Cubs Facing a Tumultuous Offseason After Epic September Collapse

Now that the Chicago Cubs' fall from grace is complete, the only question is if the recovery effort will fall to an all-new cast of characters.

What's certain for now is there won't be any October baseball at Wrigley Field this year. Even before the Cubs wrapped up their eighth straight defeat in a 4-2 loss to the Pittsburgh Pirates on Wednesday, the Milwaukee Brewers eliminated them from playoff contention with their 9-2 rout of the Cincinnati Reds.

The Cubs have at least one good excuse for their September collapse. In a span of just a few weeks, the injury bug picked off shortstop Javier Baez (broken thumb), first baseman Anthony Rizzo (sprained ankle) and third baseman Kris Bryant (sprained ankle). Sans arguably their three best players, the only way for the Cubs to go was down.

Even still, it wasn't supposed to be like this for the North Siders.

The Cubs held first place in the National League Central as recently as August 22, which was befitting of a master plan that churned out four straight playoff appearances between 2015 and 2018 and a World Series championship 108 years in the making.

Indeed, said master plan was for a dynasty. Theo Epstein began drawing it up when he was hired as president of baseball operations in 2011. He got his ideal field general when Joe Maddon was brought aboard in 2014, and he's since had the pleasure of managing homegrown stars and costly hired guns.

But while the Cubs' 103 wins and World Series triumph in 2016 only seemed to be the start of their peak, it's actually been a slow, steady descent from there. The Cubs slipped to 92 wins in 2017, and 2018 ended with them fumbling their division lead and bowing out in the NL Wild Card Game. 

At least in the context of these failures, what's befallen the Cubs in 2019 is less of an out-of-nowhere tragedy and more of an obligatory next step in a logical progression.

Of course, the powers that be in the organization don't have to let this continue. And perhaps the safest bet in Major League Baseball right now is that they won't.

Nuccio DiNuzzo/Getty Images

The first question the Cubs must answer is who's even going to be in charge going forward.

Though Epstein's $50 million contract still has two years left on it, some are speculating that either he (per Alex Speier of the Boston Globe) or general manager Jed Hoyer (per MLB Network's Jon Heyman) will return to the Boston Red Sox, where they previously won titles in 2004 and 2007.

Even if Epstein and Hoyer stay to lead Chicago's front office, there will still be the matter of whether the organization wants Maddon back in the manager's chair. About this, the man himself is feeling positive.

"It's not just a one-sided decision," Maddon told Laurence Holmes of 670 The Score on Wednesday. "We'll make that over the next couple days and we'll move it on from there. But I'm very pragmatic. I'm very optimistic. And so I'll just leave it with that. I'm very optimistic right now."

But since Maddon isn't under contract beyond 2019, the Cubs are under no obligation to bring him back. In his own interview on 670 The Score, Heyman even went so far as to say: "At this point, I think we can all count on the fact that the Cubs will have a different manager next year."

Making the manager the fall guy for a disappointing year isn't always fair, but the Cubs have some cause to axe Maddon. According to Baseball Reference, they have the widest negative gap between their actual record and expected record (based on run differential) of any team in the National League.

Data courtesy of Baseball Reference

But for the most part, a manager is only as good as the talent at his disposal. This is where wins above replacement paints a rather damning picture of how Cubs players have been trending:

• 2016: 57.2 (1st in MLB)
• 2017: 42.2 (7th in MLB)
• 2018: 45.0 (8th in MLB)
• 2019: 40.5 (11th in MLB)

Out of the underlying causes of these diminishing returns, the most distressing is how the Cubs' self-cultivated core hasn't quite congealed as expected.

The best seasons of Rizzo (2014-2016) and Bryant (2015-2017) are several years in the past by now. Former top prospects Kyle Schwarber, Albert Almora and Ian Happ have 9.8 career WAR between them in parts of 12 combined seasons. Fellow former top prospect Addison Russell's once-rising star has faded by way of poor production and a suspension stemming from domestic violence allegations.

Looking for homegrown success stories on the mound? Don't bother. The Cubs haven't had any.

They also haven't had much luck with their big signings. Though they'd probably forgo a do-over on ace left-hander Jon Lester's six-year, $155 million contract, they might like to have back the $412 million spent on Jason Heyward, Yu Darvish, Tyler Chatwood, Craig Kimbrel and Brandon Morrow. 

To wit, Heyward has topped out at 2.2 WAR as a Cub. Darvish and Chatwood have put out 4.5 WAR in their two seasons in Chicago. Morrow made 35 appearances in 2018 before he was undone by injuries. Since coming aboard in June, Kimbrel has dealt with both his own injuries and a 6.53 ERA as a Cub.

Meanwhile, the Cubs' trades for Aroldis Chapman and Wade Davis in 2016 and Jose Quintana in 2017 cost them three players who've gone on to taste varying degrees of stardom for other teams: Gleyber Torres, Jorge Soler and Eloy Jimenez.

Nuccio DiNuzzo/Getty Images

If nothing else, the team's upcoming financial situation looks better than the one that led chairman Tom Ricketts to cry poor last winter. Cole Hamels' $20 million salary is just one of many financial commitments the Cubs will be freed from this winter. Between that and whatever cash they're due from their new TV network, they should have the means to be active on the winter's free-agent market.

But even if the Cubs spend to fix their immediate problems, their long-term future will still have a bleak outlook because of the state of their farm system. It has slowly but surely become one of the worst in baseball over the last few seasons.

If the Cubs want to add some young, controllable talent in the near future, they're going to have to trade for it. To this end, they could "at the very least listen" to offers for Bryant this winter, according to ESPN's Jeff Passan. If he's on the table, Baez, Contreras and Schwarber might be as well.

One thing the Cubs almost certainly won't do this offseason is blow the whole thing up and transition into a top-to-bottom rebuild. The last few years haven't gone according to plan, but they're still too good to shut their current contention window and pivot to opening a new one.

Otherwise, it's looking like an "anything goes" sort of offseason in Chicago. And between executives, coaches and players, plenty of people could indeed go.

Stats courtesy of Baseball Reference.