How to Go After Hillary

Some politicians are inadvertently generous to their opposition, graciously sinking themselves so others don't have to. John Kerry donned spandex waterwear and kiteboarded. Dan Quayle misspelled "potato." Howard Dean emitted what may have been a roar. But Democratic presidential front runner Hillary Clinton is not that kind of candidate. There's a reason she hasn't lost an election since she ran for president of the student council in high school. She does her homework; she doesn't do gaffes. Anyone running against her would be wise not to count on an implosion. So if she won't do herself in, how can she be beaten? We asked those who've run against her for lessons they learned trying to compete against such a formidable and careful candidate.

1. Give Susan Sarandon a call. When Jonathan Tasini ran against Sen. Clinton in New York's Democratic Senate primary in 2006, he was surprised not to get more help from Hollywood, considering how antiwar he was. He says he was told that although some in the entertainment community liked his position on the Iraq War and didn't want her to be president, they were reluctant to take her on. Back in New York, several Democratic elected officials privately encouraged Tasini, but refused to be seen in photos with him. One even looked around to see if anyone was watching before talking to Tasini at an event. Sarandon, the activist actress, wasn't intimidated, though. She came right out and endorsed him.

2. Keep the electricity going. Mike Long, chairman of the Conservative Party in New York, says that when Sen. Clinton walks into a room, her star power creates a glow in the air. "But as she performs, the light gets dimmer and dimmer," he says. "It's like a broken wire that doesn't deliver light to the other side of the room."

3. Stay behind your podium. When Rick Lazio invaded Mrs. Clinton's personal space during one of their debates in the 2000 Senate race, he made her look vulnerable. Lazio learned the hard way that a vulnerable Mrs. Clinton is a popular Mrs. Clinton. "Oh, do I remember the first focus group after that happened," says Bill Dal Col, Lazio's campaign manager. "[They said] 'he reminds me of my ex-husband.'"

4. Don't lose Page 10. Jeanine Pirro's campaign for Clinton's Senate seat in 2006 never recovered after she lost part of her announcement speech. As the cameras rolled, she let 32 excruciating seconds of silence tick by while she looked for it. Not good when your opponent exudes competence. (Pirro, who declined to comment for this story, has since left politics and is pursuing a TV career.)

5. Study Mike Gravel. Every candidate with something to lose sounds canned in the debates. Tasini sees an opportunity for someone to stand out as genuine—and attract voters—by sprinkling in some of the freewheeling, popped-his-lid style of the former Alaskan senator. Well, maybe keep the lid partially on.

6. "Raise money, duh!" That's Tasini, who believed his positions were more popular than Hillary Clinton's among Democrats—but since he raised only $250,000, no one knew it. Or who he was, for that matter. When he was out on the street asking people to sign his petition, he talked about her history. "People were shocked to hear she sat on the board of Wal-Mart for years. People were shocked to hear she'd voted for the war. A lot of union members still don't know that she has supported free trade." The money will allow a candidate to tie her to her positions, he says.

7. She voted for it before she was against it. Long suggests reminding voters that she has been on "all four sides" of the Iraq War issue. "There's plenty of clips that can be used in a good TV commercial that will quickly display her different positions. Early on [for example] she was trying to outdo George Bush," he says. Tasini agrees and thinks Barack Obama, particularly, should do more to exploit her Iraq vote. "When she says, 'We can all agree this is George Bush's war,' it's so false!" says Tasini. "You don't have to be abusive, but you can say, 'With all due respect, senator, you voted for the war, you supported the war. And voters need to take that into account for how you'll make decisions in the future.'"

8. Don't be like her. Long says that the Republicans have to pick a candidate whose views are different enough from Clinton's in order to motivate the base. Put that together with her high negatives and you have a chance at winning, he says. Former Yonkers Mayor John Spencer, the GOP nominee against Clinton last fall, echoes Long: "When candidates run away from their core beliefs they are destined to lose. If you are a Republican, run as one."

9. Get a good daughter. Dal Col says Chelsea Clinton is Sen. Clinton's secret weapon: "When she showed up it had the perfect effect. She humanizes her." And the fact that she's somebody's mom makes it more difficult to go negative on her, he says. "At the end of the day she's a mother and look at the child. No one can throw stones there."

10. Be grateful just to compete against her and you may get an invite to the White House. Nonna Noto, now at the Congressional Research Service, ran against Sen. Clinton in the Wellesley student government elections in the spring of 1968. She has vague recollections of the race but says she was lucky to become Hillary's vice president. "She has been very generous and invited the entire class to the White House twice. We hope to be invited along again if she gets elected," she says.