Cubs ‘Still Looking for Upgrades’ as Another Late Loss Exposes Flaws

Even when they were clinging to first place in spite of themselves, it was clear the Cubs had flaws to address. And that was before the bullpen blew a tenuous late lead, in part because the offense had scratched out just two runs against a middling starter. But help is on the way. Hey, why’s everyone so quiet? I said help is on the way!

Prior to loss in Milwaukee, the Cubs bit the bullet and made a deal to pry a lefty reliever away from a Giants team that looks to be buying otherwise. Okay, so it was actually a low-key move that included cash going both ways for a guy who’d been designated for assignment after putting up a 5.90 ERA with 35 walks and 17 home runs allowed in just under 69 innings.

Wait, why did the Cubs go Dutch on Derek Holland? The simple answer is that they’re hoping changes of scenery and usage will allow him to excel for them. Holland was brutal as a starter and wasn’t exactly good after being shifted to the bullpen in early May, but he does have a particular skill that the Cubs think they can leverage.

Holland has held left-handed batters to a .182 average (14-for-77) and .471 OPS this season, significantly better than his career marks of .234 and .620 over parts of 11 seasons. That’s largely a function of a streamlined pitch mix that sees him going exclusively with the fastball, sinker, and slider against lefties. He’s eliminated his curve and change entirely and it seems to be paying off.

“He’s throwing the ball really, really well against lefties,” Theo Epstein said Friday. “It’s been a long track record of success against lefties, especially this year. He’s really been dominant against them. The Giants, they have three really good left-handers in the ‘pen already, so we can alter his role a little bit.

“Obviously, he started the year starting for them and then went into more of a long role. But, I feel like we have a chance to maybe, initially at least, target his role where he’s matching up against lefties. Put him in a position to succeed. I think there’s a real chance he can help us.”

Ed note: That quote and others included here came via’s Jordan Bastian, who has a PhD in interview transcription science. His blog post is linked above, but I want to point that out specifically because Ol’ Dirty Bastian’s skills are mind-blowing.

One potential issue here is that Holland was not happy with being moved from the rotation and was openly critical of the Giants front office in when that decision was made in May. You have to wonder, then, whether he’s really amenable to taking on more of a LOOGY role. Then again, a good deal of his frustration stemmed from what he felt was an unnecessary IL placement for a “fake” finger injury, and you know that won’t be a problem for him with the Cubs.

“I talked to him today,” Epstein said. “He couldn’t be happier to be joining the Cubs. He expressed a willingness and an eagerness to embrace any role and to contribute any way he can.”

Assuming Holland toes the line and continues to perform somewhere between his season and career numbers against lefties, this move should work out well. But the Cubs can’t project Holland as a lights-out lefty specialist, nor can they assume Joe Maddon will deploy him properly, which means they still need to be looking for more help on the relief market.

“We’re still looking for upgrades, yeah,” Epstein admitted. “If the right opportunity presents itself or we can get another weapon from the left side, we’d love to jump on that. I think the kind of independent of the move today, the market for left-handed relievers might not fully materialize the way the industry expected it to.”

Epstein is alluding to the same thing I mentioned in the lede, which is that the Giants are apparently now inclined to hold onto southpaws Will Smith and Tony Watson. Both had been mentioned as Cubs targets, though other teams were equally enamored of them. Taking two capable lefties like that off the table shifts supply significantly and could increase the asking price for guys like Jake Diekman and Andrew Chafin.

Those latter two are among several other names tied to the Cubs, though neither feels like the type of pitcher who’d really put the Cubs over the top. And because they’re either even- or reverse-split guys, you have to wonder how keen Epstein would be on bringing them aboard. Which is to say he may want to better Maddon-proof the bullpen for the stretch run.

The Cubs skipper has never scored high marks for his bullpen management and seems to favor lefty-lefty or righty-righty matchups even when the numbers scream otherwise. Several left-handed batters owe Maddon a few batting average points for getting to face Mike Montgomery this season, and we could surely find other situations if we liked.

Having a guy like Holland might mean seeking out another pitcher whose performance isn’t reliant upon facing like-handed batters. And that isn’t just a knock on Maddon, it’s the simple fact that getting more specialized with one move could mean reinforcing flexibility with another. The same thing applies to their position-player roster, which will probably look different come August 1.

“We’re definitely still looking for improvements, both sides of the ball,” Epstein said. “Yeah, the right professional at-bat, the right position player, I think could certainly still improve our depth and help us.”

Their moves on that front may be tempered by Ian Happ‘s promotion and the news that Ben Zobrist is planning to begin a rehab assignment next week. Not to mention Robel Garcia‘s emergence, which gives Cubs a versatile slugger who can run into pitches and provide a spark off the bench. If they believe Zobrist can be anything close to the player he was in 2016 and ’18, there may be no need to target a second baseman.

So maybe they still go for Nicholas Castellanos, but as more of a luxury than a necessity. Perhaps they’re able to pry Hunter Pence from the Rangers or Billy Hamilton from the Royals to serve as that one-dimensional speedster to help with defense and baserunning. Those are the moves you can make when you’ve got a versatile bench that isn’t very dynamic.

It’s hard to see the Cubs doing anything really splashy over the next few days, even after another highly disappointing performance Friday night, but you can never really rule anything out with this front office. Such a loss may be enough to spur them to go big, but is could also have offered proof that the issues are too big to paint over with a couple trades.

And hey, there’s still time for improvement to come from within as performance wins out over talent. Right? Is anyone still there?

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