I just started reading Jonah Keri's book The Extra 2%. I'm only up to chapter 4 so far and he's talking about the mismanagement that caused the Rays to field losing teams year after year.
He makes a point that losing teams are rewarded with high draft picks and successful teams are penalized with low picks. While I agree that this helps to level the playing field, there should also be some checks and balances. If a team (like the late 90's/early 00's Devils Rays) picks near the top for, say, 5 years in a row, they should move down in the draft order with the World Series winners. This would give teams a little more motivation to draft well and would be a more effective way to create more of a competitive balance.
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