The Yankees payroll was $60 million more than the Cubs--which is too big of a different to put them in the same category. The Yankees have an incredible margin for error. I wasn't comparing the Cubs to the Yankees as much as I was the Cubs to the rest of MLB. The Cubs payroll was higher than any playoff team not named the Yankees: ~$5M > PHI ~$50M > SF & MIN ~$60M > ATL ~$75M > CIN & TB ~$90M > TEX The Yankees, Cubs, and about 4 or 5 other orgs. have a pretty huge monetary advantage over the rest of the league. But it's not the most important component. The two WS teams this season operated with payrolls at 47% & 27% of the Yankees'. They run their organization well and are popular, so does that mean they deserve to get all the top free agents? If the Badgers football team is run well & wins a lot of games, do they deserve to get better/the best recruits? I think MLB needs to invest in some "Yankee-proofing" to allow other teams to have a chance to share in the limelight. Imo this would require a salary ceiling (which many small market owners would love) & a salary floor (which many small market owners would hate). There's a reason MLB doesn't have a salary floor, and it's because small market owners would make less money. To get to your point about what's fair, what, realistically, should be done about the Yankees? There are always people to point out how they have an unfair advantage, yet what are the realistic solutions? The Yankees make a ton of money -- should MLB randomly seize some of that money from them? Should they not be allowed to spend the money they have on their team? I understand why smaller market fans get annoyed with the Yankees' financial reserves, but I don't really see a fair solution in terms of what should be done. What are some tangible ideas to "Yankees-proof" the system? EDIT: To answer my own question, one idea I just thought of would be to make every free agent signing result in draft pick compensation. The instance I'm thinking of is, of course, the Yankees signing Teixeira in addition to Sabathia two offseasons ago. First, I would like to see the free agent rankings completely scrapped & re-devised (the way Elias & MLB rank FAs is archaic at best). From there, create "types" or "tiers" of free agents, down to the FAs signing MiLB deals -- and create draft pick compensation for everyone above that (lowest) tier. Structure rules surrounding FA signings so that, any time a team signs a FA, the team losing said FA receives draft pick compensation relative to the status of the departing FA. You could still incorportate (and even expand) sandwich/supplemental picks, but I think the main impact would be to have teams lose their draft picks when they sign FAs. Even if a team signs multiple top-tier FAs, they would forfeit their highest remaining draft pick(s), in addition to sandwich-round compensation, relative to the FA's tier status. However many tiers of FAs there would be in any given offseason, that's how many sandwich rounds there would be generated in the draft (if that makes sense). This is just a crude thinking-out-loud type of rambling, but I think the only real way to get teams to reconsider spending ungodly amounts of money on free agents is to have it wipe out their draft picks. I'm sure there are plenty of logistical holes in this idea, but I hope the premise is at least reasonable.