I think if you just say, "give me the top 10 spenders this year" that the numbers will tell you that. However, it is a cyclical thing. Being a top 10 spender absolutely helps you win. It's just that by the nature of the beast that it's going to come back to bite you at some point. However, you'll get many swings of the bat at a championship whereas a team like the Brewers will get 1 swing for the prize and a very shrewd team like Oakland or Tampa Bay will get 2-3 swings. In a decade, a big spender might get 5-7 and they'll be big ones. Look at this year's 2014's top 10 spenders. Everyone laughs at Philly's management of late. It's true that the contract for Howard and not dealing away their aging players was known to be silly. That said, they have a World Series from a lot of the guys they are paying and a few other shots at it. Yankees are paying for theirs as well. Red Sox are up there. Tigers and Rangers are top 10 spenders and have probably been the 2 "best" overall teams other than San Francisco in the past 5 years but fell a pitch short. So everyone sees the tweet from some baseball writer that the game is level because 3 of the top 10 payrolls were horrendously bad but about 18 fanbases from the bottom 20 would trade out their past decade for Philly, Texas, or Detroit's (save the heartache of losing several World Series). Even Boston is top 10 and "struggled" last year. I haven't crunched the numbers but I bet if you take the top 10 payrolls in 2014, you're going to have like 70% of the World Series participants and deep playoff runs in the span of 2005-2014. The Cardinals, A's of late, and Tampa Bay are going to be the only threat to that number and they are probably the best-run teams in baseball. EDIT: I crunched said numbers and if you use 2014's payroll you have this: -50% of WS participants were top payrolls in 2014. -In the past 10 years, 7 of the WS winners were top 10 2014 payrolls. 2 were the Cardinals (at 13th in payroll) and the last one was the White Sox exactly 10 years ago who finally dropped out of "big spenders" in 2013 or so and are now spending again. -I'll make this somewhat arbitrary looking at that last bullet point since CWS and HOU have blown it up recently, but let's cut it to 9 years and say "top 10 payrolls plus St. Louis." In said span, we have 18 World Series teams. 15 of them were top 10 payrolls in 2014 or the St. Louis Cardinals.