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Trump: Playing Not to Lose

The opinions expressed by columnists are their own and do not necessarily represent the views of
AP Photo/Charles Krupa

Candidate Trump circa 2016 was aggressive and played to win. Former President Trump of 2023 is playing not to lose, all but guaranteeing his loss either in a primary with Ron DeSantis or in the general election against Joe Biden.


Playing to win and playing not to lose sound like the same thing, only slightly rearranged. But, in reality, they are as different as day and night. Have you ever seen a football team grab a big lead early, say 24-0? And then they went on to lose 28-27 on the last play of the game. How? In many cases, the play-calling that got them the big lead was aggressive. Taking risks—going for it on 4th down, passing in an obvious running situation, putting in some trick plays—paid off and led to a befuddled defense and a lot of early points. At half-time, the coach says that now they just need to run out the clock. So they run and punt. They make short passes that don’t move them down the field. And in the meantime, their opponent starts putting points on the board until the game is lost. One sees such failures in sports but also in politics.

Coming down that Trump Tower escalator in 2015, Trump exuded confidence and put his finger on the issues that meant a great deal to a large number of Americans: out-of-control immigration, jobs lost to China, a loss of hope, a weakened U.S. position in world affairs, and poor economic performance. Candidate Trump put forth his solutions in bold strokes and took on 16 of the GOP’s best and brightest, including hotshot young governors, such as Walker,  Cruz and Jindal. And he beat them all. He crushed them. I remember him teasing Jeb Bush on how the latter kept moving further away from the center of the debate stage, as Jeb’s poll numbers kept going down. That was Donald Trump going for the win. He went on to defeat Hillary Clinton and usher in four years of economic growth (pre-Covid), renewed American pride, a stronger military, and a leading role for America in the world.


Let’s fast-forward to today. Donald Trump has said that he may not partake in the GOP primary debates. He seems terrified of Ron DeSantis, making up stupid names for him, telling him that he owes his career to the former president, or complaining that Florida is a lousy state. Candidate Trump did not seem to fear anyone; former President Trump seems terrified of a younger, more aggressive version of his former self, one who is disciplined and popular in the party. Trump’s demand that DeSantis stand down sounds eerily similar to Hillary’s claim that it was her turn, which led to the decimation of the candidates who dared to run against her. While she did win primaries (remember those Democratic “super delegates” coming to the rescue?), she lost to Donald Trump in one of the most stunning presidential outcomes in U.S. history. Is Donald Trump setting himself up for a similar fall against the almost-not-there Joe Biden?

The 2016 version of Donald Trump would have all but invited Ron DeSantis to run against him. You think you can beat me? I will show you that I will crush you. But today, he seems scared, even praising the destroyer of California, Gavin Newsom, before giving any praise to Governor DeSantis. Several of his personally-chosen candidates in 2022 lost winnable races; they were chosen because they were personal friends or because they said what Trump wanted to hear about the election being stolen in 2020. Apprentice-era Trump would put his understudies through their paces until the top performer emerged. 2022 Trump chose those who fawned the most over him and thus brought in weaker candidates who lost in favorable states like Georgia and Arizona or against horrific candidates, as in Pennsylvania. Trump has never taken responsibility for his hand-picked candidates who lost. Not taking responsibility for one’s actions is the hallmark of a loser. Look at Joe Biden blaming the chaotic exit from Afghanistan on Donald Trump. A winner takes responsibility for his failures; that’s the only way he can get better.


None of the non-DeSantis Republican candidates seems like much of a threat to Donald Trump. Some seem to be auditioning for a VP slot. If Donald Trump can jawbone Ron DeSantis out of the primary, then the former president will not have the disciplined challenge he needs in order to make him into a first-rate candidate for November of 2024. Americans are not stupid—they see the border, they feel the economy, and they realize that America is losing its place in the world to China, and even with all that, they do not run to vote for Republicans in large numbers. The Democrats have the voting ground game—early voting, vote harvesting, vote curating, etc. The Republicans have the issues, especially with such an unpopular duo of Biden and Harris. Still, Biden is probably the favorite against former president Trump for two reasons. There are many people who hate Trump at such a visceral level that they will even vote against a better economy, a closed border and cheaper gas so as not to vote for Trump. But also, an undisciplined Trump will find his way to alienate those independents who do not like the state of America today and would have been open to voting for Trump. Donald Trump either needs a solid DeSantis primary challenge to make him a far more disciplined candidate or he needs to go back to the play-to-win Trump of 2016 and stop fearing his competition or glossing over GOP debates. The current version of Donald Trump is playing not to lose, all but guaranteeing that he will lose either to DeSantis or to Biden, however unpopular, corrupt and unsuccessful the current president is.


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