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Look, Jackson's simply not ready. If he can't make consistent contact in AAA, he's not going to do so at the MLB level, Yes, this can be improved. It can be improved through experience and coaching. While he may not be ready right now... there is still half of this season remaining, and he is improving right now. He could very well end up showing signs that he's ready come September. He could go into next ST and win the job by proving he's ready. 3 months is forever when it comes to development.
I say give him the rest of this season at Iowa, along with Vitters who is looking more and more like he's getting close to ready. Let them both play winter ball. Then let's see where they are when camp opens up in February. Another year (from now) in Iowa won't hurt them, and it really won't set the team back either.
There is the possibility of trading guys like Jackson and Vitters who have upside but also obvious flaws. But I don't really see how that benefits the team as it doesn't make sense to trade prospects for prospects, and since the team isn't contending short term, they can't really start going after elite MLB talent either.
Jackson won't be in his theoretical prime for another three or four years so waiting isn't a big deal in my opinion. Vitters is also really young. I wonder if they have considered trying Vitters in the OF since his defense kind of sucks, but I don't think he has the power to stick there. I guess for most prospects, if they end up being good role players you count your blessings.