One of the reasons they overpaid was because of timing - it was in-season. Melvin used to say that pitchers are worth more in-season and hitters are worth more in the off-season. The fragility of arms, compared to bats, tends to lead to greater demand in late July, thus inflating the return. And in late July teams know exactly what they have and whether they are legitimate contenders, further inflating demand. Managers are paid to win games, GMs are paid to win championships. Theo was hired for one job - to end a 100-year-old streak. He did exactly that, and paid a price for it. If you look at what that championship has meant to the Cubs revenue - ticket demand and prices have skyrocketed, the area around Wrigley has been built up with a hotel, restaurants, park, condos/apartments, etc. - I don't think the Cubs owners have regretted what he gave up one bit.