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Character Judgement Has Always Been Trump’s Achilles Heel

We wish we didn’t have to say this, but former President Donald Trump’s biggest problem as President, and in his 2020 campaign, and in his post-presidency, has always been the people with whom he surrounded himself.

In the aftermath of his unlikely victory in 2016 Trump was clueless about how to staff his administration, and, as Steve Bannon admitted, he made what was in essence a deal with the devil – the Republican establishment – to fill his administration with people who not only didn’t support him, but who were actively opposed to his America First agenda.


And this problem was not found only in the obscure reaches of the federal government – it was right in the White House and included his daughter Ivanka and son-in-law Jared Kushner, who were two of the greatest impediments to the MAGA agenda.


That’s not to say every Trump hire was no good – Mark Meadows, Mercedes Schlapp, Marty Dannenfelser and many others on Trump’s White House staff, and throughout the Administration, were solid conservatives, but the handful of America First loyalists were hardly enough to ride herd on the entire federal government, and the anti-Trump Capitol Hill GOP leadership, which was bent on thwarting Trump’s agenda.


Trump’s 2020 campaign team, while not disloyal in the same way some of his administration hires were, was easily the most advice-resistant help-proof campaign I’ve dealt with in almost 50-years of politics. They were warned well in advance of the election what Zuckerberg was up to with the drop boxes and the grants to local election officials to run turnout operations in Democrat-heavy areas in swing states, including a warning letter signed by over 500 conservative activists organized by ConservativeHQ, and they ignored it.


So, the unforced error Trump made in inviting Kanye West and Nick Fuentes to dinner in the midst of the row over Kanye’s anti-Semitic comments did not surprise us in the least, because it fits a pattern – not of Trump being an anti-Semite, because he’s not, it fits the pattern of Trump associating with people who do not have his best interests and political agenda as the basis for the association.


And instead of taking the opportunity to publicly tell Kanye West he was wrong to make the anti-Semitic remarks he made, something the former President could well have done based on his long support for Israel and business associations with some of America’s most prominent Jewish real estate investors and developers, he instead chose to appear to make excuses for West’s tirades by speculating he was mentally ill – “a seriously troubled man” – instead of a man in need of serious correction and the education necessary to amend his views.


For his part, after getting what amounted to a pass on his reprehensible behavior West claimed Trump screamed at him during the dinner over the rapper's ambitions to run for president in 2024, thereby making Trump look small and neutralizing any benefit Trump may have thought he was getting in the Black community from an association with “Ye.”


Or, maybe the case is that Mr. Trump, having risen to the presidency on the strength of his celebrity status as a television and pop culture star assumes other celebrities have something to say worth hearing and are as politically astute as he is, which would be another failure in character judgement.


Whatever the case, why give your enemies more ammunition to use against you?


Mr. Trump, for all that we like about him, is unfortunately beginning to remind us of a tragic figure from antiquity, as the Greek tragedian Sophocles wrote in his play Antigone:


No man can be fully known, in soul and spirit and mind, until he hath been seen versed in rule and law-giving. For if any, being supreme guide of the State, cleaves not to the best counsels, but, through some fear, keeps his lips locked, I hold, and have ever held, him most base; and if any makes a friend of more account than his fatherland, that man hath no place in my regard. For I – be Zeus my witness, who sees all things always – would not be silent if I saw ruin, instead of safety, coming to the citizens; nor would I ever deem the country's foe a friend to myself; remembering this, that our country is the ship that bears us safe, and that only while she prospers in our voyage can we make true friends.


Donald Trump remains the leading contender for the Republican nomination for President, and the greatest and most effective spokesman for the Make America Great Again agenda, but we often despair that the people with whom he surrounds himself will be his undoing.



  • Trump administration personnel

  • Republican establishment

  • Trump hires

  • America First agenda

  • Ivanka Trump

  • Jared Kushner

  • Mark Zuckerberg

  • mail-in voting drop boxes

  • Kanye West

  • Nick Fuentes dinner

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