4 Questions Cubs Must Answer as Trade Deadline Approaches

With the July 31 non-waiver trade deadline firmly in sight, the national media focuses largely on big names like Manny Machado and Cole Hamels. But given the Chicago Cubs finite trade assets, they must be far more targeted to improve chances to win the division and go deep into the playoffs.

For instance, the Cubs’ young lineup performs well below league average against power arms but excels against all other types of pitchers. So adding someone like Toronto’s Josh Donaldson who features the same splits would expend limited resources while doing little to improve the team’s chances.

So what players should they target? To help, here are four key questions, as well as my best guess on which direction the front office will go.

1. Let it ride on rotation?

First a reminder of one key to the Cubs’ 2016 success and their 2017 stumble:

Throw in 2015, when Cubs went 0-3 against the Mets’ elite trio of Matt Harvey, Jacob deGrom, and Noah Syndergaard, and the point is clear. When the Cubs play other teams’ elite starters to a draw, they have a title shot. When dominated, they head home early.

The clearest way to neutralize elite pitchers is to counter with elite arms. Flash back to Game 1 of the 2016 NLDS when Jon Lester out-dueled the Giants’ Johnny Cueto for a 1-0 victory. For the rest of October, the Cubs followed Lester with Jake Arrieta and Kyle Hendricks.

With this year’s signing of Yu Darvish, the Cubs again hoped to stack their rotation. Unfortunately, only Lester is pitching like an elite starter so far. That leaves as options either trading for another ace or getting a big rebound from at least one of Hendricks, Darvish or Jose Quintana.

My guess: The front office lets it ride. Over the past 12 months, the Cubs invested heavily in the rotation via both free agency (Darvish, Tyler Chatwood) and trade (Quintana). Trading for another top starter would leave few trade chips for other need areas. So as much out of necessity as anything else, they need to bank on their current starters.

2. Who sets up Morrow?

Assuming Brandon Morrow has his annual injury scare out the way, bullpen questions revolve around the rest of the back end. This team inherited no setup relievers who Joe Maddon trusts with a postseason lead. Steve Cishek was a very promising back-end signing, but if Maddon wants a dependable Cishek come October, he must conserve the sidewinger as carefully as Morrow moving forward.

Even then, at least one more quality back-end arm is needed to bridge playoff leads to Morrow. Carl Edwards Jr. and Drew Smyly are both rehabbing, but neither are ideal bets. Edwards has yet to prove consistent in high-leverage situations, and Smyly’s rehab from Tommy John surgery leaves questions that won’t be answered until well past the July 31 trade deadline.

My guess: As in the past two years, they bolster. The only question is how big do they go, which brings us to…

3. Rental vs. long-term?

The obvious trade-off is that a rental costs less in trade-asset treasure. But if you give more, you can possibly fill a long-term need. A classic example is the Cubs’ 2016 choice between Aroldis Chapman (rental) and Andrew Miller (two-plus years of control). Both were dominant relievers. Both delivered strong postseasons.

The Cubs ultimately went rental that season, but they’ve also invested with mixed results in longer-term acquisitions such as Quintana, Mike Montgomery, and Justin Wilson. With fewer trade chips available this year, the question of rental versus long-term represents a critical decision.

The Orioles’ Manny Machado is the best known rental out there. Short-term relief include Jeurys Familia (Mets), Adam Ottavino (Rockies), and Zach Britton (Orioles). Yet the real white whale for the Cubs is probably Padres lefty Brad Hand, an All-Star closer who is under control for another three seasons. His price will be accordingly steep.

My guess: The bullpen definitely gets bolstered. To harpoon the white whale, they will need to empty most barrels. It’s tempting, but other teams will have far more with which to outbid them. Ultimately, I see the Cubs trading less to get a young, controllable setup man. If a reasonable trade match can’t be found there, then a rental reliever for a couple middling prospects is the backup plan.

4. Lineup help against power arms?

This is by far the most interesting – and potentially most creative – area to weigh. Here are the 2018 numbers for current Cubs hitters:

Quite tellingly, none of the Cubs’ top five hitters by total plate appearances (Rizzo, Bryant, Baez, Schwarber and Contreras) have hit power arms well this year. And with the exception of Bryant, none have in their careers. Herein lies the crux of the the team’s struggles against playoff power starters.

This recommends Maddon stacking his lineup against power arms as much as possible, just as he would against a starter with extreme lefty/righty splits. But Maddon has generally avoided this. Despite all the different lineup combinations he’s employed in his three-plus years with the Cubs, he’s never started Heyward, Almora, Zobrist, and La Stella at the same time.

The most logical explanation probably concerns La Stella’s defense. This is understandable, as any loss of defensive run prevention can negate the offensive gains. This is also the biggest argument against acquiring Machado to play shortstop.

But Maddon’s aversion just bolsters the argument to add another proven bat against power arms. The Cubs could then start four strong bats and pinch-hit La Stella as run-scoring opportunities arise. Once you chase that power starter, substitute back in with your young bats to go at those middle relievers.

Finding a good bat against power arms, though, is easier said than done. Here are possibly available players who feature strong numbers against power arms this year and in their careers. I’ve also excluded options at first base and catcher, as it’s unlikely Maddon will sit Rizzo or Contreras in a playoff game.

Machado and Parra are both rentals, though the latter has a team option for 2019 ($12.5M with a $1.5M buyout). Gennett is a controllable All-Star-caliber hitter and would probably cost the most, if available. Pillar and Anderson are both everyday players, but since the Cubs wouldn’t use them that way, they are unlikely to pay a premium price there. Dietrich has positional flexibility, but isn’t great defensively.

To my eye, Duffy and Parra offer the most intrigue. Their trade price should be modest, leaving chips for a bullpen addition. Duffy has just an average glove, but some positional flexibility. Parra is a plus defender at the corner outfield positions and brings a veteran presence. He also does not complicate the Cubs’ free agency math if they choose to target either Machado or Bryce Harper this winter.

My guess: Yours is as good as mine here. Short of adding an ace starter (unlikely), another skilled power-arm bat is the best way to improve playoff-win probability. But it’s unclear whether the team recognizes this. Their two best power-arm bats (Zobrist, Heyward) have actually logged 10-15 percent fewer plate appearances against power arms than Schwarber and Baez, and just as many as Happ with his 60 percent power-arm K-rate.

If the Cubs don’t upgrade in this area, everything rides on the starting pitching rebounding to duel opposing elite starters to a draw and having enough back-end bullpen strength to hold playoff leads. Why gamble with a title shot if a cheap insurance chip is available?