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The Smart Money Is on Val Demings

The congresswoman / grandmother / former police chief is the best bet—literally—for Biden's VP.
June 17, 2020
The Smart Money Is on Val Demings
Rep. Val Demings (Shawn Thew - Pool/Getty Images / Shutterstock)

I’m going to do something I’ve never done here before and probably won’t do again. So bear with me.

I got a long—crazy long—email from a reader about Biden’s VP choice.

This reader is a professional gambler who bets on political outcomes for a living.

He does not want his name revealed.

So we’re just going to call him code-name “Domer.”

Anyway, Domer wrote for me a giant piece explaining why he thinks the literal smart money—meaning, sharp players making cash wagers—should be on Val Demings as Biden’s VP.

And the entire thing is so smart and interesting that I’m going to give the newsletter over to him so he can explain his thinking.

Ladies and gentlemen, good luck. Here’s Domer:


Joe Biden is likely to select Kamala Harris, a Senator from California, as his running mate about six weeks from now. Bettors arebetting on Harris. Pundits arepredicting Harris. Reporters arereporting Harris in the lead. And Kamala’s personal connection to Joe ispreviewing a possible ticket. But that could be a mistake and, in my estimation, an unforced error at a key inflection point for the campaign.

I’m betting, literally, that when the vetting narrows down the choices—when the pros and cons of all of the candidates they’ve interviewed are white boarded and chewed over and argued about in the context of what this race is really about—that a little known member of Congress, Val Demings, comes out on top.

Will this actually happen? Probably not! But it might happen, and bettors are starting to figure that out—the odds on Demings have shortened from 50-1 to 5-1 in the past few weeks. I hope to walk you through the process of trying to find and predict an unlikely outcome. An outcome that could provide a windfall profit, if my instincts are correct.

As a brief introduction, I bet on politics (mostly), and have been betting as my sole occupation since I put in my two-weeks notice in 2007.

In 2020 political alignment parlance, I’m a college-educated, “Never Trumper” Republican who has been realigned from a certain straight-down-the-ballot R voter to a certain, if unenthusiastic, Joe Biden voter. I primarily use a website called PredictIt (and before that, the now-defunct Intrade). PredictIt is a peer-to-peer exchange that allows users to bet legally with one another on all manner of political forecasts; the most popular of these forecasts revolve around the Presidential election. As a tradeoff to its legality, there are strict limitations imposed by the CFTC of $850 at-risk per contract, and the door to PredictIt is fully open to any academics who want to study what its traders are doing.

In order to make a consistent living, one needs to be right a bit more than wrong, and to occasionally be right on very unpredictable outcomes that people did not see coming. I wrote an article in 2012 discussing my process, and in it are stories about discovering a governor from Alaska named Sarah, imagining a Jon Huntsman Presidential campaign before it existed, and losing my shirt misjudging Barack Obama’s cabinet selections. In this 2020-focused article, I’ll dive deep into a single topic: Biden’s VP selection. My goal is to unearth one of those unpredictable outcomes that people did not see coming. For perspective on my recent VP selections…in 2016, I did manage to nail Mike Pence for Trump, but I lost money on Tim Kaine, thinking Hillary would make a more outside-the-box (read: smarter) choice.

Replaying the 2016 Election

The place to begin in Joe Biden’s vice presidential selection process is my analysis of the current general election landscape. Biden has a lead of 8.1% over Trump on RealClearPolitics as of June 15th; he is also a slight betting odds favorite to become our next President (~57% chance). It’s not a guarantee that Biden wins, though, and further uncertainty creeps in via the fact that Trump is running a VERY unconventional campaign.

The Trump strategy, in a nutshell, is to hop in a Delorean and recreate 2016, with the notable addition of expanding his base to include a larger share of disaffected minorities. (Quick aside: Trump’s “What do you have to lose?” outreach to minorities is the exact same phrasing he used when asked about the dangers of Hydroxychloroquine.)

In Trump’s 2020 plan, there are no outstretched arms to either independents or Democrats on the basis of his record or leadership, other than to hammer away at his polling advantage on the handling of the economy (an 11 point edge for Trump in a recent WSJ/NBC poll). He wants to rile up his base, and get them to the polls. If he can ensnare a few extra saps along the way, great news for Trump!

This plan, in my opinion, is idiotic, and I am guessing many Republican strategists would agree. It ignores the new math of his shrinking base as a percentage of voters, and it disregards how unpopular Trump is with the non-base voters that he needs to woo. But Trump is unmoored from strategists like few other politicians, and not without some reason: His own strategy already worked once! And it might work again with the same formula.

In order to replay the 2016 election, Trump will need to do two things: (1) Tear down Joe Biden to the point where he is disliked as much as Hillary Clinton was in 2016, and (2) Run as an “outsider” change agent who can fix America’s economy. (“I alone can fix [whatever these idiots are trying to screw up].”)

Immediate problems present themselves with Trump’s Back to the Future strategy. The first is that Biden has an enormous favorability gap over Clinton. The second is that Trump is now an insider incumbent who should not be able to realistically hoodwink voters into believing that he is still an outsider!

Joe Biden is, by almost all accounts, a genuinely good person who has deep friendships across political lines. This is his biggest edge against the antagonistic Trump.

To quote Lindsey Graham from 2015 (prior to Graham’s reputational seppuku) “[Joe] is the nicest person that I think I’ve ever met in politics…he is as good a man as God ever created.”

Biden may get overly handsy and may have a wayward son. He may make political errors and even try to take unethical shortcuts like ripping off another guy’s speech. You may disagree with him or even hate him politically. But it is fair to say that Joe Biden is a nice guy who means well, and it is equally fair to say that voters share this sentiment.

Biden currently has a -1 favorable rating (in 2020, this qualifies a politician for beatification) on RealClearPolitics. In 2016, at around the same time, Hillary Clinton had approximately a -15 favorable rating.

It is going to be a herculean task to implement Trump’s first 2016 redo strategy—to recast Biden as deeply unfavorable in the eyes of voters. This has already flopped badly in the first couple months of the 2020 campaign, and it’s unclear what is still left in the Trump arsenal.

Trump’s second strategy is to use the Men in Black zapper on voters, and run as the change candidate for his own re-election. We’ve already seen Trump preview this with some recent rants about all-caps OBAMAGATE, the scandal so expansive in scope as to defy explanation. We have seen it in his effort to constantly re-litigate and re-focus on the 2016 election—a time when he was not yet president and all of the status quo insiders were trying to prevent it from happening (in his re-telling). We’ve seen it in Trump’s abandonment of writing a new 2020 Republican platform at all. Instead, the Republicans simply plagiarized their platform from 2016, a move that is so dripping with post-irony that we should try to bottle it and use it to revive David Foster Wallace.

In the Trump campaign worldview, all good things that have happened since 2016 have accrued by Trump’s acumen, and all bad things that have befallen the country since 2016 are the fault of the previous bumblers in the White House. This strategy, which may justifiably strike the reader as insane, has a shockingly realistic chance of success.

Joe Biden has been an elected leader in Washington, D.C. since there were 4 channels on TV; he was sworn in 3.5 years after Neil Armstrong set foot on the moon. Biden has 8 years as a veep and 36 years(!) as a U.S. senator—oodles of experience and longevity, true, but also an opening for Trump to define Biden as “status quo.”

Additionally, Trump already defeated a candidate who wore out the cassette tape on her “Most Qualified Person to Ever Run for President” soundbite, and he is itching to run against the deep-state D.C.-types yet again. In Trump’s framing of the election, Trump is the dam preventing the forgotten man from being crushed by a raging flood of swampy water. Trump wants Biden at the political scene of all of Trump’s imagined Deep-State crimes, and he has an army of sycophants equally eager to place Biden there.

Searching for a Good Heart

Which brings us to the VP pick. My lens for picking Biden’s best running mate is a woman who does absolutely nothing to aid Trump’s dual strategies. A woman who will do no harm. This means that I think a career politician like Amy Klobuchar is a poor choice (irrespective of recent events), even though she seems like a good fit for the blue wave coalition that delivered so much success to Democrats in 2018.

It also means that I think a partisan firebomber like Kamala Harris or Elizabeth Warren is a poor choice, because then Trump gets to paint Biden with the brush of a well-defined and disliked liberal legislator from a liberal state.

These may seem like simplistic and trite ways to dismiss a candidate as flawed, but that doesn’t mean they’re unimportant. Trump’s dream is to mold Biden out of socialist clay; to define Biden in a way that, for instance, reverses Biden’s advantage with finicky senior citizens. Trump’s goal is to further define Biden as a puppet for liberal interest groups in Washington that want to destroy the country. Trump wants Biden’s gargantuan 25 point edge in a recent WSJ/NBC poll on “the ability to bring the country together” to evaporate.

The question Biden’s team should be asking is: Why give Trump any openings whatsoever to hammer Biden when the choice is in your hands?

And so my thinking goes that extensive D.C. political experience is a negative with the uber-experienced Biden already at the top of the ticket.

Also, we’re on the hunt for an agreed-upon good person, to reinforce Biden’s core strength and wall off a line of attack from Trump that would seek to close the gap on their favorability numbers. When Biden announced his candidacy for the presidency, he talked about a battle for the “soul of the country.” We’re looking for a potential VP who delivers on that contrast with Trump to the greatest extent possible.

Much like I typically do in these circumstances where I think the traditional favorites may be ill-suited for the task, I spent days reading Wikipedia articles for biographies, listening to politicians answering questions on Youtube, thinking outside the box on what a traditional VP pick is, and talking my quarantined wife’s ear off about all of this (needless to say, she’s eager to head back to work).

Out of that research, three names stuck out to me as “long-shot” fits for Biden: Tammy Duckworth, Terri Sewell, and Val Demings.

Both Tammy Duckworth and Terri Sewell are great people with phenomenal life stories that bolster Biden’s strengths.

Demings, however, is a natural communicator in the clips I watched, as compared to clips of Duckworth, and she had extensive experience in leading, as compared to Sewell.

In Demings, I’d found my dark horse candidate.

She was 50-1.

“Still I Rise”

I knew of Val Demings from following the Mueller investigation and the impeachment proceedings. In fact, I asked for a market from PredictIt on who the impeachment managers would be, specifically because I wanted to bet on Demings. (Luckily for the other traders, they did not put up the market; she was indeed a semi-surprise pick.)

My VP research on Val Demings started from a place of knowing her as an effective and thoughtful person in Congress, and that was about it. I read her backstory as the first step, and discovered that she was a former police officer who rose to police chief in Orlando.


Then I watched a video from a few years ago where Demings said offhandedly about being a rookie cop: “My plan was that I was going to go to the police academy, and just kind of stay under the radar and not draw attention to myself. And I was elected class president within a couple of weeks.”

After listening to that, something clicked.

I put together the three pieces in front of me:

  • She was the first non-lawyer to be an impeachment manager;
  • She rose to become chief of an organization dominated by white men;
  • She was elected class president in the early 1980s long before it was in vogue to elevate women.

There was something there. These are each tiny pieces of evidence on their own, but together they suggest that Demings is a natural leader who instills trust in her peers. She has been elevated to leadership roles in spite of disadvantages and because of that trust. Similar to her police academy story, I found an interview where Demings said she was not seeking to become an impeachment manager nor was she dropping any hints about being interested. Instead, Nancy Pelosi came to her with the idea and asked if she’d do it.

In the absurd circus that is American politics, where everyone is trying to climb ladders and raise their political profiles, the most powerful Democrat in the country came to Demings with the idea of leading the House’s case against Trump, instead of vice versa.

Cue Sally Field: “They like her, they really like her.”

Demings’ life story further boosts the case and is unmatched among the serious VP candidates, longshot or otherwise.

She grew up incredibly poor, a descendant of slaves. Her parents did not finish high school, and worked in low-skill jobs. Demings was sent across town to a segregated school until sixth grade. She was the first in her family to attend college, and put herself through Florida State University by working at McDonald’s. She became a social worker after college and then applied to the police department. After serving as a police officer for 27 years, culminating in the top job, she ran unsuccessfully for Florida’s 10th Congressional District in 2012 against a quasi-incumbent. She lost by 3 points, but outperformed Barack Obama’s 2012 vote share in that district by 2.6 points. She started and stopped an Orlando mayoral run in 2014 and then successfully ran in a reconfigured Florida 10th Congressional District in 2016, garnering 64.9% of the vote and outperforming Hillary Clinton by 3.1 points in her district. Republicans did not oppose her in 2018.

In the intervening years, Demings married fellow police officer Jerry Demings (also a rousing self-made success story!); they have 3 children and multiple grandchildren. Both she and her husband ride Harleys, and she is heavily involved with her church, counting Rev. Terence Gray as a mentor. Her biography is best summed up by Val herself:

“[My parents] worked hard, and so every day now when I look at what I’ve been able to accomplish…it’s a tribute to my parents. [When I became the chief of police], they became the chief of police. When I look at being a member of Congress, they became members of Congress. And so their sacrifices paid off. All of their hopes and dreams as Maya Angelou says in her poem “Still I Rise”: we’re ‘the hope and dream of slaves.’ What I have been able to accomplish…the hope and dream of my parents.”

Multiple facets of Demings’ life fit into Biden’s continued campaign emphasis on running for president to return decency to America and reward hard work. Her life is an embodiment of his message. Setting aside her police work in this moment of history—I’ll come back to that—blue-collar public service is legitimately hard to find in elected officials. The traditional feeders are law and military service. A former police officer has never been president (though Teddy Roosevelt did serve as a police commissioner). A police/blue-collar background also strengthens another of Biden’s strengths against Trump: senior citizens—a demographic where Biden has improved upon the 2018 blue wave coalition by yanking those voters from Trump—have strongly favorable views on police.

Finally, geography: Val Demings is from what is traditionally the most important area of the most important state in the country for a presidential election. The I-4 corridor in Florida runs east to west from the Atlantic Ocean, through Orlando, and on to Tampa on the Gulf Coast. It contains around 25% of the votes in the state. Additionally, Demings was born in Jacksonville and attended FSU in Tallahassee. If she took some vacations in Miami, she’d have a connection to every part of the state.

Does being from Florida actually matter, though? The evidence is mixed on whether vice presidents can statistically aid in higher vote share in their home state. My takeaway from the data is that a VP can definitely aid locally if the person has deep connections to a specific region, but not necessarily statewide. Long story short: it certainly doesn’t hurt representing such a vitally important part of Florida. It is a state where even a slight advantage is multiplied in importance by the nature of the Electoral College.

As Long as She’s not a Cop

Bearing in mind that I’m biased (and this should be front of mind for anyone reading this), I’ve also mulled over her shortcomings, namely a lack of political experience and the fact that she was a police officer.

Val Demings has only been a Congresswoman since 2017, which would traditionally be an immediate dismissal for a VP candidate’s chances. In talking with other people who bet on politics, many disregard her as an option because of this.

But I’ve found that elected experience simply doesn’t matter much.

Obama was a senator for 3.5 years before being elected president. The current president had 0 years of experience.

Voters do not care and any perception that they care is wrong. Sarah Palin did not flame out in the eyes of voters because of the length of time she held office. She flamed out because she was an inexperienced media surrogate and not particularly smart or savvy to boot. There’s scant evidence that voters would care about the length of Demings’ elected experience.

Plus, her track record would seem to indicate that she is an effective leader. Demings has also been spending considerable time as a media surrogate for Biden during this pandemic, likely so that the Biden campaign can evaluate her abilities.

Finally, Biden would be sneakily mirroring the Obama/Biden ticket with a Demings selection. An older white candidate with a long history of elected office paired with a more recently elected black official with a deep background of non-legislative experience.

Demings’ career as a police officer is the thorniest subject in the wake of the George Floyd murder and best encapsulated by a recent conversation I had with a liberal friend.

I talked about Demings being my top choice and explained some brief things about her.

He responded: “I’ve never heard of her, but if she’s not a cop, she sounds great.”


I had to inform him that she was exactly that! So…that’s a problem.

Or is it?

With the strong caveat that the vetting could turn up law enforcement skeletons (Florida’s Sunshine Law provides easy access to records of public officials), I’ve again decided that this does not matter. Controversial! And also quite convenient!

The reason I decided this isn’t complicated though: The demographics where Biden has made inroads into Trump, as compared to 2016, all approve of the police more than average. Biden is peeling off suburbanites, college-educated whites, and senior citizens from Trump. These three groups easily have the highest approval of police officers in their respective demographic groupings.

The voters who are distrustful of police are largely already Biden voters, unlikely to be disaffected or dissuaded by Biden’s choice in running mate. Trump will certainly not disparage police work—he tweets “LAW & ORDER” every 24 hours or so, as if he lost a bet to Dick Wolf—so who is going to attack Demings for being police?

My mind was also set at ease on this topic after reading some of the Orlando police department’s biggest critics during her tenure. Two lawyers who successfully sued Orlando for rights violations said they would be supportive of her VP selection in a recent story on Demings: “I think she found the appropriate balance of good community service and being aware and sensitive to the needs of the community and also recognizing and supporting good law enforcement” and “I support Val Demings…I think her heart’s in the right place.”

In addressing the two major drawbacks of Demings, I do not think I am wrong to dismiss objections to her experience, but my decision to dismiss objections to her policing may prove incorrect. My hypothesis that liberal voters would not be impacted by the Demings selection may prove to be a poor assumption. I do not have the resources to poll test such a specific question.

The Biden campaign, though, would have exactly that at their disposal. I would assume that if Demings is under strong consideration for the job, the issue of her police career will be put to the test with liberals. One of the reasons that Hillary Clinton lost (there were many) was disaffected liberal voters. My educated guess, however, is that police work as a VP’s main background would have zero impact on Democrat enthusiasm.

Because that enthusiasm revolves around deposing Trump.

My thinking on the VP selection process from today, in mid-June, through the selection around August 1 is that the Biden campaign is soon to narrow down a long VP list of anywhere between 12 and 20 candidates.

The campaign will get that initial list down to 5 or 6 eventually, and I think that final list will very likely include Kamala Harris, Elizabeth Warren, Michelle Lujan Grisham, Amy Klobuchar, Val Demings, and Tammy Duckworth. There’s also a possibility that Gretchen Whitmer, Susan Rice, Keisha Bottoms, Maggie Hassan, or Tammy Baldwin make the final list in lieu of names that I’ve mentioned.

My biggest leap forward in logic is that I think, ultimately, the choice will come down to Kamala Harris or Val Demings. They fit the moment and fit with Joe. On a personal betting level, the two options have quite different outcomes: I’d win $5,000 on Harris and $50,000 on Demings.

I am not totally dismissive of Harris’s chances. If Biden had to make the choice right now, without any further vetting, I think he would pick her without much thought. But I’d like to take a quick moment to hash out why I am skeptical of her chances after a thorough evaluation by Biden’s team.

First and foremost, it is true that Harris has been vetted extensively already as a result of running for president in 2019. It is equally true, however, that the result of that public vetting was a total disinterest from that same public in voting for her. Harris excelled at little, other than fundraising and some viral debate clips.

The good news for Joe is that regardless of whether Harris is his VP or not, she can still do fundraising for him and she can still be a quippy surrogate for him.

Secondly, prior to becoming a senator, her two runs for attorney general were unspectacular affairs in California politics. In 2010, she won by the narrowest margin of any of the major candidates for statewide office, and in 2014 she was in the middle of the pack. The best spin on her electoral history is that she does about as well as a generic Democrat, even with vast sums of money at her disposal. Harris also has a scandal in plain sight that will be fodder for swamp-obsessed Republicans: her boyfriend Willie Brown kickstarted her political career with two key appointments, for which she had zero qualifications—and he threw in a BMW for good measure. If life is a comic book, Harris’s origin story in politics is just plain icky, and it subverts many of the narratives that Biden already has going in his favor.

I think the “safe,” but well-defined, liberal senator from California is a mistake waiting to happen and one that would provide a jolt of energy to a Trump playbook that’s currently on life support.

If Demings versus Harris is indeed the choice in front of Joe Biden weeks from today, I think the woman born in Jacksonville—home of the newly-relocated 2020 Republican convention—should be on that stage.

A woman who pulled her parents along with her through segregated and integrated schools into college. A woman who pulled her parents with her through the police force. And a woman who pulled her parents with her into the halls of Congress, where she swore another oath to serve and protect, and led the prosecution of the current occupant who broke that oath.

And that’s where I’ve pushed in my chips. Wish me luck.

Jonathan V. Last

Jonathan V. Last is editor of The Bulwark.