Besides the drought that some never saw ending in their lifetimes, the World Series ring that the Cubs won means so much more for Cubs fans. Of course game 7 had to end in a much more dramatic way than most Cubs fans would have preferred, but the history of bad luck that has clouded the franchise made it appropriate that the Cubs won a ring with the Indians having the winning run at the plate.
To anyone who thought the Cubs won a ring out of pure luck, you're dead wrong. Building a winning team does not come from signing 2-3 big name free agents and having mediocre players surrounding the superstars thinking that would be enough. Building a winning team starts with building a farm system that previous Cubs regimes neglected to construct. Plus, the beauty of where the entire organization is in is that when the team needs to make a trade for a big name pitcher or any other position mid-season, they can get rid of a couple of prospects without mortgaging the future, very few teams can say that.
A few trades that the team made in previous years seemed to be somewhat of an afterthought at the time, but with Jake Arrieta and Kyle Hendricks, team scouts saw that something special was coming. Patience was emphasized to fans and the patience was worth it.
Many believe the idea of how home field advantage is determined in the world series is not a great idea but not having home field advantage actually benefited the Cubs. The intense hype in and around Wrigley Field played against the Cubs and playing the last two games away took some pressure off them.
Tom Ricketts spoke with Bob Nightengale about the status of being called "the lovable losers," It was just so important for this organization, to put this lovable loser crap to bed. Despite all of the successes of the year, had that game gotten away from us, the next morning’s stories were going to be all about the Cubs losing again. ... That's why it's so important to get this behind us. We had to get past that and put that in the history of the Cubs, and not the future. We changed that dialogue, and now, it's all a thing in the past."
The drought did play into the heads and minds of previous Cub teams, but as Bryant told Ken Rosenthal after clinching the NL pennant, unlucky history did not raddle the 2016 team, and that was one of the biggest reasons why the Cubs were able to win it all. There was a significant point in all 3 series in which fans had some doubt about the team's chances, but if there was one word to describe the 2016 Cubs team, it would be resilient. Add to that the team is very young and it would have been easy to let the youth of the team get the best of them, but the entire team bought into Joe Maddon's philosophy of "embrace the target."