So at the time, as u may recall, Jackson was not projected to be the excellent disciplined hitter that he has turned into. Instead, the knock on him at the time was that he might not translate into a major league star because of his lack of plate discipline and his high strike out rates.
MY whole point is AT THAT TIME many scouts and the Yankee brass included viewed AJAX's potential ceiling as a Curtis Granderson type player. The line of thinking at the time was that they had no certainty of how AJAX would develop and if he had a Granderson like ceiling than why not take the safe route and trade him for the player we hope he turns into since that player is available, still young, and under team control. Its the safe play if AJAX busts and in the off chance AJAX does develop than even though you'll regret losing AJAX youll have a decent consolation prize. ITs hedging your bets and taking the uncertainty of the prospect out of play.
I wanted to use the line of thinking and philosophy that was utilized at the time of the trade as an example of the philosophy I prefer. Obviously in this case AJAX developed and overcame is strike out issues but there was just a good a chance he wouldnt have. The point is Im okay with parting with young prospects for young proven players, I just cant stand when we do it to acquire aging veterans.
Im sorry if I didnt explain myself well enough but I hope you see my point now, and in hindsight yes I would prefer to have Jackson but there were alot of question marks about him at the time of the trade. And Jackson is far from a proven product, he averaged .268 over his first two seasons in Detroit with about 175 strike outs per year and a combined 14 HR's. This season is much better but does it mean he will continue this trend or revert back to his career norms.