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After serving under three presidential administrations, hosting "Crossfire" on television and running for president twice, the pugnacious Pat Buchanan knows as much about political debate as anyone.

That makes the 76-year-old conservative ideally positioned to break down the challenges facing the 2016 Republican candidates for the White House in Cleveland on Thursday night. In another of my Speakeasy interviews, I sat down with Buchanan over dinner at a McLean, Virginia, steakhouse to run through the imperatives facing the sprawling field of 17 candidates, which will be divided into two separate debates.

Among his recommendations for key players:

Donald Trump: "He's shown a tremendous amount of political-athletic skills. People kind of like him, they like what he's doing. When he gives somebody a hard time, he does it with a smile on his face. He's a counterpuncher. ... He's going to have to take each of these things where he's been hit ... having a short, substantive answer.

"Don't try to, you know, show off your knowledge ... all the wonky stuff. ... The Fox guys are going to be after him."

Pat Buchanan
Mary Stevens | CNBC

Jeb Bush: "If I were Bush, I would challenge Trump directly and politely—maybe with a compliment thrown in at the beginning and a light comment. ... Make yourself stand out as though, this is Trump versus Bush. But make it more Bush-Trump.

"He's been unable ... to show the country a candidate who clearly is a superior candidate to the rest of the field. ... He's got to break out and be the leader."

Scott Walker: "One thing is not make a mistake. He's going pretty well. His problem is ... his trip abroad didn't come off well. He's got to show a measure of gravitas, and also of communications skills."

Marco Rubio: "He has a certain callowness and youthfulness. I think crisp answers, short answers, show some gravitas also. If I were him, I wouldn't roll the dice and get in a fight with Trump. I don't think that's going to help him or bring him up as the alternative. I think he's got to deal with his own problems rather than the Trump problem."

John Kasich: "I don't think there's any advice you can give John. He's decided what he's going to do. He feels we have to care about poor people. I don't know if it's going to work or not, but you've got to respect the guy for doing what he believes. He's a tough guy."

Ben Carson: "He stays Ben Carson. I wouldn't try to change. He's got the 10 percent. Don't do anything to damage that. Why get in a fight with Donald Trump?"

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Ted Cruz: "He does Ted Cruz. Cruz has real natural skills and talents. He's been to Harvard Law. He's a debater. He's a speaker. He gets crowds on their feet. I think Cruz is one guy that does have the potential to break out."

Rand Paul: "He should ... come out again as sort of an anti-interventionist against these wars in the Middle East. I would distinguish myself that way to try to get back into the mix against Bush."

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Chris Christie: "He's got a tough assignment. I mean, Trump has become sort of the uber-tough guy."

The seven lagging candidates in the nonprime debate: "Somebody is going to excel in the seven. And we're going to get clips off that. And those clips are going to go on Fox and MSNBC and CNN and CNBC and they're going to say, 'Here was the best exchange.' You shouldn't diminish the potential for that. You can build yourself up with some exchange, and maybe next week you're in the tournament."