I see your point and the next few years will show us if they get on the level of the Bumgarner Giants or just another one time WS winner. It really depends on how their pitching holds up. If Lester and Darvish can keep it going, and if Q can go back to his South Side form. But winning the one WS with the Cubs is enough for Theos legacy there, just given the history.
The other thing is we hype up these franchises and rebuilds and prospects so much now, most of them have to fail.on some level. Between the Astros, Cubs, Braves, Yankees, and White Sox, 10 of the next 6 World Series are already spoken for. And that doesn't count the high payroll Red Sox, Nationals, Dodgers, etc, nor other fluky teams that get hot in the postseason and play spoiler.