David Boies
David Boies (Photo: Rick Kopstein/ALM)

Litigator extraordinaire and onetime “Good Wife” star David Boies knows his share of muckety-mucks, so it shouldn’t be surprising that he’s crossed paths with Donald Trump. (You’ll recall that Boies argued for Al Gore in Bush v. Gore before the U.S. Supreme Court.)

Just three days after the election, I attended a lunch at New York’s Union Club where Boies was being honored by the New York chapter of the Boys Scouts. Who knew Boies was once a Boy Scout?

After the luncheon we retired to the library, where we chatted about the election, his prognosis for the Supreme Court and, of course, what he thinks of the real Donald.

This election was a stunner. How would you compare Trump’s win to what happened in 2000 when you represented Al Gore against George W. Bush?

At the time we thought Gore and Bush were more alike than Clinton and Trump. This election is different because Trump won fair and square, whereas with Gore, the Supreme Court’s decision resulted in the election of Bush.

I’m not sure the fact that Trump’s presidency is legit is going to make people—or, at least, me—feel better. In fact, isn’t that worse?

I think it’s more frustrating. We felt that the stakes were high with this election, but we didn’t know that during the 2000 election, and it turned out to be extraordinary high. So maybe we’re overestimating how much is at stake now.

Do you have reasons for optimism about a Trump presidency?

I’ve known two Donald Trumps: The New York businessman who gave my oldest son his first job and the very loving father. Our daughters were classmates at Penn. Then there’s the second Trump: the campaigner who spoke in sound bites who displayed none of the intelligence and reflectiveness I’ve seen. And we might yet see a third Trump—the president. I’m hoping that he’ll be more like the businessman I’ve known for 30 years.

Stop. Did you say a “reflective” Trump?

He’s a showman but he’s also a very savvy businessman, negotiator and builder. The question—and I don’t know the answer—is to what extent is he going to feel he’s captive to the political process and continue to engage in campaign rhetoric, and what extent he will revert to someone who puts people together. The businessman will reach out to people he disagreed with because he had to compromise on every deal he did. As a candidate, he crushed everyone who disagreed with him. I don’t know what the Trump administration will be like, but if my only experience with him is only as a businessperson, I’d be optimistic. But if I only had the campaign to guide me, I’d be pessimistic.

Speaking of being pessimistic, women didn’t rally around Hillary as we had expected, despite Trump’s displays of sexism. What happened? 

The good news is that a very large number of men and the majority of American people wanted a woman to be president. She won by over 1.5 million votes. The bad news is the electoral college and the fact that women are not as invested in their own progress as other groups that have suffered discrimination. As a matter of pride, women will say ‘I won’t vote for her because she’s a woman.’ Because they’re in the majority, it gives them a sense of complacency. They’re also influenced by their environment—tradition, marriage, the views that their husbands have.

Let’s turn to the Supreme Court under Trump. Is there a chance that gay marriage rights will be chipped away?

No, I don’t think that’s going to change. It is so well accepted now that we can’t go backward.

What about “Roe v. Wade” and other liberal causes? Surely, the court will take a sharp turn right.

I don’t think [Roe v. Wade] will be overturned. It’s always hard to predict how people appointed to the Supreme Court will develop over time. Like the presidency, it tends to bring out the best in people. The issue is not so much conservative or liberal judges but whether they’re judicial activists. Some of the people on Trump’s list respect judicial tradition.

Since you know Trump and seem friendly with him, is there any chance he’d bring you on to bridge the divide between him and liberals?

I don’t see myself being asked. His first step should be to bring his party together. I think he ought to reach out to Jeb Bush and Mitt Romney. They lost, but he can take advantage of their expertise.

Rumor has it that if Hillary had won, you’d be a key player in her administration. True?

I’ve been a Hillary supporter for a long time, since 2008. There was no discussion, and, as we saw, there’s no point to do so before someone is elected. As for my taking a position, I think there are other people who are younger and more suited for the government.

You talk like you’re going into the sunset, but there’s no indication of that. Are you a bit sad that you won’t get to end your career with a high government position?

The only position I would have been interested in would be solicitor general, the one that Ted Olson held under Bush. If Gore had been elected, I would have been up for that. I feel I can contribute more doing the kind of cases I’m doing than holding a government position.

Contact Vivia Chen at vchen@alm.com. On Twitter: @lawcareerist.