How does one measure success in baseball?
Championships.
The SF Giants have won three World Series in five years. Some skeptics claim that the Giants were not "the best" team, wild card berths, etc. The bottom line is still the rings.
Victories.
Any team can boast about having a winning season. For some clubs, being over .500 is a "moral victory." It is enough to keep a team's fan base in excitement and expectation mode to continue to be a competitive team. It is enough to sell improvement if you are competitive series to series.
Individual Awards.
This is a participation trophy in the arena of team sports. Individual accomplishments are fine, so long as they support the ultimate fan goal: championships. A batting title champ or a Cy Young award winner are great, but it does not mean a deep play off run - - - the bitter taste in Detroit is the latest example.
So how do we measure Theo Epstein's first three years at the helm?
In the last three years, the Cubs have lost 286 games. That is an average of 95.33 losses per season.
It is nice to have respected drafts, and publications liking your revamped minor league system, but none of that really matters (it is all speculation) until you can get victories at the major league level.
