After starting from a level playing field on Opening Day, there are always certain teams who find themselves falling lower and lower in the standings as a given season goes on. Though it can vary from year to year, with teams having an off season compared to their normal standards, for the last several seasons it has been two main teams: the Cubs and the Astros. 
Currently sitting dead last in their respective divisions through a fourth of the season played, and with no signs that things will be changing in the near future, even with a good amount of the season left to go, it’s once again not looking too good for either the Cubs or the Astros. However, despite neither having finished with a winning record since 2009, their fortunes could be changing over the coming years. One thing they both have in common is their strong farm systems, which are loaded with top prospects that will be coming up to help out down the road.
For the Cubs, having not reached the postseason since 2008, they currently have prospects such as Javier Baez, who’s off to a rough start to 2014 after dominating last year; Kris Bryant, who’s expected to have 40 home run power in the majors; and Albert Almora, who is a few years away but is likely to have a big impact once he reaches Chicago. Those players, combined with those they have now, should make for a good team beginning around 2016 and continuing for the many years beyond.
To go along with their already decent major league team, the Astros, who haven’t made the postseason since 2005, have a ton of talent coming their way, including Carlos Correa, who is expected to be an all around fantastic player; Mark Appel, who’s likely to get a late season call up if he’s performing well; and Jonathan Singleton, who possesses some above average power. After losing over 100 games and being the worst team in baseball as of late, the Astros could see things turning around very soon.
The only good thing about performing so poorly each season is that you receive a high pick in the following year’s draft, with it looking likely that the Astros will take Carlos Rodon as the number one overall pick in the upcoming 2014 draft (the Cubs have the fourth overall pick.) But even so, your top picks in the draft, which subsequently become your top prospects, don’t always pan out and reach the big league level. And even when they do, for some players, it takes them a bit of time to adjust once they get the call up.
The most recent example of that being George Springer, who has hit a mere .222 with 3 home runs so far this season with the Astros after blasting 37 homers to go along with a .303 batting average as part of their farm system in 2013. Though he’s predicted to still have a great career, sometimes it just takes awhile for players to make the adjustment to big league pitching, no matter how good they are.
And therefore, while I’m not saying either the Astros or the Cubs will be winning the World Series in the coming years, I do feel that with their high level of talent from the minors on its way they will become much more competitive than they currently are, having to settle with last place finishes year after year.
With it being nearly equal in terms of current talent, and taking prospect depth into consideration, it’s somewhat difficult to predict which of the teams will be the best half a decade from now. But if I had to choose, I’d likely go with the Cubs, even though the Astros should be a lot better as well. It’s truly too close to call, and that’s something to look forward to if you’re a fan of either team — or just a baseball fan in general.
Who do you think will be the better team in five years?
The Unbiased MLB Fan 
They both have good farm systems; the Lastros are top-heavy and the Cubs are deep, but I can say with pretty good certainty that the Cubs win out on the farm system side. Then again, they have a long history of poor player development and busts. Then again again, that was the previous administration. The Lastros haven’t had much talent coming out of their farm system either, but instead of has-beens they’ve stocked up on never was.
I’d say Cubs for now, but it’s pointless to project turrible baseball teams that rely on player development and prospects. At various times in the last decade, we thought the Royals would surely be a 100-win team by now with all the talent they drafted.
A lot of your points make sense. It should be interesting to see how they both turn out in a few years.
I work for a the Mariners’ AA team, and got the opportunity to see the Cubs AA team in person, and I was extremely impressed. Bryant and Soler are studs, but they also have a really talented supporting cast around them. When the series ended, I even got to meet Bryant and Soler, which was very cool. Even though I’m a Cardinals fan, I know we’ll have some company at the top of the NL Central in a few years.
http://stathead.mlblogs.com/
Bryant and Soler are certainly some of the key pieces of their farm system, but I agree, they do have a god deal of good players besides them. I could easily see the Cubs being competitive within a few years, as you said.