After months of getting his ass kicked by Donald Trump and repelling everyone he met, Florida Governor Ron DeSantis finally had a good week(end). Per the New York Times:

For the first time in months, Gov. Ron DeSantis on Saturday showed the aggressive political instincts that his allies have long insisted he would demonstrate in a contest against former President Donald J. Trump.

After headlining two successful political events in Iowa, Mr. DeSantis made an unscheduled stop in Des Moines — a move aimed at highlighting the fact that Mr. Trump had abruptly postponed a planned Saturday evening rally in the area because of reports of possible severe weather.

Congrats to Team DeSantis for accomplishing the absolute bare minimum level of competence. Republicans love their participation trophies. But I digress.

For the last few months, there was rare agreement among political operatives of both parties on two things. One, DeSantis is squandering his best chance to beat Trump. Two, DeSantis’s best bet is to run on an electability message that highlights Trump’s losses in every election since 2015. I have made this argument on Pod Save America in recent months. DeSantis has begun to kinda, sorta tiptoe up to the line of waging this campaign over Trump’s electability. In Iowa and elsewhere, DeSantis touted his big victory in previously purple Florida and decried the “culture of losing” that has infected the GOP in recent years.

However, upon further analysis, the “Trump is a loser” message works better in theory than in practice. It may be DeSantis’s best approach, but it is highly flawed.

Republicans Don’t Believe Trump Lost

How does one run on the platform “Trump is a loser" in the Republican primary when Republican voters don’t think he lost? According to a recent CBS News/YouGov poll, 69% of Republicans do not believe that Joe Biden is the legitimate winner of the 2020 election.

One of the 69% of Republicans who believe the Big Lie — at least according to his public utterances — is Ron DeSantis. The Florida governor has yet to acknowledge that Trump lost in 2020; quite a dilemma when trying to paint Trump as a loser. Politico’s Sally Goldenberg laid out the struggle for DeSantis in a very smart article this week:

Implicit in DeSantis’ argument that he is a more electable alternative to Trump is the idea that Trump actually lost.The fundamental problem for DeSantis — underscored even by blunter messaging from the super PAC supporting him — is that he can’t bring himself to say it.

“First question at first debate: Raise your hand if you think Trump won the 2020 election,” said Republican consultant Alex Conant, who worked on Sen. Marco Rubio’s 2016 presidential race and is unaffiliated in the 2024 campaign. “If a candidate can’t dispose of a fake issue like who won the election, how can voters expect them to handle the real issues?”

The problem for DeSantis? Republican voters do not want to hear the obvious truth that Trump lost the election fair and square. In that CBS News/YouGov poll, six in ten Republicans prefer a candidate who says Trump won in 2020.

Republicans — like all primary voters — are looking for a winner. They think Trump is a winner because no one will tell them otherwise.

Winner’s Don’t Lose to Losers

When looking at highly engaged primary voters, it’s very difficult to tell whether the polls drive the narrative or vice versa. While this could change, the narrative for the last couple of months indicates that Donald Trump is kicking Ron DeSantis’s ass. Despite an indictment, a verdict holding him liable for sexual assault, and a morass of legal trouble across the country, Donald Trump has risen in the polls, and Ron DeSantis has sunk like a stone.

DeSantis looks hapless and weak, while Trump looks ascendant. In other words, Trump equals winner, and DeSantis equals loser. In the most recent Morning Consult tracking poll, Trump leads Ron DeSantis 61% to 18%. This particular poll is a bit more Trump-friendly than some of the others. However, the FiveThirtyEight polling average has Trump leading DeSantis by a margin of 49% to 26%.

It’s hard to call yourself a winner and the other guy a loser when the “loser” is beating you by a large margin.

The Proof is Not in the Pudding (Fingers)

Those arguing for electability as the best anti-Trump message for a non-Trump Republican often cite President Biden’s successful strategy in the 2020 election. In that race, the early energy and enthusiasm was behind progressive stalwarts Bernie Sanders and Elizabeth Warren, and fresh faces like Pete Buttigieg. Biden held a lead nationally but trailed — and eventually lost the nominating contests in states like Iowa, New Hampshire and Nevada. The polls also showed that voters’ top priority in selecting a nominee was not their policy agenda or personal characteristics. It was their ability to beat Trump. Most of all, Democrats wanted to win.

Biden’s campaign smartly made electability the centerpiece of the campaign. But Biden had an advantage DeSantis does not. During the 2020 Democratic primary, his polling consistently performed better against Trump than the rest of his rivals. Early hypothetical polling is a massively flawed instrument with a predictive power that barely exceeds dart throwing, but it’s the only available data point.

DeSantis’s electability argument does not show that he is inherently a more likely winner than Trump in a race against Biden.

It is still early. There are a lot of legal shoes to drop that could alter the political landscape, but running against Trump as a loser is easier in conception than execution.

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