Top three reasons the Chicago Cubs have seen their window start to close

Mere years ago, we salivated at what we believed to lie ahead. Now, the Chicago Cubs are once again searching for answers when it comes to what went wrong.

First, let me begin by saying. It’s no guarantee the Chicago Cubs are on the downhill. But it is clear the clock is ticking and what we recently thought could be a dynasty is standing on a mountain of unrealized potential after back-to-back disappointing seasons.

The end of the 2018 campaign still came on the heels of 95 regular season wins. Granted, the season ended in a flurry – with the rival Milwaukee Brewers coming to Wrigley Field and winning a winner-take-all Game 163 to claim the National League Division crown – and the Cubs subsequently losing in the NL Wild Card game, but 95 wins is nothing to sneeze at.

This year, though, was an entirely different story in what proved to be Joe Maddon‘s swan song as Cubs manager. Chicago never finished a month more than four games over .500 and a late-season collapse, marked by a 11-16 month of September, put the coffin in the team’s hopes of an unprecedented fifth straight postseason appearance.

There’s plenty of blame to go around. Maddon already paid the price. Chicago opted to not give him a new deal at season’s end, officially marking a looming changing-of-the-guard. The three-time Manager of the Year may not have done enough to lose his job, but he certainly didn’t do enough to keep it, either.

But when you look at what happened since the team’s historic 2016 World Series run – Maddon is the least of the worries. A self-made reckoning is coming for the Chicago Cubs and it’s up to Theo Epstein and the rest of the organization to respond.

Chicago Cubs: Too much faith in the team’s young core

When you win your first World Series in over a century, it only makes sense that no matter who you are – Maddon, Epstein or a fan like myself, you’re likely to be a little too emotionally connected to the group of players who brought it all home.

“Looking back at this group that we won with,” Epstein told the The Athletic (subscription required) at his end-of-year presser. “I had this belief that this group of players who won the World Series, many of them at 22 and 23 years old, were going to grow into an unstoppable set of players if we could continue to supplement them and show faith in them.

I can’t say Epstein was wrong to have such belief – at least not initially. Kris Bryant followed up his Rookie of the Year campaign in 2015 by winning the National League MVP. Kyle Schwarber recovered from what was believed to be a season-ending knee injury to return in the World Series and casually bat .412 with a .971 OPS. That seems pretty hype-worthy to me.

Anthony Rizzo turned in another remarkable campaign – leading the offense and playing Gold Glove-caliber defense at first. Javier Baez earned co-NLCS MVP honors alongside workhorse Jon Lester and even Addison Russell turned in the best numbers of his career, driving in 96 runs.

Since then, though, things have trended in the wrong direction. Bryant has battled injuries, Russell has fallen out of favor for reasons both on and off the field and age has caught up with the starting rotation in a big way.

“That (the core becoming an unstoppable force) hasn’t happened, and I’ve made decisions to pour a lot of resources — every available dollar — we’ve poured back into plugging holes in this group, trying to find pitching for this group, trying to elevate this group. We’ve traded a lot of prospects, a lot of young players who were blocked by members of this group. We’ve traded out of belief in this group.

Epstein’s steadfast faith in his young players now has the Cubs sitting at home in October for the first time since 2014 after the sporadic offense failed to deliver once again. As frustrating as the offensive performance has been from some of these guys, the organization’s failure to develop pitching looms even larger.

Chicago Cubs: Lack of homegrown arms is a glaring issue

Before we delve into this area of focus – let me say: if you don’t subscribe to The Athletic, you should. It’s worth every penny. Sahadev Sharma and Patrick Mooney penned a piece (which actually inspired this column) entitled, “Winner’s trap: How did a Cubs dynasty start to fall apart before it truly began?”

The entire piece is masterfully constructed and dives into things on a much deeper level than I do here. Take the time to read it, really – you won’t regret it. One thing jumped out at me though more than anything else.

Through eight draft classes, the Epstein regime has selected 124 pitchers who signed with the organization. Only seven – Paul Blackburn, Duane Underwood Jr., Pierce Johnson, Zack Godley, Rob Zastryzny, James Norwood and Dylan Cease – have made it to the big leagues with any team. So far, only Godley (2.9) has accumulated more than 0.3 WAR in his career.

This – more than any other issue this organization faces – represents an obstacle that cannot be overcome in the near future. You can’t simply start drafting and developing pitchers more effectively. It takes time, money and a willingness to look in the mirror and question the practices and policies you have in place – something Epstein now seems more willing to do given the outcome of the 2019 campaign.

For much of the Epstein era, the front office has focused its draft strategy around high-impact position players. We’ve seen it work pretty well time and time again, with the likes of Bryant, Schwarber, Ian Happ and, most recently, Nico Hoerner, showcase their skills at the big league level.

But when it comes to arms, it’s been a different story. Last winter, the Cubs were forced to shed payroll and bring back Cole Hamels at $20 million to round out their rotation. This piecemeal approach to building a pitching staff – one that is looking older and more inconsistent than ever – isn’t a recipe for sustained success.