Editor's note: When you think of New York City Mayor Bill de Blasio, “pragmatic” probably isn’t the first word that springs to mind. But that’s exactly what Joseph Viteritti set out to prove with his book, “The Pragmatist: Bill de Blasio’s Quest to Save the Soul of New York,” out this week. In the following excerpt, Viteritti argues that the mayor’s hesitation in endorsing Hillary Clinton for the presidency was more than just a political blunder – and that it reveals “a fissure in the de Blasio psyche”: a man of high-minded progressive ideals who nevertheless understands the necessity of compromise.

Bill de Blasio the pragmatistHillary’s senate race got a lucky break when Mayor Rudy Giuliani for health reasons cancelled his intended run. Rick Lazio, less well known than the hard-charging mayor, turned out to be more formidable than expected, but the woman from Arkansas prevailed, beating the Long Islander by twelve points.

In the meantime, press reports indicated that tensions had developed within the Clinton campaign operation. There were stories of friction between de Blasio and some people in Hillary’s high-powered Washington-based organization, who evidently held more sway. What could have happened? The answer to this question sheds light not only on the 2000 senate campaign, but also on de Blasio’s behavior toward Hillary Clinton in the more recent 2016 presidential campaign. And, I would argue that, taken together, the two pivotal episodes reveal the character of Bill de Blasio better than anything we have seen.

Let us take the two Hillary episodes in order.

According to de Blasio, he was somewhat ambivalent about the 2000 race at the start. One reason he offered was personal. As he explained, “I had two small children at the time and had just worked on a string of campaigns. I knew that taking on the senate campaign would require more sacrifice by my family.” The second reason he offered was professional: “I was not sure that I was prepared in this early part of my career to take on the enormous responsibility of running the first lady’s U.S. Senate race. It was a huge leap.”

Given his reservations, I asked why he agreed to do it at all, to which he responded in more detail:

I had no doubt she would be a very good Senator. But it was also necessary to beat Giuliani, and I believed she was the only person who could do it. I had been the New York State director for Clinton-Gore in 1996, which was the first time I worked in the Clinton world. And because I was working in the Clinton administration at HUD as a political appointee, I felt a loyalty to the Clintons. So when it was finally made clear to me in the fall of 1999 that Hillary wanted me to take the campaign manager role, I thought the right thing to do was say yes – despite the family challenges.

So what was the source of the friction that had been reported? According to de Blasio, “There were several reasons and they developed over months as the year 2000 progressed.” He explained, “Some issues were strategic, some had to do with key personnel decisions to be made, and some were philosophical.” On the latter, he elaborated when pressed, “There was a split within the campaign between the progressives and the moderates, and the latter won out.” With the benefit of hindsight, after what has happened over the past two years, the emergence of such a division is not difficult to comprehend.

Let’s now move to 2016. There it was apparent all along that de Blasio had certain philosophical misgivings about Hillary. But he never suggested that he would support anybody else, including Bernie Sanders, whose unswerving stance on economic inequality was more in line with de Blasio’s own predilections. He admits, “Although I opposed the DLC (Democratic Leadership Council) and its centrist politics, I had real hope for Hillary. I thought she would eventually take a stronger position on income inequality. She could have generated more support if she had taken a stronger stance, and done it sooner.” He continued, “I like Bernie Sanders, but I had a certain loyalty to Hillary going back to 2000 that I could not dismiss. And I also thought that she would do a better job at putting those ideas into action as president.”

The two Hillary episodes expose a fissure in the de Blasio psyche that helps us understand his place as an insider/ outsider in the political process – as a man who has strong philosophical commitments, yet appreciates the need to function within the system to have his goals realized; who understands the need to compromise, but is not entirely comfortable with its bargains. Bill de Blasio, after all, is the progeny of two prodigious personalities: an idealistic father who embraced Franklin Roosevelt’s New Deal aspirations, but was bitten by Joseph McCarthy’s Cold War hysteria; and a pragmatic mother who did not allow her high-minded ideals to overwhelm her Southern Italian predisposition against entirely trusting government to do the right thing. Bill de Blasio harbors similar doubts, but he soldiers on in a way that is confusing to those who are accustomed to the ordinary machinations of American politics. He can stun the regulars and dismay the dreamers.

De Blasio ended the 2000 campaign on good terms with the Clintons. Both Bill and Hillary Clinton continued to support his political ambitions and endorsed him for mayor once the party primary was resolved. Hillary was in attendance when the former president swore in the new mayor – an extraordinary gesture of friendship for a former first couple. There apparently were no hard feelings on their part about the Senate race.

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