won the election in a landslide, leaving Roosevelt in a political wilderness deeper than any he had ever known.  He was ignored as a crackpot, a crank, and a warmonger throughout the entire lead up to World War I and well into the early days of the war as he harangued Wilson for his neutrality policy and lack of preparedness.  It was only after Germany continued using submarines to sink vessels with US citizens aboard that Wilson in particular and America at large realized Teddy had been right all along, and suddenly he was thrust into the spotlight yet again.

Governor DeSantis has demonstrated that he is an adroit politician with serious managerial skills, but I think everyone, even his most ardent supporters, agree he is no Teddy Roosevelt, lacking the raw charisma and personal dexterity, and yet he finds himself as much a victim of events as the legendary leader ever was.  Perhaps even worse, entering the primary at this stage is not without serious, serious risk, one which is rarely discussed or mentioned by his supporters.  The Florida Governor doesn’t have the luxury of running a low profile campaign while building a national organization for a future bid.  Instead, he finds himself immediately at the center of events, where he will be a primary target for both President Trump and the media.  Some conservatives, largely Trump supporters, are already grumbling that Governor DeSantis only announced because of pressure from his donors and, perhaps needless to say, those donors are primarily the GOP establishment that loathes President Trump and by extension the base of the Republican Party.  The former President himself will certainly amplify this idea, rightly or wrongly, and if he can depict Governor DeSantis as an establishment stooge, his political career will be completely over.  There are no shortage of other ways this doesn’t end well, either.  A lackluster performance could doom him to the dustbin of other governors that simply couldn’t translate their appeal to a national level like Scott Walker.  A catastrophic debate performance or other stumble could easily wound him permanently like Rick Perry.  The media will surely be waiting to pounce, as will President Trump, leaving me to wonder at least why he didn’t just wait and see and ultimately take the VP slot.  Putting this another way, the Governor’s two greatest assets are his not being Trump and simultaneously having a high profile in the Republican party.  If the party prefers Trump, there is nothing the Governor can do.  If, however, it seems like they prefer another candidate, Governor DeSantis can get in the race as late as next fall and still win.  Why he would get in now remains a mystery, at least to this observer.

Please note:  None of this should be construed as anti Governor DeSantis.  I have made no secret that President Trump is my first choice, but I have the utmost respect for the Florida Governor and wish him the very best.  This is only to say that his announcement this week seems like a riskier move than he need have made under the circumstances, one I hope does not prove fatal to his future political career.


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