His father and his son both picked Villanova to win the March Madness NCAA basketball tournament. But when Bill McDermott, CEO of business software giant SAP, bet $10,000 in Bloomberg LP's "Brackets for a Cause" pool, he made what looked by the numbers to be a rational decision: Like a plurality of the boss gamblers, McDermott picked Kansas, betting with his head, not his heart.

The grandson of NBA Hall of Famer Robert McDermott, a Long Island parochial-school gym rat, McDermott started coaching the game with his Dad when he was 12. In slighting eventual winner Villanova, McDermott bypassed his hometown favorite, the school down the road from his Main Line home, the college where his friend Father Peter Donohue O.S.A. is President, the sanctuary where he attends Sunday Mass when he's in town, to make a cold calculation.

And it worked: McDermott still won the $420,000 pot -- and donated it to the charity of his choice, the Network for Teaching Entrepreneurship, which trains city kids "to develop an entrepreneurial mindset" and pitch business plans -- because none of the other 41 CEOs in the pool picked the Wildcats, either. Kansas was favored by 16; UNC, 13; Michigan State, 7. Virgina and Maryland, 2 each; Indiana and Oregon, 1.

So McDermott  won on points - he had UNC, correctly, losing in the final. He picked, in all, 46 of the 63 winners, besting No. 2, Starwood Capital boss Barry Sternlicht, who picked 43, and such high-powered competitors as T-Mobile boss John Legere, Salesforce.com founder Marc Benioff, Dallas Mavericks owner Mark Cuban, Goldman Sachs President Gary Cohn (who won last year), Cisco Systems' John Chambers, Microsoft cofounder Steve Ballmer, and Bloomberg's own Michael Bloomberg.

McDermott gave the pot to the Network for Teaching Entrepreneurship, which has worked with SAP since 2006 to help city and rural kids from "under-resourced" high school communities to "develop an entrepreneurial mindset and succeed in our innovation-driven economy."  

"My son Michael had it right from the beginning. He won his pool. He told me Villanova was going to win it all," McDermott told me the day after.

"I said, look, I have a chance to donate $420,000 to an organization I really support. And I want the Network for Teaching Entreprenurship winning my pool.

"We've been working with these kids for 10 years. These are kids like I was: in most cases they don't have any money. But they have dreams. They have ideas. You should see them present their business plans. Their winners' dreams. This wasn't lighthearted. I wanted to win for them.

"I had Villanova going a long way. But I had Kansas beating them. I was so happy when I was wrong.

"I celebrated with my wife and son in our home in Villanova as if the Jets won their second Super Bowl. (McDermott grew up on Long Island.)  I was proud to watch that game and be part of Villanova. And in our world at SAP, I was able to do something for a cause we care about..

"I love the game of basketball so much. My grandfather (Robert McDermott) was a Hall of Fame basketball player. I started coaching as my dad's assistant when I was 12. I coached my kids in the peewee leagues.

"I was so impressed last night by Jay Wright and his leadership. What really got me is, the first half, they were a little rocky. But they had a heart.

"Jay Wright made all the right defensive changes. He moved his team up. He took away the easy threes.

"One thing in particular I truly loved. When Jenkins took the [buzzer-beating, game-winning 3-point final] shot, Jay was on the next move: 'What do I do?' He was so focused on the next move he didn't notice for a second that he's won the game. Those kids were beautifully coached. They were inspirational. They played team basketball to an art form and I loved every minute."

His Dad picked Villanova? "My Dad still shoots the lights out of the basket at 76. He sent me a text last night, he said, 'This is a masterpiece coaching job.' He knows the science of the game. He predicted Villanova would win.

What does it say about American business that none of the CEOs picked the winner? "Very good question. I think what I see here is people that want to win." No sentimental choices? "That's the situation.

"The money goes to charity. In the end, it's about competition. Putting your money around who you really think has the best odds of getting it done.

"You have to understand (by Monday night, after McDermott's first pick had been eliminated), if Villanova didn't win those $420,000 wouldn't have gone to those kids. Once they beat Kansas I had to have them win it all. The others, they thought I'd get knocked off. I had UNC getting beat by Kansas, not Villanova.

"If it wasn't the greatest game of all time it was in the top three, of the history of basketball. I'm just so impressed with the leadership, teamwork and execution." Outside the game, McDermott specially praised Wright for taking time to exalt his predecessor and teacher, Rollie Massimino. "That humility. That's leadership."