WASHINGTON — Hillary Clinton was set to give a prime-time speech at the 1996 Democratic convention in Chicago. The stakes were high, all eyes would be on the first lady, and she’s not a natural at this sort of thing.

Upping the ante: Just two weeks earlier the wife of her husband’s political opponent, Elizabeth Dole, delivered a convention speech that wowed the country.

Clinton’s team was privately worried. Very worried.

“I really thought this was going to be the end of Hillary,” her then speechwriter, Lissa Muscatine, recalled, as she watched her boss struggle to use the teleprompter for the first time. “She was so bad. She was terrible on the teleprompter practice. I just didn’t know how she was going to pull it off.”


But Clinton did what she always does in these situations. Rote repetition, aided by one of the party’s top speech coaches. The process might not have been pretty (Muscatine, who described the anecdote during an event last year at Georgetown University, said she watched some of it in “horror”). But it paid off in spades.

The audience “hung on every word” of her speech and she “stole the show,” according to an account published the next day in the Chicago Sun-Times.

As Clinton heads into the second presidential debate, it’s evident viewers can once again expect her to be keenly prepared, because it’s in her nature to turn to the same strategy. Clinton is great at hitting the books, retaining ideas and fact and deploying them as needed. She has an excellent command of detail. She is known for demanding detailed advance briefings for the smallest event — even just a call with a reporter.

The downside is it means Clinton can come across as excessively rehearsed, cringeworthy and easy to parody, throwing out overly scripted lines like the “Trumped up trickle down economics” line she bandied about in the last debate.


Sunday’s town hall-style debate format is trickier for someone who is fact-driven and homework-oriented like Clinton. It rewards those deft at making an emotional connection with the audience and voters. Or, put another way, seeming human.

Clinton’s history of handling questions at town halls is mixed. Instead of pausing to absorb the emotion from a poignant tale, and respond to it, she tends to pivot directly to policy proposals or a plug for her website.

There may be good reasons for her reluctance to ad-lib. Her sense of humor tends toward the dry and sarcastic, which does not always play well for the home viewer.

During one town hall in New Hampshire during the primary campaign — Clinton was thrown off balance by a question about the $675,000 she received from Wall Street banks for giving a series of speeches.

“That’s what they offered,” Clinton glibly replied.

The remark was damaging and a mistake that Clinton’s likely not going to repeat, because she tends to learn from her mistakes.

Reporters camped outside her Chappaqua house have chronicled the comings and going of Clinton’s prep team over the past week.

And her team is happy to keep expectations high.

“Hillary did a lot of town hall debates and a lot of town halls during the course of the primaries and into the general,” said Clinton campaign chairman John Podesta after emerging from a prep session last week.


“She’s very used to the format. She likes it. She likes answering questions from individual citizens and she listens hard and relates to people. That’s a format that Donald Trump isn’t as used to, so we’ll see. I think it’s a natural format for her and she likes really engaging with people.”

The tendency to prepare, and even overprepare, goes beyond this one moment in the campaign, and gets to the core of who Clinton is. She always, always wants to be ready.

“She likes to know what she’s walking into,” explained Karen Hicks, a Democratic strategist who was a senior adviser to Hillary Clinton’s 2008 campaign.

“What’s the scene? What’s the sequence of events?” Hicks recalled Clinton asking. “From the strategic level of ‘What’s the best way to state the case?’ to details of ‘What am I going to be doing exactly? Who’s going to be in the room?’ ”

Hicks, who helped Clinton navigate early state primaries in 2008, said that Clinton obsessed over meeting with the top editors at local papers, particularly the Des Moines Register which is the most influential paper in the first in the nation caucus state.

Preparing for it involved a process Hicks characterized as “absolutely remarkable.”

Clinton not only wanted to know who was going to be attending, but also wanted to understand what their history was on individual issues, Hicks said.

“She knew a lot about every single person in that room,” Hicks said. “She has pretty magnificent recall.”


The staff work to get her up to speed does require an immense amount of time and attention. “It does force a whole level of organization around her,” Hicks said.

Other examples abound: Before Clinton held a 2008 editorial board meeting with the Concord Monitor, she read roughly 40 editorials that the paper had recently published, according to Judy Reardon, a New Hampshire Democrat who helped Clinton get ready for the meeting.

Clinton’s insistence on preparation isn’t limited to events that will help forward her political career.

Retired Admiral James Stavridis, who was the supreme allied commander of NATO while Clinton was secretary of state and briefly considered as a vice presidential pick for Clinton, recalled a meeting Clinton attended in Brussels about the Balkans.

The diplomats were, he said, “struggling to convince opposing parties to work together and maintain a shaky peace.”

“The depth of her knowledge about everyone at the table, including second and third tier EU diplomats and relatively unknown Balkan officials, was staggering,” Stavridis recalled.

“After the meeting I complimented her team on her level of knowledge and they said, ‘It’s really simple, admiral. She actually reads all the paper we prepare, and asks a ton of tough questions in the pre-brief.’ ”

Another reason why Clinton comes off as prepared and scripted is because that’s how her thought process works, those who work with her say.

“This woman thinks and talks in perfect paragraphs and sentences,” said Muscatine, her former speechwriter. “Sometimes she’ll stray off and digress in ways that drive people nuts. But it made it easy because if she’s kind of downloading to you, it’s coming out in very articulate thoughts.”


That was a contrast from her husband, whom Muscatine also wrote speeches for.

“With Bill Clinton – it would be like the best college seminar you’ve ever been in,” she said. “It would be amazing. But then you’d be like – oh, what am I going to do with all this now?”

Annie Linskey can be reached at annie.linskey@globe.com. Follow her on Twitter @annielinskey.