The first time was in response to Holt bringing up Trump's longstanding support of so-called birthers who insist that President Barack Obama was not born in the United States. "He has really started his political activity," Clinton said, "based on this racist lie that our first black president was not an American citizen," adding that "Donald started his career back in 1973 being sued by the Justice Department for racial discrimination. Because he would not rent apartments in one of his developments to African-Americans." After addressing the birther issue ("I was the one that got him to produce the birth certificate and I think I did a good job..."), Trump circled back to the Justice Department suit and threw in his first objection to Clinton's ads. Here it in context:
As far as the lawsuit, yes, when I was very young, I went into my father's company. We, along with many, many other companies throughout the country -- it was a federal lawsuit -- were sued. We settled the suit with zero, no admission of guilt. It was very easy to do. But they sued many people. I notice you bring that up a lot. And I also notice the nasty commercials you do on me in so many different ways, which I don't do on you. Maybe I'm trying to save the money. Frankly, I look at that, and I say: Isn't that amazing? I settled that lawsuit with no admission of guilt but that was a lawsuit brought against many, many real estate firms, it's one of those things.
Trump's second ad reference came when he was trying to address Clinton calling him out for his history of misogynist statements.
Holt: Mr. Trump, just take 10 seconds, and then we've got the final question.
Trump: Hillary is hitting me with tremendous commercials. Some of it's said in entertainment, some of it's said to somebody who's been very tough to me, Rosie O'Donnell. I said very tough things to her and I think that everybody would agree that she deserves it and nobody feels sorry for her. But you want to know the truth? I was going to say something --
Holt: Please, very quickly.
Trump: -- extremely rough to Hillary, to her family, and I said to myself: I can't do it, I just can't do it, it's inappropriate, it's not nice. But she's spent hundreds of millions of dollars on negative ads on me, many of which are absolutely untrue, they're, and they're misrepresentations, and I will tell you this, Lester, it's not nice, and I don't deserve that, but it's certainly not a nice thing that she's done. It's hundreds of millions of ads. And the only gratifying thing is I saw the polls come in today, and with all of that money --
HOLT: We have to move on to the final question.
TRUMP: -- over $200 million spent and I'm either winning or tied. And I've spent practically nothing.
Trump's mind may have been on ads because through the day on Monday, leading up to the debate, his campaign released and re-released a slew of commercials on social media attacking Clinton, including this one titled "Do You Really Need to Ask?":
Simon Dumenco, aka Media Guy, is an Ad Age editor-at-large. You can follow him on Twitter @simondumenco.