10 Items for Cubs to Cross Off September To-Do List

Ah, the dog days of August are over. Only 28 games are now left before the long regular-season mystery wraps up and pressure-filled playoff games begin.

Though the Cubs currently own the best record in the NL, much still needs to happen between now and the first Wild Card game on October 2. Here’s a rundown of the 10 most important items for the Cubs to check off their list in September.

1. TCB in the Standings

Job one remains taking care of business (TCB) by winning the NL Central. Next is locking up the best record in the National League. The big benefit of best record is less about securing home-field advantage in the first two playoff rounds and more about facing the winner of the Wild Card game after they likely will have spent a top starter to win that game.

This will give the top NL seed a better chance to both advance and play fewer games than the winner of the other NLDS series. Last year, the Cubs were the latter. They prevailed over the Nationals in an exhausting five-game series, while the Dodgers cruised to a three-game sweep over the Wild Card Diamondbacks.

2. Get Kris Bryant, Brandon Morrow, Addison Russell, and Jason Heyward back healthy

You can’t hurry love, and you can’t make injuries heal. So this is less an action item and more a hope-it-happens. However, once each players returns, Joe Maddon must determine how best to get them sharp while managing playing time to avoid any recurrence of injury.

For example, will Maddon give Bryant more outfield starts to reduce shoulder-jolting dives at the hot corner? Will he avoid back-to-back appearances by Morrow until the playoffs?

3. Rest Willson Contreras

I recently noted Contreras’s high 2018 workload, and his overuse has continued since then. The consequence of catching 85 percent (24 of 28) of the team’s games in August has been the worst offensive month of his starting career. The drop-off to backup option Victor Caratini was steep, but with the trade for the more defensively steady Bobby Wilson, one hopes rest for Contreras results in rejuvenation of his bat.

4. Set playoff rotation

The Cubs playoff rotation will uniquely feature three left-handed starters and Kyle Hendricks, but in what order? Jose Quintana is undoubtedly your No. 4. Since Jon Lester and Cole Hamels feature similar styles, should Hendricks break up those two? And should Hamels or Lester take Game 1?

Maddon does not need to decide immediately, but he has determined a preferred rotation order by mid-September in the past. This has allowed him to give his starters additional days off in ways to better line them up for the postseason starts.

5. Final Playoff Roster

Save unforeseen injuries, the 14 position players seem set. I presume Maddon goes with Caratini over Wilson for his bat against righties and positional flexibility, but if the younger backstop’s newfound offense (four for his last 11) slumps again, maybe Wilson gets closer consideration.

On the pitching side, going with four starters and seven relievers probably leaves just two bullpen slots there. Steve Cishek, Pedro Strop, Carl Edwards Jr. and Justin Wilson are guarantees. Morrow as well if healthy.

That leaves Brandon Kintzler and Jesse Chavez from the right side and Mike Montgomery, Randy Rosario and a very long-shot Drew Smyly from the left. A lot will come down to stretch-run performances, as well as whether an extra lefty is needed against a particular team’s lineup.

6. Playoff Scouting & Game Planning

Sending scouts throughout the NL to appraise possible playoff opponents is obligatory and what a team does with that information is critical. After all, defensive positioning, late-game substitutions, and optimal offensive and pitching match-ups do affect outcomes in October.

For example, the Cubs experienced one of the bigger game-planning boners against the Mets in the 2015 NLCS. Daniel Murphy finished the regular season with back-to-back months well above his career average OPS (.862 and .844). He followed this in the NLDS by dominating the Dodgers with three homers and a 1.143 OPS.

Despite this, the Cubs’ game plan called for pitching to Murphy again and again and again. Four games later, he headed to the World Series as the NLCS MVP after hitting another four homers and a 1.850 OPS against the Cubs.

After that, the Royals wisely decided to pitch around Murphy in key situations and otherwise tried to beat him with something other than low-inside fastballs. Combined with some timely hitting of their own, that led to the 2015 title heading to Kansas City.

7. Set Postseason Relief Strategy

Given the challenges the Cubs’ starting rotation has had going deep into games, Maddon must face up to his own past playoff bullpen fears. He’s hated depending on more than two relievers with any lead. In 2016, Montgomery and Aroldis Chapman handled 10 of 13 relief innings in the team’s four World Series wins. Last year, Maddon tried to ride Edwards as Wade Davis’s set-up man, but this proved near disastrous.

This year it will behoove Maddon to revamp his simplistic, undermanned bullpen approach. One hopes Morrow returns healthy, but either way, Maddon must commit to a deeper bullpen approach. Trusting Strop to protect his first playoff lead later than the 7th inning since 2015 will be a good start.

And given the starters’ shorter appearances this year, should Maddon plan to use Montgomery for multiple relief innings in Game 1? This could allow them to get deeper into games without exhausting top relievers with extended outings and could be a novel solution to the team’s pitching challenges this year.

8. Set Postseason Power-Arm strategy


The key statistical difference between the Cubs in 2016 and 2017 was their record in games started by an elite opposing pitcher. In 2016, the Cubs battled those pitchers to a 4-4 draw and dominated all other starters. In 2017, they again fared well against non-elite starters, but were doomed by going 2-7 against elites.

Maddon keeps hoping his free-swinging young hitters will suddenly develop better approaches against power arms, but this is not happening. He has to play Contreras behind the plate and either Javy Baez or Russell at shortstop. But like a pizza crust stuffed with cheese, he should otherwise try cramming as many quality contact bats in the lineup as possible against elite power arms.

This means Ben Zobrist, Heyward, Almora and Murphy. Anthony Rizzo is just a .217 hitter in his career against power arms, but his numbers this year have finally started to rise with the rest of his stats. When healthy, Bryant is normally a good bet against power arms, but if his shoulder isn’t 100 percent, he’ll struggle to catch up with the heat.

9. Set Defensive Substitution Approach

This is normally right in Maddon’s wheelhouse, but in playoff situations he sometimes develops the yips. See failing to substitute Almora for Zobrist in Game 2 against the Nationals last year. If he does that, Almora may well catch Jordan Zimmerman’s winning three-run homer in the 8th that just barely cleared the wall.

Plus, with Murphy at second and Baez expected to log some shortstop time, determining when best to substitute out defensively in the infield will rival Maddon’s outfield decisions. Keep in mind that the Murphy-Baez keystone combination was shaky enough to add an extra 22 pitches to Cole Hamels’ pitch count against the Mets. That won’t do in the playoffs.

10. Work Out Extension for David Bote

Okay, this one was a ploy just to get you to read to the end of the story. Of course, whenever any Cub player not in his walk year has a good stretch or season, someone out there (usually ESPN’s Jesse Rogers) seems to declare the Cubs must lock him into an exorbitantly expensive long-term deal. See Tyler Colvin, Jake Arrieta, Welington Castillo, and Dexter Fowler as just a few examples.

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