Frank Rich is always good and even better here citing Halberstam (whose writing I love). Rich reminds us that "The Best and The Brightest" title ironically captured the narrative that unfolded - how Kennedy's bright advisers led us into Vietnam. It's a great book. And Rich does a service reminding us here in his column: The Brightest Are Not Always the Best.
And he's not so worried about Obama's security team, but rather the economic, reminding us that these guys pushed along bankign deregulation under Clinton. (They did the same in my field - telecommunications - I remember being incredulous and arguing a lot with my friends in the field).
He finishes with Rubin - and doesn't even mention the worse. But he says enough and in the end says that Rubin absence now may show Obama to be bright and wise.
Don't miss story of what Sam Rayburn said to Johnson. For history buffs, it's a great book.