He's the ultimate Cinderella, vaulting himself in 2008 from the type of obscurity reserved for the Summit League to victory against everyone's No. 1 pick.
But when it comes to bracket time, President Obama says "nope" more than "hope" to would-be Cinderellas.
Actually, they're almost certainly not. As the president himself knows, he'll sooner get John Boehner to flip-flop on healthcare than win Warren Buffett's billion-dollar bracket challenge.
And Obama - with his reliance on picking top-seeds - has again displayed his predilection for conventional basketball wisdom. He's actually proven not all that good at correctly making calls - and has been just plain bad at picking upsets, which are the real fun of bracket season.
Start with his Final Four this year: He picked No. 1 seeds Arizona and Florida to make it to North Texas. The president also sprinkles in two No. 4 seeds, Louisville and Michigan State, to go to the Final Four.
That's not as bold as it might look since the consensus on those two schools is that they were given short shrift by the selection committee. (That committee, it should be noted, prompts more second-guessing than any committee, super or otherwise, that Washington has yet concocted.)
The fact is that Louisville and Michigan State are among the tournament favorites. Then, in choosing a champ in Michigan State, the president is buying into the Tom Izzo system, after meeting with the coach earlier in the year, Katz told me.
"He's all in on Tom Izzo. Loves Tom Izzo," said Katz, who has filled out brackets for ESPN specials with the president since he took office. "Clearly, when Izzo met with the president earlier this year, when he was in East Lansing, that had some influence on him. And he's riding Tom Izzo and Michigan State."
Obama has previously cited his respect for Roy Williams in favoring North Carolina to go farther than they've actually gone. Carolina, it should be noted, was the president's one correct call for national champion, back in 2009 (see chart below), though Williams' video on behalf of the Obamacare website didn't get him much presidential love this year.
Among the lower seeds, I've previously been critical of how Obama could fill out a bracket without a single 12-5 upset. He actually picked two such upsets this year - Harvard and North Dakota State.
But the pick of Harvard - where Obama went to law school, by the way - would have had more cachet last year when the president whiffed on the Crimson's upset of New Mexico. And the president has exactly zero teams with double-digit seeds advancing to the Sweet 16. If that actually happens, "Sports Illustrated" may not have a cover story next week.
Also intriguing is how the president handles Wichita State. The undefeated Shockers drew what's surely the toughest bracket and Obama doesn't have them advancing past the Sweet 16. He does have them beating Kentucky in the third round, but then losing to Louisville.
As for political friends, sorry Joe Biden: The president has his veep's Syracuse team winning just a single game before being upset by Ohio State. He also has Delaware making an early exit - though, to be fair - Delaware grad Chris Christie also said he thinks the Blue Hens will get blown out by Michigan State on Thursday.
It doesn't look like the president is playing homer for Democrats - not with a Final Four that would make Marco Rubio, Jan Brewer, Mitch McConnell, and Rick Snyder all smile.
But it does look like Obama is displaying the kind of caution that's long frustrated some of his supporters. Notwithstanding his bold decision to challenge Hillary Clinton way back when, he's been more careful in choosing his political paths just as he has choosing paths through the tournament.
|2008||North Carolina (E1) Kansas (M1) Pittsburgh (S4) UCLA (W1)||North Carolina (E1) Kansas (M1) Memphis (S1) UCLA (W1)||North Carolina (E1)||Kansas (M1)|
|2009||Louisville (M1) Memphis (W2) Pittsburgh (E1) North Carolina (S1)||Michigan State (M2) Connecticut (W1) Villanova (E3) North Carolina (S1)||North Carolina (S1)||North Carolina (S1)|
|2010||Kansas (M1) Kansas State (W2) Kentucky (E1) Villanova (S2)||Michigan State (M5) Butler (W5) West Virginia (E2) Duke (S1)||Kansas (M1)||Duke (S1)|
|2011||Ohio State (E1) Duke (W1) Kansas (SW1) Pittsburgh (SE1)||Kentucky (E4) Connecticut (W3) VCU (SW11) Butler (SE8)||Kansas (SW1)||Connecticut (W3)|
|2012||Kentucky (S1) Missouri (W2) Ohio State (E2) North Carolina (M1)||Kentucky (S1) Louisville (W4) Ohio State (E2) Kansas (M2)||North Carolina (M1)||Kentucky (S1)|
|2013||Louisville (M1) Ohio State (W2) Florida (S3) Indiana (E1)||Louisville (M1) Wichita State (W9) Michigan (S4) Syracuse (E4)||Indiana (E1)||Louisville (M1)|
|2014||Florida (S1) Michigan State (E4) Arizona (W1) Louisville(M4)||?||Michigan State (E4)||?|