Chicago Cubs: While one cannot take away from what was done prior to 2016, there were plenty of moments where fate was just on the Cubs side
Assembling the core that won the 2016 World Series and made it to postseason five times from 2015-2020 took a lot of work. Scouting, developing and investing in the right assets takes a lot of brainpower on the front office side and effort on the players’ side. Like mentioned earlier though, a lot could have gone differently from when Epstein started the rebuild.
This goes beyond things like the Astros taking Mark Appel over Kris Bryant in the 2013 MLB Draft, the incredible finds of Jake Arrieta and Pedro Strop from Baltimore or Dexter Fowler returning in 2016, but just what happened on the field.
Having key farm pieces like Bryant, Kyle Schwarber, Javier Baez and Jorge Soler all come up around the same time (between late-2014 and mid-2015) and all contributing in the second half of a season and the postseason was a remarkable feat. Having a big group of prospects like that all hit (literally), when needed most, does not happen every day. Those four guys combined hit 12 home runs in the postseason in 2015. Again, while much of that is just credit to the players doing their thing, the chances of that all coming together at the same time was pretty remarkable. Prospects are prospects, and there are no guarantees.
Another huge factor in their success was the near-clear bill of healthy this team had. Schwarber’s knee injury in April 2016 was a big one, but for the rest of the core, they all stayed on the field. Anthony Rizzo played in 160 games in 2015 and 155 in 2016, while Bryant played in 151 games in 2015 (note he was held in Triple-A the first week or so) and 155 in his MVP 2016 season. Also worth mentioning most of the 2016 regulars outside catcher and left field (it was a mix for those positions) played in 125 games or more. Fowler missed a few weeks, but Rizzo, Bryant, Addison Russell, Ben Zobrist, Javier Baez, and Jason Heyward all played in at least 142 games that year.
The five main starting pitchers in 2016 (Jon Lester, Jake Arrieta, Kyle Hendricks, John Lackey, Jason Hammel), started at least 29 games or more. Health is one of those things that is really hard to control and things can happen any moment, so for them to stay healthy the way they did when they grew and molded together was so important.
In terms of something falling in the Cubs laps during the rebuild…Joe Maddon becoming available was pretty dang fortunate. His leaving Tampa Bay and the Cubs pouncing on him was key in their success. Say what you want about Maddon and how he managed in certain situations, but the great culture that was created within the organization absolutely was important to their success. Who knows what would have happened had Maddon not become available.
One could go into a much deeper dive of what all transpired in 2015-2016, but this can help paint a picture. The Cubs created a lot of their own luck, but sometimes you just need lightning to strike for it all to go right.