The 3 Biggest Questions for the Chicago Cubs Down the Stretch

The Chicago Cubs have made a lot of miracles happen this year.

Somehow, they've managed to still be a steadfast playoff contender even with the sheer bad injury luck that has hampered the team for nearly the entire season.

But the Cubs aren't entirely out of the woods. A walk-off loss to the Seattle Mariners late Friday night (or perhaps early Saturday morning) means they're back to a six-game gap to the first-place Milwaukee Brewers, and their lead atop the National League Wild Card standings has dwindled to three games as the Philadelphia Phillies surge.

The Cubs have a formidable squad capable of beating any team in MLB, but there are still a few big questions that remain as August nears its end.

Where Will Javier Assad Fit Within the Pitching Staff?

Aug 18, 2026; Chicago, Illinois, USA; Chicago Cubs pitcher Javier Assad (72) reacts against the Chicago White Sox during the fifth inning at Wrigley Field. Mandatory Credit: Patrick Gorski-Imagn Images | IMAGN IMAGES via Reuters Connect

Javier Assad's case has only grown more curious in the last week.

The right-hander has slowly become one of the Cubs' most reliable arms over the course of the season. He has a 3.46 ERA over 22 appearances (10 starts) in 83.1 innings, and has been even better over his last 15 games with a 2.43 ERA and a 1.04 WHIP in 59.1 innings.

Javier Assad is the unsung hero of the Cubs pitching staff 🔥

Last 10: 2.62 ERA
Last 20: 2.82 ERA
Last 30: 3.52 ERA
Last 40: 3.86 ERA
Last 50: 4.11 ERA
Last 60: 3.61 ERA
Last 70: 3.53 ERA
Last 80: 3.33 ERA
Last 90: 3.40 ERA
Last 100: 3.43 ERA pic.twitter.com/TplRw5hAO8
— The Windy City Breakdown (@wcb_pod) August 19, 2026

His consistency on the mound is evident. So why is he constantly moving between MLB and Triple-A?

Craig Counsell told reporters in Seattle that he knew Assad's recent performance "doesn't warrant" being in the minors.

"The way Javy's pitched definitely doesn't warrant going to the minor leagues ... In Javy's case, he's there in case someone gets hurt. That's what this is really about. Preserving depth."

The 29-year-old has already been optioned to Iowa four times this season. He began the campaign in Triple-A, and, while he struggled in April upon being recalled (7.58 ERA, 19 IP), he has a 2.24 ERA since May 1.

His subsequent options have been based on strategy and not performance. He went down on May 17 to be stretched out to start once injuries started piling up on the rotation. He returned on June 7, and in the 14 games he's appeared in since, the Cubs are 12-2.

Now, he's been optioned twice in the last week.

Assad's underlying numbers do cause some concern. His 16.6% strikeout rate is the 14th-lowest in MLB among the 143 pitchers who have pitched at least 80 innings this season. His FIP of 4.35 indicates that he's getting a huge lift from the Cubs' defense.

Those are things that would matter if he wasn't getting outs. But Assad has proven that he's exactly that type of pitcher: An innings-eater and out-getter who can provide a safety net at will.

Assad wasn't on the Wild Card Series roster against the Padres last season after he started Game 162 and wouldn't be available anyway. But he was left off the NLDS roster, which was a bit of a head-scratcher. Assad dealt with an oblique strain for the majority of 2025 and only pitched 37 innings beginning in August, but he was in fine form and seemed to be a good long-relief option for the Cubs in the playoffs.

If Assad truly has a place on the staff and is healthy through the end of the regular season, he should certainly make a potential postseason roster. That will be the most interesting thing to monitor as the season nears its end.

Will Matt Shaw Have a Role Carved Out?

Jun 20, 2026; Chicago, Illinois, USA; Chicago Cubs right fielder Matt Shaw (6) rounds the bases after hitting a three-run home run against the Toronto Blue Jays during the second inning at Wrigley Field. Mandatory Credit: Patrick Gorski-Imagn Images | IMAGN IMAGES via Reuters Connect

Matt Shaw had only recently returned from a three-week IL stint when he fouled a pitch off his left hand in the Cubs' 4-3 win over the Brewers on June 28. The pain persisted the following day, and Shaw went back on the IL with a hand sprain.

His recovery progress has ebbed and flowed since then, with Counsell on Aug. 8 telling reporters it was going "a lot more slowly than we would have hoped."

But Shaw looks to finally be nearing a return after he played for Triple-A Iowa in a rehab assignment on Aug. 19. He went 1-for-3 and played five innings at second base. In his second game Friday night, he went 2-for-4 with two RBI.

Matt Shaw drives in a pair! pic.twitter.com/CVzWGGThNp
— Iowa Cubs (@IowaCubs) August 22, 2026

Shaw was looking to perhaps be the Cubs' third baseman of the future last season, but that plan took a turn when the Cubs signed Alex Bregman to a five-year deal in the offseason.

In the 56 games he's played in 2026, Shaw has logged 187.2 innings in right field, 46 at second base, 34 at third, 11 in left, 10 at first and seven in center field. He's been a true 'super utility man' — but can the Cubs give him regular playing time, even with Dansby Swanson out injured?

Nico Hoerner will pick up the starts at shortstop with Swanson out, which has given Pedro Ramirez an everyday role at second. Ramirez has been impressive with his bat as well, slashing .277/.340/.404 (.744 OPS) with two home runs and 15 RBI in his first 87 MLB games.

Seiya Suzuki has excelled in right, and Michael Conforto can play there as well. The Cubs also acquired outfield help in Tyrone Taylor at the trade deadline and just recently claimed infielder Gabriel Arias off waivers.

Shaw does have the defensive advantage over Conforto in right field based on Outs Above Average, but Ramirez has been the better defender at second.

It will also come down to whether Shaw's bat is missed enough in the Cubs' lineup. He's slashing .246/.322/.415 (.737 OPS) with four home runs and 20 RBI this season, which is just about on par with what Ramirez is doing — even though Ramirez is just 9 for his last 47. Conforto, however, is hitting just .105 in his last 15 games and that could be enough to return Shaw to a backup right fielder role. Shaw did assume the starting right fielder role early in the season when Suzuki was dealing with a knee sprain.

The Cubs have not yet determined a return date for Shaw, but if it's nearing, then the Cubs will have some intriguing decisions to make.

Who Is Craig Counsell's Closer?

Knoxville Smokies pitcher Daniel Palencia (18) leaves the mound after being relieved during a Minor League Baseball game against the Rocket City Trash Pandas on Aug. 11, 2026, in Knoxville, Tennessee. | USA TODAY Network via Reuters Connect

The Cubs made a long-awaited roster move on Friday, activating resident flamethrower Daniel Palencia from the 60-day IL. The right-hander first went down on June 16 with right elbow inflammation after pitching to a 2.55 ERA in 16.2 innings of work. He notched three saves out of three opportunities across his 19 appearances.

The 26-year-old made a name for himself last year when he became the Cubs' closer who trotted out to a light show and Daddy Yankee's 'Gasolina' blaring out of the Wrigley Field sound system. He had a 2.91 ERA in 52.2 innings and converted 22 of 25 save opportunities.

Palencia returned to action Friday, entering the game in the seventh inning and tossing a scoreless frame with two strikeouts to boot. He did what Counsell said he was there to do.

"I think one of the biggest things is he just needs to get innings under his belt," Counsell told reporters Friday.

With Palencia's limited innings this season, it's not guaranteed that he can jump right back into the closer role.

Even so, Jacob Webb has emerged with authority and is riding a 24.2-inning scoreless streak. He's a different type of pitcher compared to Palencia — lower velocity and won't strike out as many batters — but Webb can absolutely get the job done too. He's 7-for-7 on save opportunities since July 1 and has nine total on the year.

Jacob Webb since June 21st:

24.2 IP | 0.00 ERA | 0.93 WHIP | 25 K | 10 BB

His scoreless innings streak is the longest active streak in baseball! pic.twitter.com/OZ2TwMk39a
— Just Baseball (@JustBB_Media) August 22, 2026

The Cubs have also given late-inning opportunities to deadline acquisition Ryan Zeferjahn, though they haven't quite panned out as hoped. Zeferjahn has a 7.50 ERA in just six innings with Chicago, and he blew his first save opportunity against the White Sox on Aug. 17.

If Palencia can be ramped up by the playoffs, he'll be the high-octane closer the Cubs will want and need in October.

Sign up for our free newsletter to stay up-to-date with all things Chicago Cubs.

Add us as a preferred source on Google