1888 King Kelly $6,429,543
1913 Frank Baker $6,697,127
Also, I have what's arguably the most valuable pick in the draft, with the first pick in the last round. If anyone is interested in exploring a trade for it, shoot me a sitemail. It would take a lot but I'm at least willing to listen to offers.
One other note -- rbow made a good callout to me earlier via sitemail. There used to be a way to draft players out of position in the Draft Center (i.e. Mark McGwire at Catcher) with some manipulation of the URL when you wennt to actually draft the player. I don't remember how to do this and think it's likely most owners don't even know it's possible, so I want to be clear that each owner is responsible for having a legal team with no manipulation. That means you must draft at least one hitter who can be drafted into each position's slot. Otherwise, it would be an unfair advantage for those who know how to do it. I would have flagged this earlier but I simply forgot it was possible.