Defeating Trump – Really?

[This is the second of a two-part musing about the 2020 American presidential election.  Today, a longer piece on “Who will win the Democratic nomination?”]

If we assume that Trump can in fact be defeated, the next question is whether the Democrats will nominate a candidate who can achieve that goal.  The answer is not really obvious.

Having now seen the results in Iowa and New Hampshire, two of the least representative states in the U.S.A., and having seen the candidates participate in the bloodbath Wednesday night that they claimed was a debate, there are seven people left with a legitimate shot at the Democratic nomination.   They are none of them perfect, and none of them are remotely saviours, but of course all of them are better than Donald Trump. 

(That doesn’t mean they can beat him.  Lots of people are better than Donald Trump.  Lots.)

Let’s look at the survivors.

Joe Biden

Start with the early front-runner, Joe Biden.  Joe is a spring chicken, at only 78 years old, and he has the advantage that the electorate already found him suitable for the presidency by electing him Vice President in 2008 and 2012 (just ask him).

Joe has three problems. 

First, he was never the smartest guy in the room.  He’s not stupid, but he’s more of a relationship person, not a rocket scientist.  Beside some of the other candidates, he can look pretty pedestrian.  Now, Donald Trump looked pretty stupid beside some of his rivals, and look what happened.  Still…

Second, Joe appears to have only one message:  “I’m the only one here who’s done any of this stuff.”  While that is true to a certain extent, that message is now getting old.  Against Donald Trump, it won’t cut it.  Trump has been President.  A bad one, to be sure, but Biden doesn’t have an experience advantage.  So, what else can he offer against Trump?  Policy proposals?  Not really. 

Third, and sadly, Joe appears to have lost a step.  Not everyone can get to the age of 78 and still be 100% as vigorous and on point as they once were.  Even in the Wednesday debate, when he was at his best, he was still a step behind everyone else on the stage (except Michael Bloomberg, but we’ll get to him).

Biden’s declining polls are a reflection of the fact that Democrats are seeing a sad truth.  He is no longer their best and brightest.  I like Joe Biden, who’s a good classical politician with his heart in the right place.  He can’t be President, and he won’t.  Even if he did get the nomination (spoiler alert:  he won’t), Donald Trump, five years younger, and without a moral bone in his body, will have him for breakfast. 

Mike Bloomberg

Now let’s talk about Michael Bloomberg. 

In this cycle, Wednesday night was our first direct exposure to Bloomberg, and he was terrible.   One performance may not be entirely fair, but we already know his reputation as a poor speaker and debater who often seems to care very little what people think of him.  That’s a good attribute for a CEO/entrepreneur, sometimes, but not in a politician.  At least, you can’t let people know you don’t give a shit what they think.  You at least have to be able to hide it.

That doesn’t mean that Bloomberg cannot win the nomination (or the Presidency).  Never underestimate the impact of a billion dollars.  He just starts with some disadvantages.

It is true that he was mayor of the country’s largest and most complicated city, New York, for twelve years, and despite some negatives was a very successful mayor (especially compared to his predecessor, Rudy G.).  On the flip side, he is a rich New York Jew, which will lose him a few votes in some parts of America.  (Yes, I know that’s not fair.  It is just true.)

Winning New York three times means he knows how to win, and he certainly has the credentials for the White House.

On the other hand, in order to win, Mike Bloomberg will have to do at least three things (that we know of) and he has to do them fast:

  • Authorize any woman who has signed non-disclosures with his company to speak freely, as long as they tell the truth and they respect the privacy right of other individuals (excluding Bloomberg).  If he can’t take the “I have nothing to hide” approach when it comes to #MeToo, he loses the moral high ground to Trump, and is not a viable candidate.
  • Release his tax returns before Super Tuesday.  Similar to the non-disclosures, this is a transparency/nothing to hide issue.  Saying his taxes are complicated makes him sound like Trump.  As long as he’s just another billionaire, he is not going to win the nomination.
  • Make a public statement that the amount he spends to defeat Donald Trump is not in any way dependent on whether he is the Democratic nominee.  He has to say:  “I have decided to spend $1 billion to save our country from an evil President, Donald Trump.  Whether I am the nominee, or it is someone else, I will still spend that billion dollars on this election.”

Even if he does all of these things (he won’t), there is still only a small chance the Democrats will make him their nominee.   The spectre of two New York billionaires fighting over the Presidency will be too much for most Democrats, and a person who was a Republican in 2008 is always going to have a problem getting a nomination from the Democrats.

Tom Steyer

If we’re talking about billionaires, let’s not forget Tom Steyer.

Let’s be clear.  Tom Steyer is a child.  At 62, he is young enough to be the son of Joe Biden (or Bernie Sanders, for that matter). 

He is a billionaire (barely), but not in the same vein as Mike Bloomberg.  Bloomberg started and built his own company.  Steyer was a hedge fund manager.  He made smart decisions, and made lots of money, but he was solely a money guy.  He never actually built a real business.  (Of course, Bloomberg made his billions selling services to money guys, so there is less difference than first appears.)

What Steyer can claim is that, a long time ago (at least fifteen years), he saw the moral high ground and decided to go there.  He embraced socially responsible and environmental investing, and made it work.  He embraced charitable activities, and was successful at that as well.

Still, another New York rich guy (technically Jewish, but really closer to born again Christian) is going to have issues.  He is a true believer in liberal causes, and no-one doubts his heart is in the right place.  His major charitable activities go back decades, and he has been a supporter of the Democratic Party for almost forty years.  His credentials are much better than Bloomberg. 

But Tom Steyer suffers from not having the skills of a politician when he is placed on the big stage.  That should be a good thing, some say, but if you can’t communicate your message on a debate stage, or in a town hall, then your true believer status almost doesn’t matter.  You’re not going to be the guy.

Don’t count Tom Steyer out.  As a compromise candidate – more left than Joe or Pete, but not as much as Bernie or Elizabeth, and still a real live billionaire who believes in anthropogenic climate change, he would be viable.  He could unify the Democratic Party, offering something for everyone, and face Donald Trump head-on.  Backed by the whole party, he would be a formidable challenger to incumbent Trump.

None of this is likely, despite the underlying logic.  In some respects, it is too bad.  He might be the best choice for President among all of them… but he won’t be.  Unless Tom Steyer gets a major endorsement (Barack Obama?  Elizabeth Warren?  Joe Biden?) to vault him into the first tier of candidates, he is not going to be the nominee.

Amy Klobuchar

Next up is Amy Klobuchar.  If you look at this from a traditionalist point of view, she is the perfect candidate.  She is from the Midwest (although a consistently Democratic state), and she has been a successful at Yale, University of Chicago, and as a lawyer.  She won three Senate elections, the last two in landslides.  She knows how to win.

Klobuchar has also accomplished a lot as a senator.  In both Democratic and Republican senates, she has been effective in getting things done.  Her voting record is also solid on the issues that matter to Democrats today.

So what’s not to like?

The bottom line is confidence.  Whether Amy Klobuchar is actually self-confident or not (she probably is), she comes across as nervous or weak around strong personalities.  This is not a male/female thing.  No-one makes the same criticism of Elizabeth Warren.

The debate on Wednesday night was a perfect example.  Pete Buttigieg (and others, including Warren) attacked Klobuchar on her record and her policies, and Klobuchar didn’t show enough fight in her response.  She fought, sure.  Just not enough.  And this is not the first time.

She is a nicer person, perhaps, than the rest of them (Minnesota, you know – almost Canadian), but the willingness to fight is important in a Presidential election.  Even if you don’t accept that testosterone-style behaviour should be a prerequisite to the Presidency (I don’t), in fact it is.   Women still have to show they are at least as tough as men – while still being nicer than men – to be electable. 

Is it fair?  No.  Is it reality?  Yes.  Just ask Hillary Clinton.

Amy Klobuchar is another one that shouldn’t be counted out.  The Democrats may well go in this direction in order to select a moderate that doesn’t have the baggage of Biden or Bloomberg (see above), or Buttigieg (see below).  If they do, though, they had better invest a lot of time and money to get behind her in the election.  Otherwise, she will not beat the bully, Trump, in a general election.

Pete Buttigieg

Pete Buttigieg could be the grandson of Biden or Sanders (do the math).  That probably disqualifies him from the nomination already.  Does anyone know a 38 year old who is ready, today, to be President of the United States? 

This is despite pretty good credentials.  At the age of 18, he won a prestigious national prize with his essay on – you can’t make this stuff up – the political courage of Bernie Sanders.  He graduated magna cum laude from Harvard, won a Rhodes scholarship, and got his masters at Oxford.  He was a decorated soldier who spent seven months in Afghanistan, while he was mayor of South Bend.  He also speaks eight languages.

And, of course, he was mayor of South Bend, Indiana, a city of more than 300,000 people about 150 km east of Chicago.  He spent eight years as mayor, winning an overwhelming re-election in a small Midwest city despite coming out as gay before that election.  This is another politician who knows how to win (at least in heavily Democratic South Bend).

Oh, and one more thing.  He is an exceptional public speaker, sometimes called the “white Obama” because he speaks in complete sentences. 

But Mayor Pete’s youth isn’t the reason he is not electable.  Mayor Pete is gay.  Americans are not going to elect a gay President in 2020, much less one who is married to another man, and would thus have a “First Lady” who is a man named Chasten.  Mayor Pete might win in 2028.  He will not win in 2020.

I have a lot of problems with Pete Buttigieg, a career politician who is often far too smooth (i.e. slippery) for my tastes, but it is not his real failings that will lose him this nomination.  Instead, it is something that shouldn’t matter – his sexual orientation.  If just 2% of voters who would otherwise support the Democratic nominee are too socially conservative to vote for a gay man, Donald Trump will be re-elected.  Democrats know this. 

Sorry, Mayor Pete.

Bernie Sanders

That leaves us with Bernie Sanders and Elizabeth Warren, the socialist and the witch.

Bernie is another career politician: all politics, all the time for his full 78 years.  That means, depending on your perspective, that either a) he has never actually accomplished anything productive in his life, or b) he spent his whole life fighting for what he believes in. 

After ten years as mayor of Burlington, Vermont (population under 40,000 when he was mayor), Bernie was elected to the House of Representatives in 1990, and then the Senate in 2006.  In his almost 30 years in Congress, he has steadfastly remained an Independent.  He was the victim of cheating by some members of the Democratic Party in the 2016 Presidential election, and lost the nomination to Hillary Clinton.

By now, Bernie is an open book to all Americans.  Everyone knows what he believes in, and no-one – not even his worst enemies – doubts his integrity (well, maybe Trump does, but he doesn’t count).  He is a very good speaker with a distinctive New York style despite 52 years living in Vermont.  Many senators and representatives respect his intellect, his abilities, and his moral compass, even if they disagree with him.

Bernie, however, made a critical mistake:  he deliberately accepted the label “socialist”, saying he wouldn’t apologize for being a socialist.  As many Canadian columnists note, Bernie’s idea of being a socialist would put him in the mainstream in Canada, but a label is a label.  There are generations of Americans brought up to believe that socialism is bad, even dangerous.  America is different from other countries because it is not socialist, or communist, or any of those other bad things.  The American dream exists precisely because America has rejected socialism.

What this means is that everything Bernie says is filtered by voters through the socialist label.  Medicare for all is not like Canadian health care;  it is instead one step away from a “welfare state”.  And, it will cost trillions of dollars, so taxes will go up.  Way up.

While Bernie is trying to communicate that his policies are in pursuit of equality, not a welfare state, the socialist label is going to be pasted on his back like a target throughout 2020.  Not only will it hurt him against Donald Trump, but it will hurt those running down ticket – representatives and senators who will have to disavow Bernie’s “socialist” tendencies, or risk being painted with the same brush.

Bernie Sanders could probably save his campaign, and win the nomination, by selecting a running mate who is more middle of the road, and doesn’t carry any socialist baggage.  If he let it be known, quietly, that his running mate would be Kamala Harris, for example (assuming she could be convinced to support him, which she probably could), and she started stumping for him in key late voting states, that could take the edge off his socialist label, and make him electable. 

Sadly, Bernie is not likely to do that.  Perhaps that is exactly why he should not be elected President.  They say “politics is the art of the possible”, and Bernie knows that quite well after his decades in Congress.  If Bernie is not willing to do what is necessary – such as choose a moderate who is also a woman of colour to be his running mate – he is sending a message that he will not be an effective President. 

The polls say that Bernie Sanders would beat Donald Trump head to head.  Bernie reminds people about that daily.  Unfortunately, Bernie would not in fact beat the Donald in an actual election.  Socialism is acceptable to many voters in the big cities, which will go to the Democrats in any case.  In Michigan, and Wisconsin, and Florida, voters will not choose a socialist President.

The other wild card is the super-delegates.  If Bernie doesn’t have enough delegates by the time he gets to the convention – and I don’t think he will – then he will not be the nominee.  The members of Congress and others who are not pledged delegates will not choose someone who has always refused to be a member of the Democratic Party. 

Elizabeth Warren

Does that mean Elizabeth Warren is the one who will beat Donald Trump?

Ignore the political nuances for a moment, and just ask yourself whether Elizabeth Warren would be a good President.  Easily the most intelligent of the seven candidates, Warren has been a lawyer, a teacher (of special needs students), a Harvard law professor and author of five well-regarded law books, and a U.S. Senator.  Her history of championing the little guy while at the same time being an unabashed capitalist means you can trust her to do the right thing, but still do it well.  She is feared by Wall Street, all the while rejecting socialism and supporting the free markets.

Still on that theme, Warren is different from all of the other candidates in that all of her policies are well thought out, and in each case backed by a detailed plan.    

Now turn to the political side.  Warren has been a champion debater since high school, but that is intellectual debate, not political debate.  In a classical debate, none of the other candidates can touch her.  As a political debater, on the other hand, Mayor Pete and perhaps Bernie are better than Warren.

Warren has also been hampered by a tactical mistake.  Heeding the (incorrect) advice of her experienced political advisors, she adopted a stance and persona of unifier and voice of reason.  Still trying to look tough (see Amy Klobuchar, above), she also want to appear nice.  In short, she made the same mistake as Hillary Clinton.

The problem was that she didn’t really appear all that nice, and the persona she was wearing didn’t make her more relatable.  She is never going to be everyone’s buddy, like Joe Biden.  She’s always going to be distant, the “brainiac” who isn’t really like the rest of us.  All the fake persona did was make her appear weaker, and more like the other politicians on the stage.  

In the Nevada debate on Wednesday night, faced with declining poll results, Warren jettisoned that approach in favour of being the real Elizabeth Warren.  The real Elizabeth Warren has been called shrill, and harsh, and many other things.  On the other hand, no-one hearing the real Elizabeth Warren in the Nevada debate doubts that she knows what she’s talking about.

The result?  Standing next to poor, defenceless Mike Bloomberg, she savaged him so badly that you almost felt sorry for him.  Any doubts that she could handle Donald Trump were gone.  Her destruction of Mikey was proof of what will happen when she goes up against that other New York billionaire. 

Elizabeth Warren has lost some of her momentum, and it remains to be seen whether she can reverse that trend by reverting to the real Elizabeth Warren. 

Warren has improved her situation a little by her apparent informal selection of Julian Castro as her running mate.  Castro is a good politician who can tap voter demographics that will not naturally warm to Warren.  He is also a progressive but in a more moderate vein than Warren or Sanders.

The additional step Elizabeth Warren should take is to increase her emphasis on how moderate her positions are, relative to Bernie.  If she can position herself as more moderate than Bernie, yet more progressive than everyone else, she can still be the successful candidate in a close nomination fight.

And, of course, Warren vs. Trump is almost certainly a Democratic victory.  The only question is whether she can actually make him cry on national TV.  As a bully, that’s what he deserves, but she might still be a tad too nice for that.


It is too early to predict the winner of the Democratic nomination, although it appears unlikely that it will be Biden, Bloomberg, Steyer, or Buttigieg.  If Klobuchar can bring all of the moderate votes to her side, it could be her, but that is a long shot.  More likely it will be Sanders or Warren, and if those are the two final choices, my money is on Warren.

Of course, maybe that’s just wishful thinking.

  •  Jay Shepherd, February 21, 2020

About Jay Shepherd

Jay Shepherd is a Toronto lawyer and writer. This site includes a series on energy issues, plus some random non-fiction on matters of interest. More important, it includes the Lives series, which bridge the gap between fiction and non-fiction, and now some short stories. Fiction is where I'm going, but not everything you want to say fits one form. I am not spending any time actively marketing what I write, but by all means feel free to share if you think others would enjoy reading this stuff.
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6 Responses to Defeating Trump – Really?

  1. Bruce Sharp says:

    Jay, I hope you’re right.

    Liked by 1 person

  2. If one looks at the US government’s redistribution of taxpayer’s money, it is clear that much of the non-military spending Is indeed on technically speaking social causes. The New Deal was a Socialist venture. Furthermore one could view the US Military as a giant socialist job creation programme. One of the few universal common goods for Americans is a fairly well paying job in the Military.

    Liked by 1 person

    • Jay Shepherd says:

      True enough, Russell.

      I don’t think the U.S. public generally has a problem with social programs. Some of their social programs (like the GI Bill) have been major drivers of their successful society.

      But Americans still cling to the paradigm of self-reliance and independence, and see “socialism”, the word, as antithetical to that paradigm. If you were able to demonstrate to the average American that much of capitalism is exploitive of the weak by the strong (which it is), they would be lost, because their entire worldview would be upended.


  3. Mark Simpson says:

    Thanks Jay. I likely your analysis over these last two blogs.

    Liked by 1 person

  4. John DeVenz says:

    Thanks Jay. Excellent analysis.

    I believe Mayor Pete has a good shot at being the nominee, but you make a good case for why not. That said, if Obama was one of the candidates this year, would your analysis conclude he could not be the nominee because 2% of the US electorate that would otherwise vote Dem is not ready for an African American President?

    Below is an article that came out today by Rachel Bitecofer, a data analyst and election forecaster. Excellent article that explains why the dem’s did so well in the 2018 mid terms and why they should do well in 2020. In short, her analysis indicates there are more democratic than republican voters out there – and a hate for Trump will bring out those dem voters.

    Liked by 1 person

  5. Jay Shepherd says:

    John, both of your key points are fair ones.

    As for Obama, even though I have always been a big fan I would probably have rated his chances lower than other Democrats in 2008. On the other hand, he wasn’t going up against a dangerous incumbent, so I was still a Obama supporter.

    I read that New Republic article, and it is a good analysis. I am not suggesting that Bernie can’t win. I think he can, in large part by mobilizing a group of potential voters who would otherwise stay home. I just think that his path to electroal college victory is more challenging (because of places like Florida, which he cannot win), and I also think that the impact of a Bernie candidacy down ballot should not be discounted. Bernie personally can overcome the “socialist” label by his long history of consistent positions, i.e. his integrity. No-one thinks that Bernie is two-faced. He says what he believes, and always has. How many politicians have that? (Those who are attacking him for past positions have missed the point. A man of principle is a man of principle, i.e. Bernie. And, when facts show that a position is wrong, a man of principle changes his position.)

    Down ballot, there are a lot of more normal politicians, for whom socialism will be a dirty word. Even if Bernie wins, if the Senate and House are not strongly Democrat (due to the “socialism” factor) he won’t achieve any of his objectives.


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