This is at least half playing devil's advocate, but I think you can make the argument that you should order based on record, but reverse the order for non-playoff teams(best non-playoff team drafts #1, worst record drafts 18th). The thinking being: - Both the current draft and IFA are investments in long term success, a team's outlook for at least the next 2 years has very little to do with their draft pick except in rare circumstances. The team with the worst record in year 1 has a similar ability to improve in year 2 whether they draft 1st or 15th(heck the draft isn't until after the ensuing offseason happens anyway) - In a world with draft pools(which I'll assume as a practical exercise are here to stay) draft position carries extra meaning because it's not just the difference between drafting 4th and 2nd, it's the difference in the money that can get spread across many players. If you have draft pools, you need to change the incentive to maximize them. By flipping the record order, you force people to make their MLB teams better and more watchable in the short term if they also want to have the maximum chance to make the team better in the long term. Crucially, this is not an either/or financial proposition because higher draft pools are a drop in the bucket financially. - This has the knock on effect of making MLB free agency more competitive. Teams right now can spend nothing on the MLB team, cycle through cheap roster flotsam to try to unearth an asset or two(think Valbuena and Coghlan from the Cubs rebuild), but remain bad enough to maximize their prospect spending to get a wave of prospects worth supplementing with free agents or high contract trades. If teams are incentivized to make their short term fortunes better in order to maximize their long term futures, then prices rise for that FA lower/middle class that has recently taken a big hit. - The MLB draft and IFA are still lotteries in their own right so even a team doing their best and still failing miserably can still draft/sign smartly and improve their fortunes. Plenty of valuable and even star players come outside the Top 5 so you aren't resigning a bad team to an indefinite fate of being terrible. Plus they can always just go into Dombrowski mode and use any prospects as currency until they're able to get out of the hole somewhat.