Likability.
Everyone wants to be liked by others.
It is human nature. Part of our collective behavior.
Even during the mostly dark days of Cub fandom (the 1960s, 1970s), Cubs fans still liked the players on their team.
The reason for that was a) there were players who were always upbeat (Ernie Banks); b) there were players who really showed they enjoyed the game (Ron Santo); c) there were quiet professionals who performed well (Billy Williams); d) there were players who were workmen like, blue collar types (Rick Reuschel); and e) players who took accountability for their mistakes and promised to do better (Fergie Jenkins).
It is easy to be loyal when the team that you root for is out there hustling, trying to do their best, not whining or making excuses, and accountable to their fans. You really can't fault a person who is doing his best.
So even when the Cubs had bad teams during those eras, the likability factor was still strong in the fan base. Some fans embraced the American connection to the underdog. The Cubs were underdogs for most of current fans childhoods.
Yes, times have changed. There is more money pouring through the gates. Players are no longer part-time professionals but multi-millionaires. Teams are more interested in their "brand" revenue than wins or losses.
During the Ricketts era, it is getting increasingly difficult to like the Cubs. The touted moves for new players have fallen fairly flat. There are no "exciting" players. There are a few fan favorites, like Darwin Barney, who hustle in the field, but are major flaws that would not make them starters on any other club. There is a growing rumbling of excuses and management snips especially by pitchers who have seen their staffs traded liked day old fish at the seaport market.
The Cubs players are pretty bland and non-descript. They have little personality. They play a boring brand of baseball (no emphasis on hit-n-run, steals, taking an extra base, spectacular defense, etc.). Some would say they have just been "going through the motions" for most of the past two seasons.
And the marketing campaign that new, young, fresh, exciting talent is "coming soon" is like a fading billboard in a corn field that said "coming soon: amusement park" to the local kids. It does not help the here and now.
Winning can bring back fans. But how a team wins is just as important for the stability of the team fan base. The Cubs currently have no direction in dealing with their fan base.