Trey Grayson got a first-hand and early look at Rand Paul's political talents in the 2010 Senate Republican primary, where Paul upset the establishment-backed Grayson - a major moment in the tea party wars that came dominate the year.
Grayson, now from a perch as director of Harvard's Institute of Politics, has begun to mend ties with the Kentucky senator, who recently appeared on stage with Grayson at Harvard. Grayson now sees Paul as a potential frontrunner in the 2016 presidential contest.
"He's obviously extraordinarily talented with politics. He's I think got a good sense of timing. He's got a message that is resonating with Republican Party voters right now, and he's a serious candidate," Grayson told me and ESPN's Andy Katz, in the latest episode of our podcast series "Capital Games."
"I think he's got a real shot at being the nominee. It's too early to say whether he's the favorite or not, but he's certainly someone to be reckon with. Some of the things that I saw that he did quite well in running against me, he's continuing to do that," he said. "For the Republican Party to win more elections, we've got to do a better job of bringing younger voters into the fold, and Sen. Paul certainly does that."
Grayson also said he believes Kentucky's other senator, Mitch McConnell - who endorsed Grayson over Paul in the 2010 race - will cruise to the GOP nomination in the primary race later this month against tea party favorite Matt Bevin.
"The only question in that race is the margin," he said. "I think Sen. McConnell will be fine, but I think just the question is the margin. I felt that for a long time and there's nothing to make me think that there's going to be any kind of surprises."
We brought Grayson on to share tales of politicking at the Kentucky Derby. It's important that Kentucky politicians - or other pols who attend the Derby, for that matter - pick a horse and are prepared to explain their choice, he said.
"You did need to be able articulate a reason for why you were for that horse and people talked to you about it and then also - you had to go to the Derby," he said. "It was an important place for politicking, whether you were a state legislator, or a statewide officeholder, or a statewide wannabe."
Grayson said the Derby is a unique political event because it's one of the few major sporting events that takes place in the same place every year. It's a must-attend event for politicians and other public figures, including those from the world of sports, he said.
"If you think of Cal [University of Kentucky Coach John Calipari] and Rick [Pitino, of Louisville] are both - they're public figures and they're kind of politicians," he said. "Their supporters of their programs, their donors are there. People think it's cool to get their picture taken with them - I got my picture taken with them that day. So it's important for them to get around."
"Capital Games with Katz and Klein" is a part of the new podcast series, ESPN Perspectives, with original programming on issues across the sports world. The program explores the intersection of sports and politics, through interviews and analysis, and can be downloaded free via iTunes. This episode also includes interviews with Coach Pitino and Alison Lundergan Grimes, the Democratic candidate for Senate in Kentucky this year.