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The next few steps for the Cubs could be awkward

Theo & Co. are going to have tough choices to make this offseason.

Photo by Nuccio DiNuzzo/Getty Images

It wasn’t supposed to be like this, many thought. After the 2016 World Series title, the division titles and trophies were supposed to be willingly surrendered. The waves and waves of talent would be regularly contributing to the success. Alas, that isn’t especially happening. After this weekend against the Nationals, it’s very possible that the changes this off-season might be more than cosmetic. It could get somewhat awkward watching the Cubs offseason transactions.

What seems to have happened was, the Astros, Dodgers, Braves, and a few others didn’t have an all-consuming obsession about the trading deadline in 2016. The Cubs won their title, and the Astros saved their pieces for Gerrit Cole and Zack Greinke. The Dodgers tossed a few to Baltimore for Manny Machado. The teams that have been rather good at generally developing talent are still doing that, and the Cubs are lagging.

Tossing aside any of the numerous debatable points, the Cubs are where they are, now. The Cubs really do appear to be a C+/B- team, as opposed to anything more elite. This season, they might or might not be better than the Cardinals or Brewers. For far to many, the premise of post-season randomness is the direct route to post-season success, not relying on an extended season of excellence. The 2019/2020 off-season ought to be interesting, but not for the reason last offseason was supposed to be (Bryce Harper or Manny Machado). The Cubs are in danger of rolling back to being “just another team,” because the next layer of talent hasn’t arrived.

The Cubs have very few players that can bring back significant returns in trade. About all that I would see are Willson Contreras, Kris Bryant, and Javier Baez. Trading Kyle Schwarber or Albert Almora Jr. are moves unlikely to move the needle. If “staying under” is the goal, it would seem that any of the above three that don’t sign an extension this off-season, their time in Wrigley would seem short. Whether we want finances against a limit to matter, they seem to. Any money coming off the books will promptly be spent on someone else, thereby further limiting the ability to add talent toward the deadline for mostly money.

In 2011 and 2012, the Cubs dove into a rebuild because they were no better than the fourth-best team in the division. They aren’t there now, and shouldn’t be in November, but they no longer appear remotely elite. Their roster is top-heavy, with few MLB-ready pieces for next season. Unless something starts to percolate from a “player development” perspective with the big club this next month, Theo Epstein may need to examine re-trading Nomar Garciaparra, as opposed to sweating over whether Joe Maddon (who I like) stays, or any of a few other “moving the deck furniture on the Titanic” adjustments this offseason.

Who would go, and what the return would be? It would be fascinating. It would be very awkward. Is there a front office that has an all-consuming obsession about winning a title the next two seasons?