Five reasons the Chicago Cubs never became a dynasty

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The Cubs were supposed to become a dynasty … but that never came to be.

Funny things happen on the way to where you think you’re going. One day, everything is perfect and going your way, and the next… well, life tends to throw you lemons, sometime even pelting you right in the head.

For the Chicago Cubs, all seemed right in the world after the 2016 season. They had the perfect manager, an unparalleled core of youngsters, a veteran rotation and ownership willing to spend money on the field for talent and on the stadium (and surroundings) itself.

Most Cubs fans would tell you that breaking the curse and winning in 2016 was enough, and surely, it was a fabulous feeling and cathartic experience for many. Yet, when true fans are honest with themselves, there’s no way they saw the next four years going the way they did. While it’s tough to be disappointed with 90+ win seasons and trips to the postseason in all but one year during this “window of contention,” I’m sure that frustration and disappointment are exactly the feelings most folks hold looking back. And now, it seems that at least part of that core will not be around and maybe more will be joining Kyle Schwarber elsewhere before the offseason is over.

So, without further ado, here are the five reasons the Cubs never achieved that coveted dynasty status despite all the potential and ability to get there.

Chicago Cubs: Addison Russell… what a waste.

When the Cubs traded then-ace Jeff Samardzija and another quality starter, Jason Hammel, to the Athletics for Addison Russell, Billy McKinney, and Dan Straily in July 4, 2014, some Cubs fans were a little annoyed. A year later, no one was really upset. Two years later, the talk was about how badly Theo Epstein had fleeced Billy Beane for one of the best all-around shortstops the game would know for the next decade.

Fast forward another year and some warts began to show. Injuries slowed him. Then, things just started falling apart and unravelling in his personal life. And, of course, this had a profound effect on not just him, but the entire club, as it all played out like a bad nightmare. Child support payments paid in quarters, stalking, abuse. Russell was disciplined by both the Cubs and MLB, but given a second chance with the club; that is, of course, until his play couldn’t even attempt to support his abominable personal behavior.

Russell helped the Cubs win the 2016 World Series with one of the best defensive squads in baseball and teamed with then second baseman Javier Baez to form the best middle infields in all of baseball. That much no one will be able to take away. However, his personal and professional setbacks and poor performance will be a huge “what if” in both his life and the course of the Chicago Cubs franchise.

Losing a 23-year-old franchise shortstop isn’t just something you usually make up for, although the Cubs did make the best of it by sliding the even more talented Baez into his spot. Still, they got nothing out of or for Russell before his prime even began.

What could have been, no one knows, but the scary thing is that Russell is still only 26 years old.

(Photo by Jonathan Daniel/Getty Images) /

Chicago Cubs: The perfect guy for the job… until he wasn’t

Joe Maddon was the best manager the Cubs could have hired in 2015 and he was the best man for the job as he guided the team to the 2016 World Series. I don’t want to say that no one else would have been able to do it, but his ability to coax the most out of his players, especially soon-to-be stars like Willson Contreras and Baez, was second to none.

His ability to keep his players loose was unmatched. His ability to let the players do their own policing was all for the best with veterans like David Ross, Jon Lester, Miguel Montero, Jake Arrieta and John Lackey around the clubhouse.

He connected with the youngsters and let everyone be the best version of themselves. He impressed upon the team a few simple rules, but didn’t constrain or tyrannically oppress anyone. As noted, he was the perfect man for the job when the Cubs window of contention began.

Unfortunately something happened along the way and impediments sprung up. Whether those obstacles were with ownership, the front office, or talented young players not progressing as expected, we’ll probably never know for sure, but things weren’t working by the time 2018 and 2019 rolled around.

There’s also the matter of so many hitting and pitching coaches to go along with really successful teams, so that’s also a bit of a mystery. That being said, while I wasn’t a fan of letting Maddon go, it seems in hindsight that maybe the Cubs hung onto him too long.

Chicago Cubs: The plan worked, but then stalled

From the start, Theo Epstein’s plan was to buy pitching and draft elite hitters. Albert Almora, Kris Bryant, Kyle Schwarber, Ian Happ, Nico Hoerner. Every first-round hitter Epstein has drafted (other than 2020 Ed Howard) has already made it to the bigs and had an impact (even if some have stalled, been inconsistent, or fallen off since). In fact, every single one of them had immediate impacts upon hitting the big stage. The first three were key cogs in the ’16 World Series. Happ and Hoerner may be cornerstones for the franchise for the next decade.

Part A of the plan went pretty much to plan. Part B was to buy or acquire pitching. Kyle Hendricks, Jake Arrieta, Pedro Strop, Mike Montgomery, Carl Edwards Jr., Dan Haren, Aroldis Chapman, Alec Mills, Jose Quintana, and Wade Davis were all traded for. Check. Jon Lester, John Lackey, Yu Darvish – all signed to deals, with Lester’s and Darvish’s doozies.

Seems like everything went to plan. And, to be fair, it did in that the Cubs won a World Series directly because of that plan. The signing of Lester and trade for Chapman accentuate exactly what it takes to win sometimes – overpaying on the back end to get the elite front end of a top line starter and giving up a stud prospect in Gleyber Torres to get the guy who carried the pen into the World Series.

The problem was that during most of that time, not one Epstein-drafted pitcher made it to the bigs. Now, international signees Adbert Alzolay and Brailyn Marquez have finally made it and could be rotation pieces in the future, but the Cubs just haven’t been able to supplement the rotation with homegrown talent in the last couple years as the finances have dried up a bit. So, while the philosophy worked to get one trophy, it would seem it hindered adding multiple trophies.

Chicago Cubs: Bad Luck and maybe tough luck here…

First of all, anyone blaming the shortcomings or disappointment of the last few Cubs seasons on ownership not ponying up enough money just hasn’t been paying attention to the Cubs payroll the last six seasons. Sure, the Ricketts could have ponied up 300 or 400 million dollars for a bloated payroll that may not have won any more than what the Cubs did win, but it still wouldn’t have been enough for some fans if they didn’t win.

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The bottom line is that Chicago spent more than enough money to win. The problem is that the team became locked into large and long term deals that hamstrung the team and allowed almost no financial flexibility as the Cubs core got older and more expensive.

The goal was always to acquire pitching and draft hitters, and it mostly worked; yet, when some of those pitchers flamed out or suffered injuries, the money seemed tight. Jason Heyward’s contract was an overpay from the start. Yu Darvish, despite being one of the best pitchers in baseball the past year-and-a-half, struggled mightily due to injury his first year-and-a-half with the club.

Brandon Morrow, newly-signed to a minor league deal by the Dodgers, could never get out of his own way with injuries despite being dominating when healthy. Tyler Chatwood never panned out in the way that Theo Epstein had hoped. Heck, Craig Kimbrel was not good in 2019 or the first few games of 2020, despite turning it around after shaking off the rust in low-leverage spots. And don’t even get me going again on picking up Daniel Descalso immediately after shipping out Tommy La Stella for basically nothing.

By the way, I didn’t even mention anything about some of those trades…

(Photo by Gregory Shamus/Getty Images) /

Chicago Cubs: “You go, we go” never went when he left

The Cubs never found a leadoff hitter to replace Dexter Fowler.

Heck, the Cubs still haven’t found a leadoff man to replace him. While I’m not suggesting they made a mistake in letting Fowler walk and get handsomely paid by someone else for less than elite performance, they never addressed a hole that has been sinking the ship ever since.

When you have a Ferrari but can’t start the engine, what good is the car? When you have a super fast computer but no internet connection, what good is the computer? When you have a juggernaut of an offense and you can’t get it started, there’s a big problem. This is exactly the problem the Cubs have had the past four seasons.

Sure, they’ve tried to plug and play with Kyle Schwarber, Jason Heyward, Ben Zobrist, Ian Happ, and others. Problem is, they wrecked Schwarber for the better part of a season and then wrecked Heyward for a half season. Zobrist retired, and Happ still hasn’t played a full 162 game slate at the big league level.

When you’re an elite organization, you can’t allow a hole as gaping as the Cubs leadoff spot stay unplugged for four years. Yet, that’s exactly what has happened. And that hole has, in turn, temporized and seized the offense right off the throne in the National League.

Next. Top Five Kyle Schwarber moments. dark

While the Cubs could still find success in 2021 and beyond with many of the current players at the big league level and in the minors, the fact that Maddon, Epstein, and now Schwarber are gone pretty much signals the end to this window for the North Siders.

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Chicago Cubs: Five reasons the Cubs never became a dynasty