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I say trade the older one if you can .... a decision I would make based solely on age. He's a sure bet for the HOF, a distinction that means nothing as far as the game is concerned -- its not going to help your fan base or anything, thus a total non-factor in the decision making process.
But his age may make a trade for top prospects difficult. His skills will be declining shortly, and every team you shop him to knows it.
So, that leaves investigating how value the younger one can bring in. He's in his prime, you might be able to swing a monster deal in your favor. As much as it would hurt to part with him, deals like that shouldn't be passed up if they come along (and that's a big IF since they're so rare).
In fact, if he really does get you a lot in return, I would even consider parting ways with both of them.
Obviously, my loyalty to my players is nil. I'm reminded of a reliever I once had on my team for a mere two seasons. I play out every game and make every in game substitution. I realized when I started shopping him around in the off-season that mentally I was calling him by the wrong name the whole time.
The point being, when I'm making lineups and/or substitutions, all I care about is the skill on the field. The name on the back of the jersey means nothing to me. I'd trade Jeter for your grandmother if I thought your grandmother had a decent curveball. Winning will get back any fans who get upset.
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