When it comes to The Oprah Winfrey Show, there is hardly a moment that passes where there isn't a mention of body fat, weight loss or something fitness-related. So it's no surprise that her personal trainer, Bob Greene, has built his own mini-empire around Ms. Winfrey's well-publicized gains and losses. His first book, Make the Connection: Ten Steps To A Better Body — And A Better Life published in 1996, was co-authored with Oprah and unsurprisingly hit No. 1 on the New York Times bestseller list. He published several more books and launched the Best Life Weight Loss Challenge with his mentor in 2007, urging a group of her viewers to sign up to drop the pounds. It worked for many of them, but when a 200-lb Oprah appeared on the January 2009 cover of O, The Oprah Magazine asking "How did I let this happen again?" it left some wondering where she and Bob had gone wrong.