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The top Trump regrets of 2019

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The biggest moments of 2019 that Donald Trump regrets, and what he might do differently in the future, in his own words.

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2019 was a turbulent year in American Politics, with many moments and missteps the American president Donald Trump regrets.

Because America has never had a shorter attention span, it’s sometimes helpful to look back at reflective moments where the American President expressed regret.

Some of the topics Trump regrets are personal, and other statements can shave billions off the global markets. Because it’s Trump, anything goes. So here is our short roundup big regrets from Donald Trump, in his own words.

1. Trump really wishes he didn’t appoint Jeff Sessions as attorney general.

Jeff Sessions shakes President Donald Trump's hand the day he is named Attorney General.
Jeff Sessions shakes President Donald Trump’s hand the day he is named Attorney General.

In a candid June 2019 Meet The Press interview with NBC’s Chuck Todd, Trump admits he regretted appointing Jeff Sessions as Attorney General.

Todd asked Trump “If you could have one do over as president, what would it be?” Trump replied that he wanted a do over regarding “personnel.”

“I would say if I had one do over, it would be, I would not have appointed Jeff Sessions to be attorney general.”

Donald Trump

Todd asked if appointing Sessions was Trump’s “worst mistake,” to which Trump replied “yeah, that was the biggest mistake.”

Fortunately for Trump, he was able to appoint a new Attorney General, so hopefully the regrets are fewer.

2. Trump regrets not raising tariffs on China sooner.

Donald Trump shakes hands with Xi Jinping at 2019's G20 in Osaka.
Donald Trump shakes hands with Xi Jinping at 2019’s G20 in Osaka.

Surrounding late Summer’s G7 summit, media sites frenzied over Trump’s comments on trade policy. Specifically a misunderstood quip where Trump said he had “second thoughts” on his tariff policy toward China.

Many media outlets mischaracterized these comments as a back down. White House spokeswoman Stephanie Grisham issued a clarifying statement:

“The president was asked if he had ‘any second thought on escalating the trade war with China’. His answer has been greatly misinterpreted. President Trump responded in the affirmative – because he regrets not raising the tariffs higher.”

Stephanie Gisham, White House spokeswoman

Because the trade war with China is ongoing, we can assume Trump will learn to apply more pressure in the future.

3. Trump wished he didn’t sign the Whistleblower Protection Act

In 2017, President Trump signed the Veterans Affairs Office of Accountability and Whistleblower Protection. This law safeguards Department of Veterans Affairs employees that report wrongdoing. The law only applied to employees of the Department of Veterans Affairs.

Legal review site Law & Crime wrote a cranky think piece about one Trump tweet from November 2019. The tweet implied that Trump regretted signing whistleblower legislation. This is timely and relevant in the wake of impeachment hearings:

Law & Crime’s journalist Jerry Lambe wrote that “the whistleblower protection bill Trump signed” has “nothing to do” with the now infamous Ukraine call whistleblower.

However, Lambe appears to miss the part of real world politics where perception matters more than prose. For example, the “Patriot Act” is branded to feel patriotic. The “Whistleblower Protection Act” — however inapplicable in law — is a brand Trump can leverage. This act can highlight Trump’s willingness to protect freedom of information, even if his tweet regarding Ukraine are outside the law’s scope.

Just because the Whistleblower Protection Act doesn’t apply to Ukraine, doesn’t mean Trump can’t tweet his regrets.

4. Trump lamented ‘pressure’ he put on his brother who died of alcoholism.

A portrait of Fred Trump Jr. displayed in the Oval Office.

Fred Trump Jr. felt pressure to take over the Trump family business because he was the oldest son. However, life took a different course and Fred fell into in alcoholism and chaos leading to an early death in the ’80s.

“I do regret having put pressure on him,” Trump shared this year. Taking ownership of the family business “was just something he was never going to want. It was just not his thing. . . . I think the mistake that we made was we assumed that everybody would like it. That would be the biggest mistake. . . . There was sort of a double pressure put on him”

Trump felt that both his father and himself pressured Fred Trump Jr., who died in the ’80s due to alcohol-related illness.

5. Trump only regrets “some” retweets, but stands by all his original tweets.

Donald Trump sat with Steve Scully, C-SPAN’s Political Editor, who asked in a televised interview whether or not Trump regretted any of his tweets. Because it’s Trump, he took the opportunity to humble brag.

Trump proudly suggested he stands by his own tweets because he’s often right. He used the famous tweet accusing Obama of wiretapping the Trump campaign as proof of vindication.

He did, however, suggest that some of his retweets can cause trouble.

In summary, Trump regrets a few moments, and shared deeply personal regrets.

So throughout 2019, where his successes — against all odds — have never been more abundant, it is worthwhile to see his personal reflections as a leader, brother, and negotiator.

We can assume Trump will keep sharing moments like these, because he can often be quite candid.

We hope to learn more of Trump’s private thoughts regarding impeachment. Whether or not he regretted losing Omarosa, Bolton, or other high-profile staff. And hopefully, we learn whether or not Trump regrets that now infamous call with Ukraine’s leadership.

So we look forward to 2020. And assume just because this year was great, perhaps next year can be better. There’s plenty more political theater to come in the election year ahead!

Brett MacDonald

Brett MacDonald

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