Chicago Cubs: What if the Cubs don’t win another World Series with this group?

When the Chicago Cubs finally broke through as one of the top teams in the league, many believed they were on their way to becoming baseball’s next dynasty. But what if that doesn’t happen?

In December of 2014, the Chicago Cubs signed ace left-hander Jon Lester, who at the time was the top free agent starting pitcher on the market. This was really the first moment that made fans realize the days of finishing in last place year after year might finally be coming to an end.

For years up until this point, North Siders had gotten used to seeing what few assets the team had being shipped away to the contenders of the league. But the Lester signing signified that the Cubs were on their way to being contenders, too. And it didn’t take long. Competing a year ahead of schedule, the Cubs won 97 games in 2015.

In 2016, they finally pulled it off. After more than a century-long drought, the Cubs had won the World Series. When Theo Epstein took over as President of Baseball Operations in 2011, he was blunt about the fact that fans would have to be patient to see future success. But his plan worked. In 2014, Chicago won just 73 games. Two years later they won in it all.

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Championship window is still open

Epstein’s plan from the beginning was to stock up on young position players. And that’s what the team did. With trades and high draft picks, the Cubs assembled a talented group of young hitters. This set them up to be competitive for years to come.

So far they’ve been exactly what some expected: a powerhouse. They’ve now been to the postseason three years in a row while winning the NL Central in two consecutive years. And once again, they appear to be the favorites to win their division.

They’ve still got one of the best lineups in all of baseball, along with a stellar defense. So the championship window is still wide open. But what if they don’t win another World Series? What if, after all the talks of becoming the league’s next great dynasty, they fizzle out without another World Series trophy to show for?

In short, that would be a bit of a disappointment. Plenty of teams have shown a willingness to go all-in for a short window of opportunity to win a championship. But that’s not the case for this Cubs team. This team was built to stay in the mix for a long time.

It might be painful to see all the team’s best prospects being traded away, but that’s what happens when you’re a perennial contender. For the Cubs, now isn’t the time to be stockpiling prospects. And now isn’t the time to be saving money. Championship windows don’t last forever. So when you have one, you do everything you can to go on the best run possible.

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Do whatever it takes

Winning the World Series is no easy feat. Fans should no doubt be satisfied with a 2016 World Series victory. But it’s okay to want more. Because the opportunity to win more is still there. Players like Kris Bryant come around once in a generation. The last thing they want to do is wallow in mediocrity during his prime.

There’s no indication that that’s about to happen. But the Cubs should be doing everything they can to make sure they’re as competitive as possible while their star players are in their prime years.