Spending a ton of money hardly ever equates to wins. So although spending for proven talent theoretically gives you a higher chance, it comes down to chemistry, coaching, and a little bit of luck to win a World Series.
This concept was proven with the Dodgers last season who clearly looked like the best team in baseball. Of course, that all came crashing down in crunch time due to question marks in their pitching unit and not being able to score runs when it mattered most.
Paying top dollar is never an easy choice with years of turmoil hanging in the balance.