Which is essentially what you're doing with your baseless, nonsensical estimation that the Cubs pissing away money on this below-average free agency class would bring the team closer to a World Series championship. Let's pretend for a minute that we signed two of the top five free agents (let's use Greinke and Michael Bourn, for example). Imagine that we gave Greinke the same deal the Dodgers handed him (six-years at a horrific $147 million) and Bourn got a 'discounted' signing of four-years at $64 million.
How much closer is that $211 million getting us to a World Series? We still have a glaring weakness at third base, behind the plate, we have question marks at closer, no immediate future at either corner outfield spot unless Brett Jackson proves early on that his revamped swing is ready to handle major league pitching. All these signings would do would create buzz among fair-weather fans and give the media some bits to chomp at.... and then the Cubs would still slide into a third or fourth place finish in the Central. Building a team capable of winning takes time -- forget the whole sustainable roster and building a farm system. Getting players that come together and play well as a unit for 162 games takes several years. You simply won't solve all of a teams' problems in one off-season. It simply can't be done.
I'm getting the impression that you'd be much happier with how the Dodgers or Blue Jays' off-season went as opposed to the Cubs for the simple fact that they both took on a ridiculous amount of salary. How do you think their fans will feel if both teams miss the playoffs or get swept in the first round? All they'll have to show for it is a horrible payroll that locks them into a bunch of injury-riddled, over-the-hill players. We all understand that there's no guarantee with prospects, but you can say the same for signing a guy to a lengthy contract. He may never live up to the money you're giving him. So, again.... if signing one or two guys gets you no closer to a World Series, why should a team tie up their payroll when they could give themselves a better chance to compete for a longer period of time?