As has been famously chronicled, the Clintons and Bushes are pretty good frenemies. Not long ago, George W. and Bill were yukking it up yet again at the launch of their joint Leadership program—an initiative I thought was an Onion parody until I looked it up. Only two years ago, Jeb himself gave Hillary a medal for dedicating “her life to serving and engaging people across the world in democracy.”
The Clintons know that not-so-deep down the Bushes are basically Greenwich Republicans who are only too happy to pal around with them in private, when they don’t have to pretend to be hardcore conservatives. The Bushes are fierce competitors, to be sure, but they are also very predictable. They will hire the same people, with the same strategies and arguments as they always do. The kind of guys who led Bush 41 to a polite defeat against, well, the Clintons.
All great leaders need a little crazy—a willingness to depart, sometimes radically, from what the media and their opponents might expect. Determined to appear pragmatic, reasonable and uncontroversial, Jeb’s the candidate least likely to surprise the Clintons. He’ll argue for cutting taxes by a modest amount, argue for trimming spending just a tad, urge incremental changes in government programs and avoid any positions or statements that might raise anyone’s hackles. In hit TV parlance, if Donald Trump is “Empire,” Jeb is “Webster,” but without the cute little kid.