Looking at the Cubs, Yankees, Red Sox, and Dodgers. It is very interesting to see how more money has often times created more problems for these teams when they have chosen to simply buy players and not farm them.
The Cubs had always spent their money on pitching when they should have spent their money on hitting. But when they finally hit on a young crop of hitters, they were able to go out and spend money on improving their pitching with Lester and Chapman to push them over the top and win their first World Series since 1908.
I would even say that the Yankees paid a ridiculous price to only get 1 World Series Title while holding the contracts of A-Rod, Teixeira, and CC. Especially, how much money they were locked in for on the back ends of these contracts when the players dropped from their elite status.
Now the Dodgers have started to create something great with young players like Bellinger and Seager paired with the arms of Kershaw and newly acquired Yu Darvish. Bellinger, Seager, and Kershaw are players they did not spend top dollar to acquire but rather developed them and spent the money on them when they needed to. But with how good the Dodgers have been lately, I am going to bring up the skeletons in their closet and point out that they are still paying almost $125M in contracts for players who aren’t even playing for them any more! They have the money to spend so they’ll be fine, but when you look at what they could use that money for if they focused on development and managing their money instead of throwing money at all their problems, this team might look very different and might have actually had some true playoff success in the last 10 years.
The Yankees and the Dodgers are in a similar spot, where they are just about free from those anchors of contracts they are still paying out and will be able to pay it to talent they groomed themselves and balancing it with Darvish like players to compliment what they already have.
Before the Yankees got those big contracts, they still had a solid young base built around Jeter, Posada, Rivera, and Pettitte. With that young base they added players like Clemons to take them to the next level. But when that base got older, they still bought those players to take them to the next level like A-Rod and CC but avoided the truth that the base foundation was getting older and they needed to go back to developing that foundation with younger talent.
Daymond John, in the Power of Broke talks about the truth of what more money does is hide your problems from the world and those problems can only be hidden for so long. To be successful regardless of whether there is a salary cap in your league or not, you need to be scrappy and win at the draft table and be successful with a little before you go out and buy a lot.
Using these teams as examples, more money can help you get to the next level with buying talent to improve what you already have, but without a base and culture of talent that you create, there is no foundation and you won’t have long term success.