God I'm tired of this endless debate. It's always a black and white conversation where one side says losing is the way and the other side bashes the cubs for being losers. The world isn't black and white, rather gray. Even with an amazing farm system the cubs are quite unlikely to be the '27 yankees. They're also unlikely to be what they are now. If you want a realistic look at where they will be look to the current Royals team since in 2010 they had "the greatest farm system ever." Those royals currently sit 52-50 and have been a fringe playoff team the past two years. You can make a valid argument that the cubs will have more payroll flexibility and should be at the very least slightly better given the Royals had to trade away 3 of their top prospects to get Shields.
Is that all that bad? I mean yeah you'd hope after all these losses that the end return is a title. But that royals team is likely to have a 5-10 year run of at least this level of success. Some years will be better than others and if they get the other right pieces to go along with it they could have a special season. Look no farther than the mid-2000's white soxs to see what I mean. For the first 4 years of the decade they were a slightly above .500 team. In 2005, they got the right parts and it lead them to a title. In 2006 they also won 90 games but didn't do enough to win the title or even make the playoffs.
The game isn't about having the best player at every position. It's about giving yourself enough of a base that you're in position to win if the cards fall right. At the end of the day, they have set themselves up with a lot of chances at a very solid base of players. People can suggest that you could do the same thing buying FAs but does that really work any better? The yankees have spent how many countless millions of dollars to be a whole 2 games up on the Royals. Perhaps you can make the argument that the Yankees can retool quicker via FA than the Royals who languished in mediocrity for years but that also assumes a level playing field in terms of money. And if the Tanaka situation shows us anything, even if the cubs outbid 28 other teams if the Yankees want a player they have deeper pockets. And if you need one specific player in FA to win and the Yankees want him you're screwed. As such, building largely via FA is a fools errand.
