Reflections on a crushing disappointment of a Cubs season

Every year, I write one of these: My personal thoughts, feelings and reflections on the Cubs baseball season just completed.

Over the past four years, they’ve been written on the cusp of the Cubs entering postseason play. As recently as two weeks ago, we all thought they’d be heading that way again, at least as a wild card, perhaps as division champions. I certainly did not expect to be posting “this season’s done” reflections before September even ended.

The nine-game losing streak that ended the four-year postseason run was stunning in every way. It’s not my purpose here to rehash that streak; we all lived it, we all saw what happened, we all know how it made us feel. Imagine how the players feel now that they’re heading home for the winter. And if you think they don’t care, you’re wrong. One thing Joe Maddon did as part of his five years here is change the culture of the ballclub to expect to win. “No more loveable losers,” said Joe, even if not in those precise words, and it happened. The Cubs won the World Series. We can only hope that culture of winning remains now that Joe is gone.

Had they not won in 2016, the collapse of 2019 would have rivaled the one 50 years ago, in 1969. That team expected to win, until they didn’t, and the reverberations from that year’s debacle resonated for decades. Back then, it was because they hadn’t won a World Series in 61 years back then, or even been in one for 24. Those numbers increased, and increased, and increased... until at last, we all experienced the joy of victory. Four years ago, no living Cubs fan knew how it felt to win the ultimate prize. Now we all do.

That doesn’t make this year hurt any less, but it does temper it a bit. Last November I asked you all, “Is one World Series championship enough for you?” 28 percent — more than a quarter of you — said yes, you’d be good with that. That’s obviously nowhere near a majority, but it’s a significant minority. Remember the “Just one before I die?” T-shirts? A lot of us felt that way. Now there’s a “Just two before I die” shirt, and every Cubs fan surely wants the Cubs to win again, and again after that if possible.

Therein lies the difference between us now, and us then. With the 108-year drought, Cubs fans were different from fans of any of the other teams who had won in that span, even Red Sox and White Sox fans, who had long droughts not quite that lengthy before they won in 2004 and 2005, respectively. But now? We’re just like any other team’s fans, desiring to feel that 2016 feeling all over again.

I believe it’ll happen. Some people call Tom Ricketts “cheap,” but that is emphatically not the case. The Cubs had the highest payroll in team history in 2019, second only to the Red Sox, and likely will have the same in 2020. The issue isn’t spending, but spending wisely.

And that’s where I come to the efforts of Theo Epstein & Co. Pull up a chair, this is gonna be long.

Theo put together the team that won the 2016 World Series. For that, he gets a great deal of acclaim along with applause, appreciation and accolades, and between that and ending the Red Sox drought, probably a ticket to Hall of Fame induction someday.

But we were promised “waves and waves” of talent. That hasn’t happened. If Theo wants to know what went wrong with the 2019 Cubs, the first thing he ought to do is look in the mirror.

Theo’s drafts have produced middling results at best. Of the four key No. 1 draft picks this front office made from 2012-15, what do the Cubs now have?

• One All-Star level player (Kris Bryant)
• One player who finally came into his own in 2019 (Kyle Schwarber)
• One defensive-minded player who had an awful 2019 and who now is probably no more than a fourth outfielder, if that (Albert Almora Jr.)
• One player whose future is still up in the air and who spent four months in the minors in 2019 (Ian Happ)

To me, that’s not a stellar record, not for No. 1 picks, anyway. Further, there are exactly two other position players on the current 40-man roster who were drafted and developed by this front office: David Bote, who was the team’s 18th-round pick in 2012, and Nico Hoerner, the No. 1 pick from 2018 who surely looks like a keeper.

Two key players on this team, Javier Baez and Willson Contreras, are holdovers from the Jim Hendry regime. There are three pitchers on the 40-man roster who were drafted (or signed by) and developed by the current front office: Adbert Alzolay (international signing, 2013), James Norwood (seventh round, 2014) and Duane Underwood Jr. (second round, 2012). One other 40-man roster player, draftee Justin Steele (fifth round, 2014), has yet to play in the big leagues. Dillon Maples, who still has promise, was another Hendry draftee.

It’s true that some players from the system were traded in major-league deals, and that is another worthy use for prospects. Gleyber Torres, Eloy Jimenez and Dylan Cease are probably the biggest names sent away in deals. Torres is an All-Star, but I don’t care because that deal helped the Cubs get their ring. The jury’s still out on Jimenez and Cease, although the return on that trade, Jose Quintana, has been so-so at best.

All of this, though, is an indictment of the amateur scouting and player development staff, and likely one reason Jason McLeod was “promoted” (read: “kicked upstairs”) a few weeks ago. The team has not developed “waves and waves” of position players, and has not developed starting pitching at all. This has to change.

Compare that to the Cardinals: On their 40-man roster (or 60-day injured list) are 17 players who were drafted or signed originally by their organization, including key parts Yadier Molina, Kolten Wong, Michael Wacha, Dakota Hudson, Jack Flaherty, Tommy Edman, Matt Carpenter, Paul DeJong and Harrison Bader.

Theo & Co. told us they’d do something like that when they came to the Cubs eight years ago. It hasn’t happened. Theo needs to do some reflecting on why that’s the case and take steps immediately to fix it.

Lest you think I’m simply bashing this front office, let me say that many of the free-agent signings and trades made by Theo have worked out spectacularly well. The acquisition of Jake Arrieta and Pedro Strop for Scott Feldman and Steve Clevenger was one of the best trades in Cubs franchise history. Outstanding value was brought to the North Side in the trade of Ryan Dempster for Kyle Hendricks, as well as the deal that brought Dexter Fowler to the Cubs for Dan Straily and Luis Valbuena. And acquiring Anthony Rizzo for Andrew Cashner not only produced great results on the field, but got the Cubs a beloved player who is a franchise icon.

Other trades, including shipping away DJ LeMahieu for Ian Stewart and trading Tommy La Stella for a bag of magic beans, did not work out at all.

Here are all the various deals Theo & Co. made in building the 2016 World Series winner. Generally, the results up to then were very good. Since then? Not so much.

The signing of Jon Lester as a free agent was one of the best, if not the best, in Cubs history (despite Lester’s poor 2019). I’ll note that I don’t think Lester comes to the Cubs if Joe Maddon hadn’t been hired as Cubs manager in October 2014. The Maddon hire was the sign to everyone that the Cubs were serious about winning right now. If Maddon’s not Cubs manager for 2015, I think Lester signs with the Giants, who offered him more money and sent Buster Posey to Lester’s Atlanta-area home to say, “I want to be your catcher for the next six years.” (Yes, that actually happened.)

The signing of Ben Zobrist was also great for the Cubs, getting the team a solid clubhouse presence who had just been on a World Series winner and had a long history with Maddon. Even though Zobrist will turn 39 in 2020 and has somewhat diminished skills, I hope the Cubs will invite him back for one more year given his leadership qualities. They’ll be needed in a clubhouse that will have many different faces in 2020.

The signing of Jason Heyward is a mixed bag. His batting production isn’t what the Cubs thought they were getting, except for a few flashes in 2019, but his defense was largely solid and then there’s that little rain-delay speech he made in 2016. You might not think that mattered, but I do, and I think his teammates did. He’s been basically a 2 bWAR player for the Cubs, good, but not for the amount of money they’re paying him.

Many of the rest of Theo’s free-agent signings have not worked out well, and in fact the signings of Tyler Chatwood and Brandon Morrow hamstrung the front office to a certain extent over the last two years, because those players tied up money that could have been used for help elsewhere. Chatwood redeemed himself somewhat in 2019 and could be a useful part of the pitching staff in 2020. For less money than the Cubs paid Chatwood, they could have had Miles Mikolas — and reportedly they were interested — and that might have produced better results in both 2018 and 2019.

This failure to acquire meaningful talent got much worse this year. Granted, Theo was working on a budget that simply would not go above the luxury tax ceiling — and we can argue all we want about that, but it was a fait accompli — all Theo added to the 2019 roster was Daniel Descalso (a complete and utter disaster) and relievers Brad Brach, Xavier Cedeno, Tony Barnette and Tim Collins, none of whom were of any use. The Craig Kimbrel signing was something everyone here wanted, and it appeared to be the right thing to do, but that, too, turned into the proverbial pumpkin.

Before the season, Theo Epstein said he thought it was worth giving the current core group of Cubs another shot at a World Series. I agreed at the time. But there were enough holes and flaws on the 2019 Cubs to make that not happen. It couldn’t have helped that Joe Maddon had constant churn in his coaching staff after 2017, and it appears much of that was not his choice. Joe also seemed different after Dave Martinez departed to manage the Nationals. You’d often see Maddon and Martinez together in the dugout discussing the game, strategy, etc. That never happened with bench coaches Brandon Hyde and Mark Loretta. I don’t think I ever saw Maddon and Loretta together during a game in 2019, not once. You might not think that matters; I do. Will this coaching staff return under the new manager in 2020? Or will this group of players have yet another pitching coach and hitting coach? This turnover cannot possibly help matters, although this article hints that Theo isn’t happy with the current staff:

The Cubs coaches are expected to learn their fate Tuesday, and a source said Epstein expressed his displeasure with players’ repeated mistakes during a stern meeting with the staff last month.

So while this management team brought the World Series title here and we’ll all be eternally grateful, right now I’m in “what have you done for us lately” mode. With two years left on his deal and the possibility that he moves on after 2021, Theo Epstein has a lot of work to do in order to get a contending team back on the field in 2020. That’s important not only because the Cubs now — thanks in no small measure to Joe Maddon — now are expecting to win every year. That’s a good thing, but if they don’t, they will have trouble selling the new Marquee Network to cable and satellite operators. Will the big money that’s been assumed to be coming actually come? This comment gives me pause:

“The new TV deal, at least for the first few years, basically means the exact same thing for us as the old deal,” Epstein said this week in Pittsburgh. “The first few years will basically replicate the old deal, and then with potential for real growth down the line.”

So... maybe that big money isn’t going to be there right away? What does that do to Theo trying to put together a winner in 2020?

It appears that the parting between Theo and Joe was amicable and they both simply agreed that it was time to move on. I can accept that, but the new guy, whoever he is, will have big shoes to fill. Joe Maddon will always be remembered as the guy who finally got this team over the hump we never thought would be scaled. They ought to build a statue in his honor. We will always, ALWAYS have this. [VIDEO]

In the meantime, Theo & Co. have work to do. There is still a lot of talent on this team and a nine-game losing streak at the worst possible time doesn’t change that. Theo’s Red Sox missed the playoffs in 2006, two years after winning the World Series. The next year, they were 96-game winners and won it all.

It can happen here. Don’t let the September collapse get you too down. There is always next year, as Cubs fans have known for decades. Even with that, though, with Maddon’s departure, core players perhaps being traded, and WGN-TV and the Cubs parting ways and the Marquee Network set to premiere next year, it really does feel like the end of an era.

But I can’t wait for 2020. How about you?

Tomorrow: My final 2019 season grades for Cubs players