10 Reasons Donald Trump isn’t the Greatest President in History

A lot of people scoff at the idea that Donald Trump just missed being the greatest man ever to hold office. However, open-minded folks with a sense of history, a basic understanding of American politics, and an idea of who Donald Trump is in relation to American values will understand. 

Trump the Icon

Donald Trump smirking and pointing toward the crowd after a rally, PA 2016.
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People forget that long before Trump became a political figure, he was a businessman, a playboy, and a poster boy of American elitism.  He seemingly had it all. Even when he failed, his empire and brand had grown so huge that banks bailed him out time and time again because they had so much invested in his persona.

The Modern John Wayne 

American rancher standing outside in cowboy gear watching his herd to represent rugged individualism.
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America has always loved the concept of John Wayne. A man’s man who would step into a fight to protect a lady or save the day from thieves trying to steal a working man’s ranch. Even before  The Apprentice, Trump had forged a reputation as a tough, lumbering Oaf of a man who seemed to do things his way whether you liked it or not. His reputation was that of a tough guy who you could count on when the chips were down.

Hollywood Loved Him 

celebrity signing autographs for a group of ecstatic fans.
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It’s easy to forget that Trump was once, and I suspect, still a hard-core Democrat that Hollywood adored. His Cameo in Home Alone 2 brought applause to theatergoers everywhere, and Sex in the City mentioned the man on numerous occasions.

He Was Accessible 

Trump supporters hold up a "Make America Great Again" sign at a 2018 rally.
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Even yours truly had a chance encounter with the man years ago when we both attended a retirement celebration for the CEO of a Chicago news outlet long before his ambitions turned towards politics. Everyone knew Donald Trump, and anyone could buy a ticket to the numerous seminars and events he attended nationwide.

The Boss

Donald Trump speaks to a crowd during his 2016 presidential campaign.
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The Apprentice sealed Donald Trump’s place in history as a no-nonsense businessman who would reward talent and unabashedly dismiss slackers with his famous “You’re Fired” retort to a failed contestant. The show was wildly popular and, in a way, personified the idea that the American dream was indeed based on hard work and perseverance.  What fans of the show did not understand was that the show was entertainment and not steeped in reality.

Winning the Election 

President Trump waves to the crowd after winning the Indiana Primary in 2016.
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Written accounts of Trump’s reaction to winning the 2016 election over Hillary Clinton are fairly consistent and can best be described anecdotally as “Shock and Awe.” Although Trump wanted to win, he had little reason to believe he would succeed against the mighty Clinton machine. What he underestimated was the public’s distrust and dislike of the Clintons.

10 Failures That Doomed His Presidency

Donald Trump giving a speech with the American flag as a backdrop.
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It’s incredible to me how many media and political pundits dismiss Donald Trump as ignorant, stupid, or clueless as to the way government should be run.  He’s not stupid; he’s stubborn, and although that stubbornness may be successful in business, his unwillingness to compromise has been his Achilles’ heel in government. 

While it’s true that Trump’s historical knowledge of government and political norms isn’t exactly stellar, his knowledge of people and the electorate is genius. Had he accepted the idea of compromise while explaining his decisions to the public, his popularity would have crossed political lines and soared out of the gate.

Moving to the Middle 

a handshake
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One of Trump’s many character flaws is that he believes his instinct to be unassailable. Like an addicted horse player, he bets the favorite constantly, not realizing that favorites only win 30% of the time. He believed the hard-core Republican base was his winning ticket and had to be placated, nurtured, and enraged for his Presidency to succeed and guarantee reelection to office. 

Had he moved to the political center and accepted or acknowledged a willingness to work across the aisle on some democratic initiatives, he would have drawn independents and some moderate democrats to his side.

The Best and the Brightest 

Former New York Mayor Rudy Giuliani at a parade in 2022.
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The irony of Trump is that his television show proclaimed to be searching for the most qualified, driven candidates possible to serve as managers and project developers for Trump’s companies. As President, however, he scraped the bottom of the barrel when choosing advisers and cabinet members to help him lead the country. 

Rudy Giuliani, Steven Miller, Steven Mnuchin, and Ben Carson should never have been allowed access to the White House, much less be involved in decision-making at the highest levels of government. Trump’s unwillingness to be challenged by those with higher intellect was a major detriment to his Presidency.

Needless Personal Wars 

The late senator John McCain speaking at a ralley in 2010.
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Trump’s well-known personal attacks on individuals’ characters and ethics helped him win the election, but continuing to bully and demean people as President was beneath the office of President and drove would-be supporters away. Attacking the likes of Stacy Abrams, Ruth Bader Ginsburg, Glenn Beck, and the deceased John McCain made Trump look weak and childish.

The Russians 

Belgrade, Serbia - January 17, 2019 : Vladimir Putin, the President Russia attending press conference.
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It’s not a far stretch to believe Vladimir Putin ordered the invasion of Ukraine in part because President Trump legitimized and supported the Russian President’s authoritarian behavior. In fact, Trump’s passive approach to Russian aggression legitimized a Russian agenda that included assassination and imprisonment of political adversaries.  

Trump should have railed against the Russian interference in the presidential election and condemned and sanctioned the country for that interference. If the Russians helped him win the 2016 election, they helped him lose the 2020 contest as well. Trump would have won if he kept a firm and decisive policy sanctioning Russian aggression.

The Supreme Court 

The United States Supreme Court building in Washington DC.
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The biggest mistake of his Presidency is one in which he fell in line with the hard right republican wing of his party and packed the court with fiercely conservative judges. He thought his base would re-elect him on this act alone. He failed to recognize the damage such a court would cause with lockstep voting on issues such as gun control and abortion rights for women.  Although these issues weren’t on the docket during his presidency, a more neutral court would have been hailed as a triumph by a reasoned President. 

The Impeachments 

Dome of the US Capital Building with the flag waving in front.
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There is reason to believe that Trump’s admonishment and condemnation of Russian involvement and some cooperation with Democrats on the issue would have stopped the first impeachment in its tracks. He was fortunate that Republicans were in control at the time, or he would have probably been removed from office. Again, much of his problems were self-inflicted by horrible advice and a sense of self-grandiosity.

Race 

The US-Mexian border in Arizona.
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We can call Donald Trump a lot of things, but he’s not a racist. He may call someone a horrible name or ridicule a poor country, but there is no evidence that he hates folks for the color of their skin. One of the reasons he came so close to beating Biden in 2020 was the support he received from minorities, including Latinos who, by and large, hate America’s unstable border policy.  

Trump received over 30% of the Latino vote. Had he made an effort to court both African-American and Latino voters, he may have shaved off enough support to get the win. 

His Kids

Donald Trump and his daughter Ivanka in 2014.
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 Children of elected officials have no place in government. Trump’s children, especially Ivanka, her husband Jared Kushner, Don Jr., and  Eric, are not qualified to be advisers to the office of President. Sweetheart deals and favoritism doom many politicians and, at best, are major distractions, like President Biden is experiencing with his son Hunter. 

Jared Kushner’s sweetheart deal with Saudi Arabia for 2 billion dollars is proof enough that kids and their spouses are bad news. A better choice would have been to exclude them from the political realities of governing and show the world that nepotism would never be an issue in the Trump White House.

Mitch McConnell 

Kentucky senator Mitch McConnell.
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To say the relationship between McConnell and Trump was terse would be putting it mildly. These two hate each other with a passion, and McConnell’s refusal to pump more personal stimulus into the American economy during the onset of COVID-19 doomed Trump’s reelection bid. If Trump had nurtured even a tepid relationship with Nancy Pelosi, he could have passed the same legislation Biden did after the election and been hailed as a savior.

January 6th 

An angry protestor shouting on Jan 6, 2021 at the protest in Washington DC.
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At the present time, Trump is the leading candidate to win the Republican primaries and become the party’s nominee. While Republicans may hail this as a victory that will put Trump back in the White House, it is most assuredly not. Trump has amassed over 90 criminal indictments that many Republicans believe are politically manufactured. The truth, however, is that these indictments are severe and won’t go away. 

Trump lost his reason and his ability to think straight when he lost the 2020 election, which frankly, he should have won.  But he didn’t and he lost fair and square.   His behavior after the election bordered on rabid, and commercials and political ads will play non-stop showing an insurrection and assault on the nation’s capital that even hard-core Republicans have trouble dismissing.   The shame is that he could have been great. The reality is that he fired himself.

11 Reasons To Re-Elect Biden

Then candidate Joe Biden gives a speech on the campaign trail in 2020.
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Trump’s failures make Joe Biden the obvious choice. Here are 11 reasons to re-elect the incumbent in 2024. 

The Terrifying Agenda Should Trump Win

The US Constitution rolled up with the "we the People" showing at the top. It's resting on an American flag.
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Here’s a brief summary of Project 2025 highlighting why it’s so dangerous and goes against everything America stands for.