Shattered

If you’re still hurting from Hillary’s defeat and looking for catharsis, look elsewhere. Shattered is not for you. This book, which gives a thorough, readable, and authentic insider’s account of Hillary’s operation from the beginning of the email server to her troubles with Bernie to her stunning loss in November, is a sympathetic but ultimately a scathing indictment of Hillary’s 2016 campaign. While many pages are dedicated to the dysfunction and confusion inside the campaign team as they muddled through scandal and controversy, the most damning judgments are reserved for Hillary herself. If you read this book and still consider yourself a Hillary fan after seeing how she treats her staff while repeatedly refusing to acknowledge her own limitations or accept responsibility for her decisions, we simply have different definitions of leadership. While I think Hillary would make a better president than Trump, I left the book doubting that her presidency would be much better. Put another way, I’m sad Trump’s president, but I’m not sad that Hillary’s not president.

A lot of time in the book is spent portraying the dysfunctional dynamics between the various factions in Hillary’s campaign apparatus, and while those passages were entertaining, I think they’re also misleading. I don’t believe dysfunction, rivalry, and internal hostilities automatically lead to defeat. If it did, the 1991 Bulls wouldn’t have won the Finals and the Kobe-Shaq Lakers would have never made the playoffs. While there are other plausible explanations, I don’t think we can ever say with confidence why she lost. At the risk of misquoting Taleb, I remember an observation of his that trying to understand history is like speculating on the shape an ice cube by studying the pool of water it made after it melted. There were numerous conflicting factors that possibly led to her defeat (the Comey letter, anti-Establishment mood of the electorate, voter distrust, Democrat fatigue, inadequate turnout, complacency, possible voter suppression, the Kremlin, etc.) and trying to single one out as most significant or to calculate their individual impacts strikes me as interesting but somewhat futile. The reality is we’ll never truly know what happened, and if anything, reading this account made me less certain than ever about why things unfolded as they did.

Instead, what I thought was most eye-opening were the details surrounding Hillary herself as well as some of the actions she took during the campaign, and most of the rest of this post is dedicated to those details. Six things truly stood out to me:

  1. Hillary was haunted by her 2008 loss.

To her credit, Hillary was determined to not repeat her mistakes in the 2008 primary against Obama and she made some fixes. She focused much more on analytics, relied on outside experts hired for their competence instead long-time confidants hired for their loyalty, and worked very hard to reduce leaks to the outside world. However, in some ways, she arguably “mislearned” or learned the wrong lesson. For example, she thought Obama won almost purely because he had a better and more disciplined campaign team while her team was disloyal. While I’m sure there’s some element of truth, it also reflected her complete inability to see her own flaws and weaknesses as a candidate. She’d end up focusing a lot of time on building a competent campaign staff, but she never asked herself “What were my flaws? How can I connect better with the average voter? Why were there so many people in the Democratic party and my own camp that were so quick to stab me in the back and jump ship to the Obama machine?” It’s this last question that led to some disturbing behaviors like …

2. Hillary snooped her own people’s emails and then made an enemies list.

In order to find out who was leaking to the press and who was faithful to her, she decided to secretly re-read all of her team’s emails during the 2008 campaign. The image of her invading the privacy of her subordinates in order to sniff out disloyalty is already somewhat Nixonian, but then she and Bill created loyalty scores for each Democrat, and actively campaigned to purge them from the party. This ruthless focus on loyalty above all else wasn’t new. For years, the Clintons notoriously punished disloyalty (real or perceived), and while it was undoubtedly effective over the years, it had alienated many within the Democratic ranks. This frustration with the Clintons was enough to give Obama a sizable amount of superdelegates early in the 2008 race before his victory was inevitable, but that wasn’t the case in 2016.

3. Her ability to co-opt the Democratic party establishment was astounding.

No candidate entered a primary with more institutional support than Clinton in 2016. Despite higher levels of popularity and likability, both Bernie and Biden always ran into roadblocks when they tried getting institutional support. While Clinton has many flaws, she’s a phenomenal operator, and her ability to quietly and assiduously cultivate coalitions is incredibly impressive. This ability to garner institutional support was her greatest strength in 2008, and it was even more of an asset in 2016. But whatever gains she made in operational ability in those 8 years was somewhat offset by one of her key weaknesses: understanding voters.

4. Hillary’s inability to connect to the electorate was even more astounding.

While Hillary’s near total lack of self-awareness is maybe her worst attribute, even she could see that she was unable to understand the electorate. Throughout her campaign against Bernie, she and her staff expressed dismay at their total inability to gather a pulse for the party base along with Bernie’s ability to excite them. Whatever strength they had within Democratic institutions was almost totally offset by her inability to connect and understand Democratic voters. As I read this account, I was constantly reminded of the aphorism that “generals fight the last war.” Probably no candidate so thoroughly studied her own mistakes from the past and was more determined to correct them, but she also had zero ability to sense what was needed in the future. She was all execution and no vision, and the fact that neither she nor her campaign couldn’t say why she should be President was a problem from day one and would plague the campaign until her eventual defeat.

5. Hillary’s incapable of handling criticism.

In addition to Hillary’s lack of vision, another recurring issue was the Clintons’ (both Bill and Hillary) inability to accept personal criticism. Clinton was flummoxed by the email issue, and she repeatedly chastised her team for not putting the issue to bed. You can just feel her staffers wanting to say “Maybe when this came up, instead of going to your lawyers and coming up with the most legally defensible lie, you should have been upfront and apologized? Maybe voters distrust you because you see being honest with them as a secondary concern?” But nobody would dare the challenge the Clintons like that for a simple reason: the Clintons would have fired them. One of the interesting paradoxes about Hillary is that there’s no shortage of people who’ve worked with her who have nothing but glowing things to say, but she’s publicly reviled. Ezra Klein has an article where he attributes this dichotomy to gendered expectations of a political behavior, and I think there’s definitely truth to that. But there’s also no denying that anybody who questioned the Clintons’ judgment, or told them a hard truth they didn’t want to hear, or even considered themselves an equal was purged from their inner circle. The result was a lot of yes-men and loyalists more concerned with keeping their access to the Clintons instead of telling them what they needed to hear, i.e. the type of people who are only going to say amazing things about the Clintons to others. I’m sure this also explains why Hillary became so disconnected from the voters, since nobody in her orbit had the authority or courage to fundamentally challenge her world view.

6. Hillary lack of self-awareness and inability to take responsibility might be unprecedented in American history (except for Trump himself).

While the election night loss was tough on a lot of us, I’m sure the person who was hurt the most was Hillary herself. It was definitely the most humiliating loss in American politics since Dewey’s loss to Truman in 1948, and at some level, I felt a deep amount of sympathy for her. But after seeing how she’s responded to that loss, that sympathy is entirely gone. It’s not only that Clinton refuses to accept responsibility for her loss, but she doesn’t seem to understand the very concept of accepting responsibility. You don’t need to read this book to get the litany of excuses from her. Just check out her CNN interview, Recode sitdown, or this Fox news graphic (and then I’d recommend never having anything to do with Fox News again). But what really shocked me was that she partially blames Obama for her loss, since she felt he didn’t prosecute the Russia interference aggressively enough. I doubt any sitting president did more to get somebody elected than Obama’s campaigning on her behalf. The fact that she’d have the gall to partially blame him for her loss (while taking zero blame herself) was maybe the most shocking detail I got from this book.

Final Thoughts

Ultimately, what caught my attention more than anything else were Hillary’s failings as a person. Other reviewers focused on these details (like Vox), some focused on campaign dysfunction, and others focused on the arrogance of the Democratic establishment in general (like Rolling Stone). Regardless, there’s a lot of juicy details in this account, and if you like political narratives (ex: Game Change) or want to get a sense of the pressures inside a modern presidential campaign, I think you’ll enjoy this book. With that said, a couple parting thoughts.

1. You can lack self-awareness or an ability to connect to the electorate, but not both.

There was one person in Hillary’s camp who saw the danger signs before anybody else, had her ear, and did their best to warn her: Bill Clinton. I don’t think anybody would mistake Bill as a paragon of self-awareness, but I think even his harshest detractors would say his ability to connect to the electorate is exceptional. There’s been plenty of successful politicians that weren’t particularly reflective or self-aware (Bill, Reagan, Trump ) but were able to compensate for this defect because of their ability to connect to the voter. Similarly, I’m sure we’ve had politicians who weren’t particularly good with voters (ex: Bush 41), but at least had the humility to acknowledge their weaknesses and did their best to address them. Unfortunately for Hillary, she had neither, and it might have cost her the Presidency. If I had to boil these issues down to one sentence, it would be “Hillary blamed her staff because they couldn’t tell voters why she should be President.”

2. We’re in a critical period, do we need execution or vision?

To be clear, most of Hillary’s shortcomings (poor management, lack of self-awareness, not to mention campaign dysfunction) are Trump’s shortcomings as well, and I voted for Hillary in both the primary and general election. I don’t regret those votes, even if the thought of them makes me throw up in my mouth a little. But in a lot of ways, I think my opinion of Hillary’s higher than the average voter. I actually think she’s a decent person who means well, who takes her job seriously, works diligently, isn’t corrupt, and tries to do what’s best for the country (even if at times she conflates the country’s interests with her interests). And voters actually really seemed to approve of her in an operational role; her approval rating as secretary of state was 66%.

But that doesn’t mean I think she would have been the President we need at this time. In this blog post, Ben Horowitz says you can think of executives as either Ones and Twos. Ones are the visionaries who get people excited and motivate the employees, while twos are the operators who execute that vision and get things done. When a company’s able to have one of each at the top (ex: Gates and Ballmer at Microsoft, Jobs and Cook at Apple, Page and Schmidt at Google, Zuckerberg and Sandberg at Facebook), it can lead to amazing success. From that lens, you can argue the Obama/Clinton team (or Obama/Biden) was one such partnership, and Hillary’s the consummate Two. Oftentimes though, this can lead to succession issues, as the Two is the obvious choice to replace the One. But a lot of the time when a One steps down, what the company needs isn’t better execution but new vision and leadership, which by definition isn’t the Two’s strength. The result can be listlessness and mediocrity, as the Two focuses on continually executing a plan that becomes increasingly outdated (ex: Ballmer at Microsoft).

As I previously stated, Hillary is a phenomenal operator but had no vision. She couldn’t articulate why she should be President to her own staff, let alone articulate a compelling vision for the country at a time when the vast majority of Americans felt the country was on the wrong track. As a nation, we’re sailing into some pretty stormy waters — the ticking demographic and entitlement time bomb, massive amounts of government debt, possible disruptions caused by AI and automation, the transition to a knowledge based economy, climate change, the decline of the international order in place since World War II, the weakening of nation states, the surging of sectarian conflict, a loss of faith in American institutions. Not to mention the toxic partisanship that makes any change excruciatingly difficult to enact. These are all massive challenges, and I suspect we’re in the process of fundamentally rewriting the social contract that’s governed American life for nearly 70 years. My guess is many American voters sensed that they needed vision at this time, and they chose candidates like Trump and Bernie with flawed (and in my opinion, obsolete) visions instead of a candidate with none at all.

3. The future’s bright.

So no, I don’t think this book isn’t going to make you feel better after reading it, but there was one silver lining that made me optimistic about the future. At Hillary’s convention, the most powerful moment didn’t come from a Hollywood bigshot, New York financier, or Democratic power broker but from Khizr Khan, a gold star father and a Muslim speaking on behalf of all Americans who felt maligned and excluded by Donald Trump’s candidacy. It was one of the few, if only, moments of authenticity and decency in an otherwise toxic and degrading election season. It was the most powerful political moment I’ve witnessed since Obama’s 2008 Philadelphia speech, and to this day, nearly a year after he gave this speech, I can’t watch it without being brought to the verge of tears. When I re-read the portion of this book about Mr. Khan’s speech, I felt that same level of emotional intensity I felt then, and it reminded me that despite featuring the two worst candidates in modern US history, there’s still a lot of good people who are working hard and sacrificing for this country.

Hopefully one of them runs in 2020.

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