"For the teams that are behind closed doors prepping candidates for this debate, the biggest challenge they have is figuring out the answer to the question: 'How do you go after a guy who has nothing to lose?'" said Kevin Madden, a former spokesman for 2012 Republican nominee MItt Romney.
The short answer, Madden and other campaign veterans say is discipline and good counter-punching when Trump unleashes wild swings and furious jabs. The question has been posed to candidates over the past few days and most land on some variation of "avoid him."
"I'm not going to take anybody, I'm going to say what I'm for," Wisconsin Gov. Scott Walker said when asked by Fox News Channel's Megyn Kelly on Monday night how he would handle Trump.
But one strategy, Madden said, would be to pull the wool back from Trump's game.
"People think they know Trump, but what they're really seeing is a TV character," Madden said. "One effective strategy would be to reveal that, with Trump, it's all an act."
Trump laid out his own plans in the last few days, but also played down expectations -- a rare move for the blustery Republican frontrunner.
"I don't want to be unreal. I want to be me. I have to be me," Trump said this past Sunday on NBC's Meet the Press. "We have enough of that in Washington with pollsters telling everybody what to say."
He made similar statements while overseas in Scotland last week, a different tone for a man otherwise full of bluster and bravado.
"I've never debated before. I'm not a debater," he said during a trip to Scotland. "You know these guys debate every night of their life, that's all they do is debate. They debate all over the place and nothing happens. I'm sort of the opposite. I have no idea. I am who I am. I'll show up, i look forward to it, and that's all I can do. I have no idea how I'll do. Maybe I'll do terribly. Maybe I'll do great."
Trump's antics have dominated media coverage of the Republican primary battle for well over a month now, rocketing him to the top of most GOP polls and virtually assuring him a spot on stage at the first Republican debate, which will be hosted by Fox News in Cleveland.
Beginning with his comments on immigration
in his announcement speech in June, Trump has dominated the national stage. And his comments about John McCain's war record -- which drew the loudest rebukes from his Republican opponents
-- only congealed his popularity among a subset of Republican voters.
"Trump is probably the King of Zingers so I don't think you want to play on that ground," Brett O'Donnell, who is doing debate preparation for South Carolina Sen. Lindsey Graham, said on CNN. "I think you want to be an effective substantive counter-puncher with him. You want to make sure that the people see you as a serious candidate for president, that you are competent for the job."
The goal for each candidate, he said, will be to make sure the press is writing about their best talking point. But that's a tall order with The Donald on stage.
Meanwhile, the candidate in question has been prolific on Twitter, sniping away at his perceived chief opponents at the front of the Republican pack. His chief target was former Florida Gov. Jeb Bush for weeks, but he recently shared his focus to include Walker, who is edging him out in Iowa.
Where Trump sees an unvarnished -- and incredibly wealthy -- truth-teller, his opponents see something far different.
"Imagine a NASCAR driver mentally preparing for a race knowing one of the drivers will be drunk. That's what prepping for this debate is like," tweeted John Weaver, a top adviser to Ohio Gov. John Kasich.
Frontrunners, like Walker and Bush, have largely been able to ignore or dismiss Trump. But once Trump is one of the 10 on stage, the potshots will be unavoidable.
Former Rhode Island Gov. Lincoln Chafee, a former Republican seeking the Democratic nomination, laughed when asked about how you deal with a wild card like Trump.
The best defense, Chafee said, is experience. He recalled his first run for mayor in Warwick, Rhode Island when he faced off against a Democrat and an independent.
"Taking down a (Democratic) machine is hard enough alone, but to have an independent wild card -- very glib, very outspoken, didn't care what he said -- was a learning experience," Chafee said at a Christian Science Monitor Breakfast last week.
Successful debaters stay on point and stick to their message, Chafee added.
"That comes with the territory, to be able to spar and parry. But the main thing is to be able to share your vision," he said.