Mid-season thoughts on the Cubs offseason

Coming off a relatively successful season in 2025 that included a Wild Card series win, and then a disappointing 3-2 series loss to the Brewers, the Cubs had work to do if they were going to return to the postseason.

A couple things have changed the equation for 2026:

1. Injuries has decimated the pitching
2. The Brewers are again playing well above expectations, making a division title unlikely

But beyond those two factors, let’s take a look at the offseason moves, and how they look half way through the 2026 season.

Here are some of the players they lost, and the holes they had to fill

First, here are some players they had before the trade deadline who they had to replace:

• Kyle Tucker – the biggest loss on offense, I think most of us thought the Cubs needed to replace 1st half Kyle Tucker from 2025, who was in the MVP conversation. The Dodgers have gotten 2nd-half Kyle Tucker, who has a 106 wRC+, .731 OPS, -2 DRS (defensive runs saved) and is costing the Dodgers $57 million against the luxury tax this season. If he had these numbers for the Cubs, he would be getting raked against the coals. But on the Dodgers, his poor season can be hidden within a team of superstars, and the Dodgers can still have the best record in baseball.
• Brad Keller – from non-roster invitee, to best reliever on the team, Keller was a revelation for the Cubs in 2025. He cashed in on the great year with a 2-year, $22 million deal with the Phillies to be a setup man. Year one had been just OK, as he has a 4.15 ERA and a 1.35 WHIP (compared to 2.07 and 0.96 in 2025) – numbers that do not justify how much he’s being paid. He is just finishing up a stint on the IL with forearm tendinitis.
• Owen Caissie – He would have been in competition for the DH/RF spot that has been been filled by Ballesteros, Shaw and Conforto. He had a rough start, but the Marlins stuck with him, and he’s shown power. But a 101 wRC+, .755 OPS and 0.2 fWAR are not exactly setting the world on fire. His defense has been especially bad, with a -6 DRS.
• Justin Turner – Turner was supposed to be replaced by Tyler Austin, to give them a right-handed hitter who could DH against lefties, and give Michael Busch an occasional day off. Austin has been hurt, so it has been Shaw (when healthy), Pedro Ramirez and Alcantara doing most of the DH work from the right-side.
• Reese McGuire – So far, knock on wood, the Cubs have not needed a third catcher, although Ballesteros would probably be the guy if needed. McGuire signed with the Brewers, but was replaced as the backup by Gary Sanchez before the season even started. He moved on to the While Sox, where he struggled badly at the plate, with a .445 OPS (his slugging alone in 2025 was .444) and a 35 wRC+ in 34 plate appearances. With Kyle Teel returning from injury, the White Sox just released him.

The there were the mid and late-season acquisitions

• Drew Pomeranz – a mid-season waiver pickup, Pomeranz was excellent for the Cubs. He was not so good for the Angels, where he signed a 1-year, $4 million deal. The Cubs are only the hook for about $391k in 2026, which could be a steal. His ERA with L.A. was not terrible, at 5.01, but his WHIP was 1.59. We’ll see if he contributes anything to the Cubs – but for now, he is a healthy arm with major league experience.
• Willi Castro – he was terrible for the Cubs after the trade last season (a 40 wRC+ and .485 OPS), bt has had a mile bounce back with the Rockies at a .719 OPS and 88 wRC+. His 2-year, $12.8M deal doesn’t look too bad, so I could see a contending team try to pick him up at the deadline this season.
• Michael Soroka – he has turned out to be the biggest surprise among players the Cubs did not bring back. He was damaged goods when the Cubs traded for him last season, pitching in only 6 games (1 start). But this season, he has a 3.07 ERA in 15 starts for the Diamondbacks – a relative steal for his $7.5M salary. He did have a glute injury and had missed his last several starts – so maybe he’s still a Cub in spirit.
• Andrew Kittredge – the Cubs sent him back to the Orioles rather then pick up his $9M club option. The Orioles did pick it up, and he has a 4.91 ERA, although most of that damage was done in one game on May 3rd, where he gave up 7 earned runs in one-third of an inning. He’s been much better lately, only giving up 1 run over his past 10 games. Could the Cubs try to get him again this season? Maybe.
• Taylor Rogers – While his brother Tyler is having a nice season for Toronto, Taylor has not been as good. He has a 5.73 ERA over 33 innings for the Twins. He’s still good against lefties, as they are hitting .254 and slugging .313. But righties are killing him, with a .344 average and .578 slugging percentage. He was made for the days when you could bring him in to face one or two tough left-handed hitters, but in the days of the 3-batter minimum, he is not very effective.
• Aaron Civale – a late season waiver pickup, Civale signed with the A’s for $6M, and has given them innings, logging 72.1 IP in 15 starts, with a 5.10 ERA. Certainly not a top-line guy, but at that price, anything more would be as surprise.
• Carlos Santana – seems like the end of the road for this former All-Star. and gold-glover. Santana was terrible with the Cubs a right-handed hitting pinch hitter with a .263 OPS in 19 plate appearances – which seems almost impossible statistically. But he followed it up with a .279 OPS in 26 plate appearances with the DBacks this season before he was released. He has not given up, signing a minor league deal with the Braves.

That’s a fair number of players to replace, although many of them were at the fringes of the team last season. Here were the replacements:

Alex Bregman – As bad as Tucker has been for the Dodgers, the guy who – despite playing a different position – was his replacement. He has been much worse than expected, especially at the plate. Here a comparison of the two

Player	OPS	wRC+	DRS	fWAR
Bregman	.689	96	+10	2.3
Tucker	.731	106	-2	1.2

Tucker has been slightly better at the plate, but Bregman has provided much more value on defense. Disappointment on both sides here, but I don’t how the Cubs would be any better with Tucker as opposed to Bregman for this season.

Edward Cabrera – He’s had a rough season any way you slice it, with injuries piled on top of mediocre or poor performances. He’s has a few decent games sprinkled in, but they’ve been few and far between. There was lots of talk that the Cubs might go for a free agent, like Michal King and Tatsuma Imai. Here’s a comparison between him and Soroka

Player	Yr/AAV	IP	ERA	WHIP
Cabrera	3 / $4.45m	72.1	5.10	1.40
Soroka	1 / $7M	82.0	3.07	1.09
Imai	2 / $18M	52.0	6.06	1.50
King	3 / $25M	102.1	3.52	1.16

Obviously, Cabrera is the cheapest of the bunch, although he did cost Owen Caissie in a trade. Imai and King both have opt-outs after this season. Bringing back Soroka on an affordable contract seems like it would have been the right move, as the Cubs were not swimming in the waters of the big free agent contracts to King or Dylan Cease. But there are many other affordable starters who have not been great. So far, this deal has been a dud, but there is plenty of time for it to get better.

Hunter Harvey – he had injury concerns when he was signed to a 1-year, $5M deal, and they were warranted. The Cubs tried to be careful, never pitching him on back-to-back days, but it was to no avail, as he only logged 4 innings before a triceps injury. News on his recovery has been scarce, and a return date is unknown. Perhaps he can give them some innings in the stretch run, but who even knows.

Phil Maton – He has a slightly larger AAV than Harvey at $7.25M, but also has 2 guaranteed years on his deal. His great track record seems like a distant memory, as he’s compiled a 6.08 ERA in 26.2 innings. He is on his second IL stint with a bad knee, and Cubs’ fans can only hope that the injury has been the root cause of his poor performance. Otherwise, he might win the Hector Neris/Ryan Pressly award for failed former Astros pitcher in a Cubs uniform (although, he hasn’t been with Houston since 2023). It should actually be named for Dave Smith, who was a big free agent signing back in 1991, and produced a 6.00 ERA in 33 innings.

Hoby Milner – Milner was used and overused in his first couple of months as a Cub, pitching in 38 of their first 81 games . But it was not a pitching injury that took him out of commission for 4 to 6 weeks, but an emergency appendectomy. Brought in as a lefty-specialist, he’s actually been good against both lefties and righties this season (.258 avg/.359 slg vs LH, .254 avg/.418 slg vs RH).

Jacob Webb – I was not sure he’d make the roster out of camp, and we ready to see him DFA’s after the first couple of weeks of the season, but fortunately, I am not running the Cubs’ front office. He had a dominant month of May, and despite some recent regression, has still been very effective, especially considering his $1.5M salary with a club option for 2027. He has a 3.26 ERA in 38.2 innings, and is absolutely in Craig Counsell’s circle of trust.

Here is a comparison of the Cubs 4 primary free agent pickups, versus the main guys that they lost

Player	Yr/AAV	IP	ERA	WHIP
Keller	2 yr / $11M	30.1	4.15	1.35
Kittredge	1 yr / $9M	22.0	4.91	1.36
Rogers	1 yr / $2M	33.0	5.73	1.61
Pomeranz	1 yr / $4M	23.1	4.97	1.59
*Total	$26M	108.2	4.99	1.54

Player	Yr/AAV	IP	ERA	WHIP
Harvey	1 yr / $5M	4	6.75	1.59
Maton	2 yr / $7.25M	26.2	6.08	1.76
Milner	1 yr / $3.75M	35.2	3.53	1.21
Webb	1 yr / $1.5M	38.2	3.26	1.34
*Total	$17.5M	103.6	4.26	1.51

*Total Salary is for 1 year of AAV

So, looking at these numbers, the players that the Cubs signed to replace their primary losses in the bullpen have done slightly better than the players they replaced. Although, you certainly can’t call it a success. And with the injury to Daniel Palencia and move of both Colin Rea and a pre-injury Ben Brown to the rotation, the Cubs have had to scramble to find healthy, let alone effective, arms for the bullpen. Fortunately, Ryan Rolison and Trent Thornton have been pretty good, and they’ve gotten some key contributions from others.

Michael Conforto – he was a mid-Spring signing coming off a poor season with the Dodgers. After a rough start, he has been a very effective hitter, with a .827 OPS and 126 wRC+ in 152 plate appearances. And the fact that the Cubs only owe him $2 million this season makes it even better. While Moises Ballesteros has struggled, the signing of Conforto has eased that disappointment, and he has become the primary DH/RF against left-handed pitching.

Tyler Austin – on the other side of that spectrum is Tyler Austin, who was signed out of Japan for $1.25M to provide a right handed hitting depth at first, DH and corner outfield. He never even made it to a Spring Training game, as a workout injury to his injury required major surgery. He was a cheap, speculative signing, so it really did not have much impact.

If the Cubs had kept Caissie and used him as the DH versus right-handed pitching, he is the comparison with the numbers we’ve seen from Conforto and Ballestros.

Player(s)	PA	HR	RBI	wRC+	OPS
Caissie	246	12	50	101	.755
Ballesteros & Conforto	351	13	45	101	.725

The obvious edge goes to Caissie, with a higher OPS, 1 more home run and 5 more RBIs in over 100 fewer plate appearances. Although, the wRC+ is identical.

My biggest takeaway from this analysis is that the Cubs would not be better off if they had kept their 2025 roster together, but they also did not improve themselves with the roster moves they chose to make. While they still are holding on to the top Wild Card spot in the NL, I think they need Bregman and Cabrera to have much better 2nd halves of the season to stay in the playoff picture.