I'm 42. I distinctly remember when what you might call the modern free agent era began in the late-80s after the collusion cases were ruled against the owners. (People forget that Andre Dawson actually had to take a pay CUT! when he signed to play with the Cubs.) The Cubs had a young team make the playoffs in 1989 and everyone thought the best was yet to come. The 90 team had a few guys not able to repeat their breakout years, and Sutcliffe got hurt, but the young core was still there. So in '91, they pushed their chips to the center of the table and went on the first free agent splurge in Cubs history. They signed '87 AL MVP George Bell, '88 AL Cy Young runner-up Danny Jackson, and two-time All Star closer ('86 and '90) Dave Smith.
Of course, Jackson and Smith were awful. Actually, pretty much all the starting pitchers other than Greg Maddux were awful. And a real bad pitching staff spoiled the season for a pretty darn good offense. Didn't help that Zimmer was fighting with the front office and got canned less than 40 games into the season when they were a game below .500.
The next time the Cubs pushed all their chips to the middle of the table was 2004. I think we all remember how that went. Possibly the least likable team with a winning record I've ever tried to be a fan of. They were quite obviously sick of each other by the time the season ended.
And then 2008. A great team that just ran into a buzzsaw in the post season. Main difference between 2008 and 2015 is that was an old team whose window was rapidly closing, whereas 2015 was a young team that looks like it has at least a good 5-year window left to it.
So anyway, I'd say this is the fourth time in my life that the Cubs have really made a serious push to win it all. This one feels different though for a number of reasons. It feels sustainable. It feels like it's part of a long-term plan. It doesn't feel like a bunch of baseball cards clodged together to make a team.
I hope I'm right.