Jess Jackson is IMO motivated far more by ego than by money. This is a man who is all about not letting others get the better of him, of having people look up to him and admire him as a leader and a canny "player." While I believe that he genuinely admires his horses Curlin and Rachel Alexandra as magnificent competitors, I also believe that if the horses ever stopped winning for him, if buying them was suddenly perceived as being the action of a fool rather than a savant, he'd lose interest in them very quickly.
When Jackson was being interviewed after the Preakness, I was surprised at how frail he came across. He's 79 and it might be that some of the effects of aging are starting to show. It's my observation that when a man who is motivated by ego and pride starts to slip, he can be susceptible to manipulation by people close to him, and I wonder just a bit if this is happening with Jackson. I don't know his family connections but it's possible that not everything he says or does is originating with him.
What's also true is that a man who is used to being perceived as a leader and as a sharp player can be erratic and just plain foolish when he feels himself starting to lose it. I don't know that this is happening to Jackson, but I wonder.
I suspect that if Jackson's top-dollar purchases of horses in training went wrong and he felt that people were starting to regard him as a fool rather than a savant, he'd very quickly back away from racing. The man doesn't need money, but people with as much ego as he has need constant ego-stroking. I think that the reflected glory of owning a horse like Curlin or Rachel Alexandra, of having "proven" that he was smart by purchasing them, is what makes Jackson happy, far more than the money the horses have won. The admiration he gets as Rachel Alexandra's owner, and the power he feels of owning the horse that right now is the biggest draw in the sport, is what stokes him, not the money she wins or her value as a potential broodmare.
