Sam Caulder

Image courtesy of © Saul Young/News Sentinel / USA TODAY NETWORK via Imagn Images The 2026 MLB regular season is quickly coming to an end, and it’s been quite the eventful year for the Chicago Cubs. The major-league roster is currently in a fight to hold onto its Wild Card spot, with the Cubs hoping all of the work they’ve put in throughout the season will be enough to get them back to the postseason. But while there’s obviously plenty of attention on what’s happening at the major-league level, there’s also been a ton of movement throughout the farm system. Some prospects had breakout seasons and saw their stock skyrocket as a result. Others struggled, dealt with injuries, or simply didn’t take the steps forward that many expected, causing them to slide down the prospect rankings. And then there are guys like Moisés Ballesteros, who began the year as North Side Baseball’s top prospect before being traded at the deadline. With all of that movement, it feels like a good time to take a look at some of the biggest risers and fallers in the Cubs’ prospect rankings this season. Cubs' Biggest Prospect Risers (2026) The biggest riser has to be catcher Owen Ayers. The backstop started the season outside of North Side Baseball’s top 20 prospects. Now, he sits at No. 4. That’s a pretty significant jump, but it’s also one that Ayers has earned. After starting the year at High-A South Bend, he will finish the season in Triple-A Iowa barring a September call-up. That means he’s gone from outside the top 20 to knocking on the door of the major leagues in a matter of months. And the dude has done nothing but rake. Across 118 games between his three different stops this season, Ayers is hitting .295 with a .409 on-base percentage and a .952 OPS. Those numbers are impressive enough on their own, but his overall profile makes his breakout season even more intriguing. Ayers has shown some impressive athleticism for a catcher, stealing 13 bases while also continuing to develop into a legitimate power threat. His power production has grown exponentially throughout the year, giving the Cubs another reason to believe he could eventually be more than just a defense-first catcher. There’s still plenty that needs to happen before Ayers can establish himself as a long-term major league catcher, but it’s hard not to get excited about where he is right now. If everything continues trending in the right direction, we could hopefully see him in Chicago early next season. Another massive riser is Josiah Hartshorn. Hartshorn opened the year as North Side Baseball’s No. 9 prospect. Now, he’ll finish the year at the very top. That kind of jump doesn’t happen without a really impressive season, and Hartshorn has certainly provided one. In his first year in the Cubs’ system, the 19-year-old is hitting .289 with a .411 on-base percentage and a .940 OPS across 122 games between Low-A and High-A. There’s a lot to like about his offensive profile. He can hit for power, as evidenced by his 54 extra-base hits. He’s also shown a patient approach at the plate and enough athleticism to steal bases when he reaches. Put all of that together, and it’s easy to understand why his stock has risen so dramatically. There’s obviously still a long way to go, especially considering he has yet to play above High-A. But Hartshorn has put himself in a position where the Cubs have to start thinking seriously about his long-term future. He’ll only be 20 years old next season, so expecting him to reach the majors anytime soon would be aggressive... though he's certainly on the 2027 radar after exploding so thoroughly here in 2026. Cubs' Biggest Prospect Fallers (2026) As for a couple of prospects who saw their stock decline, let’s start with pitcher Brandon Birdsell. The 26-year-old began the season as the Cubs’ No. 11 prospect and currently comes in at No. 20. A lot of that has to do with the fact that he hasn’t played at all in 2026. He underwent elbow reconstruction surgery last summer, and he’ll now enter next season at 27 years old. That’s obviously not an ideal combination for a prospect who is trying to establish himself as a legitimate option for the Cubs’ future. Still, I think it’s too early to write him off. Birdsell looked solid in 2025 when healthy, and the biggest question right now is simply whether he can get back on the mound and stay there. That makes 2027 a very important year for him. Then there’s Jaxon Wiggins. Wiggins isn’t necessarily a faller because he dropped dramatically in the prospect rankings. He went from No. 2 at the beginning of the year to No. 3 currently. But if Wiggins were a stock, his value has crashed. Coming into the season, he looked like someone who could potentially develop into a frontline starter. Instead, he’s now being used as a reliever at Triple-A Iowa, and he has not looked good in that role. Wiggins owns an 8.24 ERA and a 2.02 WHIP across 31 2/3 innings at Triple-A. Perhaps most concerning, he has walked 31 batters during that stretch. The swing-and-miss stuff is still there, which is at least something to hold onto. Unfortunately, the control simply hasn’t been. Like Birdsell, though, it’s still too early to completely write him off. There’s a reason the Cubs viewed him as one of their best prospects coming into the season, and one bad year doesn’t erase all of the talent that got him there. But for someone a lot of Cubs fans, myself included, expected to be making an impact in the majors by now, this has been an extremely disappointing season for Wiggins. View full article

Owen Ayers and Josiah Hartshorn emerged as two of the Cubs’ biggest prospect winners in 2026. Meanwhile, Brandon Birdsell and Jaxon Wiggins saw their stock take a hit in very different ways. View full video

Image courtesy of © Patrick Gorski-Imagn Images The Chicago Cubs have spent much of this season searching for answers to their pitching problems. Injuries have forced Chicago to reshuffle its staff seemingly all year, and Ben Brown has been one of the more interesting examples of how much that situation has changed. Brown began the season in the bullpen, moved into the rotation when the Cubs desperately needed innings, and was pitching well in both roles before a neck injury shut him down in late June. He appeared to be making progress toward a return before Chicago recently made the decision to shut him down for the remainder of the season. According to manager Craig Counsell, the decision was ultimately about giving Brown more time to heal. “After consulting with doctors, it’s just more rest,” Counsell said. “There’s healing, but just not enough to allow the discomfort to go away. So, we just need to spend more time healing.” It’s undoubtedly a disappointing development for Brown, especially considering he had been sidelined since June with what was described as a stress reaction in his neck and had been on track to return before the end of the season. But while his 2026 campaign is officially over, the bigger question now becomes what his future looks like in Chicago. The good news is that Brown absolutely still has one. The Cubs may have spent much of this season dealing with injuries, but their pitching situation could look significantly different next year. Shota Imanaga and Kevin Gausman are both scheduled to reach free agency this offseason, potentially creating openings in the rotation. That could theoretically give Brown another opportunity to compete for a starting job when he returns. After all, he already proved this season that he can handle the role. Brown opened the year as a multi-inning reliever, working in two-to-three-inning bursts roughly twice a week. His first 12 appearances all came out of the bullpen, and he was extremely effective, allowing just six earned runs across 25 2/3 innings. Eventually, though, injuries to Matthew Boyd, Cade Horton and Edward Cabrera forced the Cubs to get creative. Chicago needed starting pitching, and Brown had already shown that he could provide length. The Cubs moved him into the rotation, and he responded by allowing just eight earned runs over eight starts. That stretch was important because it demonstrated that Brown isn't simply a reliever who occasionally provides multiple innings. He can start, he can handle a workload, and when healthy, he has shown flashes of being effective in either role. The problem is that staying healthy has become the biggest question. This isn't the first time Brown has dealt with an injury in his neck; a similar issue caused him to miss the final 96 games of the 2024 season. At some point, the Cubs have to start considering whether repeatedly asking Brown to prepare for and maintain a starter's workload is worth the risk. That doesn't mean he can't return as a starter. Depending on what happens with Imanaga and Gausman this offseason, Chicago may not have the luxury of immediately placing Brown in the bullpen. The Cubs could have an opening, and his experience starting this season should at least put him in the conversation. But long-term, relief may simply be the better decision. Brown's stuff has always looked like it could play extremely well out of the bullpen. His four-seam fastball sits around 96 mph and features plenty of life, and there's reason to believe that velocity could tick even higher if he isn't being asked to conserve energy for five or six innings every five days. A fastball that regularly reaches 97 or 98 mph is a completely different weapon coming out of the bullpen. His curveball is also capable of becoming a legitimate put-away pitch. Brown has leaned on his upper-80s knuckle curve throughout his career, and being able to attack hitters for an inning or two at a time could allow him to use both pitches more aggressively. And notably, the numbers suggest that his stuff simply played better in relief. Brown's hard-hit rate was just 34.2% as a reliever this season, roughly 14 percentage points lower than his mark as a starter. His average exit velocity was also two miles per hour lower, while he generated ground balls at a significantly higher rate. It's difficult to look at that kind of difference and completely dismiss it as a coincidence. Brown may have proven that he can make it as a big-league starter, but his profile appears to fit particularly well in a multi-inning relief role. The Cubs wouldn't necessarily need him to become a traditional one-inning reliever, either. His ability to provide two or three innings at a time would still give Counsell valuable flexibility. That may ultimately be where Brown's future becomes most interesting. Chicago has seen firsthand how quickly pitching depth can disappear, and having a pitcher who can work multiple innings out of the bullpen while also being capable of stepping into the rotation in an emergency is an extremely valuable luxury. Brown doesn't have to be locked into one role forever. He could become the type of pitcher who gives the Cubs options depending on what their staff needs at any given time. Still, after another extended absence because of the same area of his body, prioritizing his health should come before trying to turn him into a full-time starter. For now, though, none of that matters as much as getting him through this latest setback. The Cubs have made the right decision by shutting him down and allowing his neck more time to heal rather than rushing him back for a few appearances at the end of the season. Brown's future in Chicago hopefully won't be defined by this injury. He has shown too much ability for that. The question is how the Cubs can best maximize that talent moving forward. And while another opportunity in the rotation may be waiting for him next season, his long-term future may be much brighter coming out of the bullpen. View full article

Image courtesy of © David Banks-Imagn Images Every year, there are certain players that just seem to come alive in the postseason. Last year, we saw guys like Trey Yesavage and Ernie Clement play meaningful roles for the Toronto Blue Jays despite not necessarily lighting up the regular season (the former had spent nearly the entire year in Triple-A). Yet both became important pieces during Toronto’s postseason run, helping the team come within one win of a World Series title. Odds are good there will be multiple players who fit that description in 2026. And I think Matt Shaw has the potential to be one of them for the Chicago Cubs. When he’s been on the field, it’s been a promising year for Shaw. He’s made some notable offensive improvements, raising his OPS from .690 last season to .751 this year while also walking more, striking out less, and showing slightly more power. The Cubs are very likely going to be a Wild Card team this year. That means they're likely going to have to navigate the Wild Card round, and based on the current standings, they could find themselves facing one of the Phillies, Diamondbacks or Braves. Interestingly enough, all three of those potential matchups could line up quite well for Shaw. He hasn’t been an everyday player for the Cubs this season; instead, he’s settled into more of a short-side platoon role against left-handed pitching while also serving as a pinch-hitter late in games. It hasn’t been the most prominent role on Chicago’s roster, but the postseason could give him a chance to make a much bigger impact. The starting rotations the Cubs could see in October feature a lot of talented left-handed pitchers. Take the Phillies, for example. In a potential three-game Wild Card series, Cristopher Sánchez and Jesús Luzardo would both be lined up to start. Both left-handers have plenty of swing-and-miss ability, and with Shaw’s improving bat-to-ball skills, he feels like someone who could find himself in the lineup against either (or both) of them. He doesn’t necessarily need to turn into a completely different hitter overnight. If he can continue making contact, limiting strikeouts and taking advantage of favorable matchups, he could become a valuable piece against some of the best left-handed pitching in the National League. The same goes for the Braves and Diamondbacks. Atlanta’s rotation is headlined by Chris Sale, while Arizona has Eduardo Rodríguez. Both are left-handed starters, and both would present situations where I’d expect Shaw to be in the lineup. Then, there’s the possibility of advancing beyond the Wild Card round. If the Cubs make it to the NLDS or NLCS, they could potentially run into teams like the Dodgers or Brewers. And even in those matchups, there are left-handed pitchers who could give Shaw an opportunity. Guys like Tarik Skubal, Blake Snell, and Kyle Harrison are all examples of left-handed arms this team could potentially see during a postseason run. If one of those guys is on the mound, I’d have Shaw in the lineup. Of course, he doesn’t necessarily have to start to make an impact. One of the most valuable things about the postseason is that a player can completely change the course of a game with one at-bat. A clutch pinch-hit late in a close game could be the difference between moving on and going home, and the Cubs don’t have to look very far for an example of that. Just ask Miguel Montero. Montero famously delivered a pinch-hit grand slam against the Dodgers in Game 1 of the 2016 NLCS, helping the Cubs take a series lead before eventually winning their first World Series in more than a century. That’s the type of moment that can turn a player into a postseason hero. And while it would be unfair to expect Shaw to have a moment of that magnitude, his skill set and defensive versatility could give him an opportunity to make a contribution off the bench. He won’t be asked to carry the Cubs’ offense, nor will he need to suddenly become a massive power hitter. He simply needs to take advantage of the opportunities that come his way. And if Chicago runs into a string of left-handed starters throughout October, those opportunities could come pretty frequently. View full article

Every postseason seems to produce an unexpected hero. Matt Shaw could be the Cubs’ candidate to fill that role this year. View full video

Image courtesy of Jeff Hanisch-Imagn Images We’re just a few short weeks away from the start of the MLB postseason. The Chicago Cubs currently hold a record of 81-66. Barring a catastrophic collapse over the final 15 games, they’ll be a playoff team. With the Brewers leading the NL Central by 10 games, though, Chicago will once again have to make its way through the Wild Card round. The Cubs were in that position last year, and they found success against the San Diego Padres. Chicago took two of three games in the series, and its pitching staff played a major role in getting the job done. They didn’t allow more than three runs in any of the three games. Their NLDS matchup with Milwaukee was a different story, as two of the three games Chicago lost in that series came when its pitching staff struggled to keep Milwaukee's offense in check. If the Cubs are going to make a deep run this time, their staff will have to be at its best. So what might Chicago’s postseason rotation actually look like? For starters, I think a lot of it depends on who the Cubs draw in the first round. If Chicago gets matched up with a team like the Philadelphia Phillies, Shota Imanaga and Matthew Boyd are probably going to be huge factors. The Phillies have plenty of powerful left-handed bats, including Kyle Schwarber and Bryce Harper, and Chicago could look to play those matchups as much as possible. In that scenario, we could see Boyd get the ball in Game 1, followed by Kevin Gausman in Game 2. That would put Gausman between the two lefties and give the Cubs a veteran right-hander in what could be an elimination game. Then, if necessary, Imanaga could take the ball in Game 3. The same can probably be said if the Cubs end up matched up with the Braves. A lineup featuring Michael Harris II, Matt Olson and Drake Baldwin as three of its top four hitters is not something any pitching staff should take lightly. Atlanta has the kind of left-handed talent that could make Boyd, Imanaga and David Peterson especially valuable, and I think playing the matchups as aggressively as possible would be the right move. It wouldn’t shock me if Gausman got pushed all the way to Game 3 in that situation. That would be an unconventional decision. Gausman is arguably the biggest name in Chicago’s rotation, and Clay Holmes has looked the best out of that group in recent weeks. That said, the postseason is all about winning the matchup in front of you. If the Cubs believe Boyd, Imanaga and/or Peterson give them a better chance against a particular lineup, there’s no reason not to lean into that. If the playoffs were to start today, Chicago would be taking on the Phillies. A lot can obviously happen between now and the end of the regular season, and the Wild Card standings can change quickly, but Philadelphia appears to be one of the more likely first-round opponents for the Cubs at the moment. If that matchup does end up happening, don't be surprised to see Chicago take a left-handed-heavy approach with its rotation. Gausman and Holmes could be starters, but hand off quickly to Peterson or Imanaga—or vice-versa, But that’s far from a sure thing. The Diamondbacks and Padres are both fighting for Wild Card positioning as well, and those lineups present a much different challenge. Both teams have plenty of dangerous right-handed bats, which could change how Chicago decides to construct its rotation. Against those teams, Gausman and Holmes would surely start Games 1 and 2, unless the team has to scramble just to reach the postseason and loses the ability to select their starters for those games. Should the Cubs make it out of the Wild Card round, I think they would rapidly switch to a more traditional rotation featuring Gausman, Boyd, Imanaga and Holmes. The order could obviously change depending on the opponent, but those four would give Chicago plenty of different looks. They'd need the length those four can provide to get through a five-game series. Gausman brings veteran experience and strikeout stuff. Boyd, Imanaga and Peterson give the Cubs two left-handed options who could be especially valuable against certain opponents, while Holmes is arguably the most versatile and high-ceiling (but also among the most volatile). The Cubs were aggressive at the deadline because they knew improving the rotation could be the difference between simply reaching the postseason and making a legitimate run once they got there. Now, with October almost here, they have the opportunity to use that depth in whatever way makes the most sense. Now, they have to hope that by the end of Game 162, there's any configuration that makes any at all. View full article

Image courtesy of © Mark Hoffman/Milwaukee Journal Sentinel / USA TODAY NETWORK via Imagn Images Hard as it is to believe, the 2026 MLB campaign is coming to an end. The Chicago Cubs currently sit with a record of 81-64, meaning they only have 17 games remaining on their regular-season schedule. But despite the fact that October is right around the corner, there are still some very notable games left that all Cubs fans need to tune into. Some will impact the standings, while others will give Chicago a chance to measure itself against potential playoff opponents. Either way, these contests will determine the North Siders' aptitude ahead of the postseason. Ranking Cubs' Most Important Games Down the Stretch #5: September 22nd vs. Miami Marlins The Marlins are quietly hanging around in the mix for the final National League Wild Card spot, and since we’re still a couple of weeks away from this matchup, that makes it far too early to know exactly where Miami will sit in the standings. But regardless, this is going to be a good test for the Cubs before the postseason begins. The Marlins have some legitimate talent on their roster, particularly in their starting rotation. Guys like Sandy Alcántara and Eury Pérez are capable of completely taking over a game, and while it’s too early to know who will be pitching for either side, the Cubs could very easily find themselves facing one of Miami’s top arms. This game is also the first of a series, and getting it started with a win would go a long way. Especially this late in the season, every series against a playoff-caliber opponent feels important. And with the postseason right around the corner, this one has a chance to feel like October baseball. #4: September 25th at Boston Red Sox Boston is all but guaranteed a Wild Card spot in the American League and will be the last team the Cubs play during the regular season. The Red Sox have also been arguably one of the hottest teams in baseball throughout the second half, making this a very interesting series for Chicago. It’s the same thing I just said about the Marlins game—this one is going to feel like postseason baseball, only with the atmosphere of an electric Boston crowd. The Cubs will be playing at Fenway Park in what should be a hostile environment, and winning games on the road against quality teams is something they’re going to have to be able to do if they want to make a deep playoff run. Obviously, the Cubs won’t face the Red Sox again unless they reach the World Series. But that almost makes this series even more interesting. The regular season will be coming to an end; both teams will already be thinking about October, and the Cubs will have one final opportunity to test themselves against another legitimate playoff team before the games REALLY start to matter. #3: Wednesday (Sept. 9) at Milwaukee Brewers Not only are these two playoff teams. Not only are they division rivals. This is going to be a postseason pitching matchup. Kevin Gausman will take the mound for Chicago against Logan Henderson for Milwaukee, creating a really fun duel between two very different types of pitchers. Henderson has been a breakout for the Brewers as a rookie, establishing himself as another important piece of Milwaukee’s pitching staff. Meanwhile, the Cubs traded for Gausman specifically for games like this. Chicago didn’t bring him in just to help them beat struggling teams in August and September. They acquired him because they believed he could take the ball in big games and pitch like a frontline starter. And while this isn’t technically a playoff game, it might as well feel like one. The Cubs, I’m sure, would also love to have this game after Monday’s loss. There’s still plenty of baseball left to play, but bouncing back against a division rival and a quality starting pitcher would be a good sign for a team looking to build momentum heading into October. #2: Tuesday (Sept. 8 at Milwaukee Brewers) It’s game two of three between the Cubs and Brewers in Milwaukee, and this matchup is going to be a massive test for Chicago. David Peterson will take the mound for the Cubs, facing off against the virtual lock for the National League Cy Young Award in Jacob Misiorowski. And not to mention—it’s against their division rival currently sitting atop the NL Central. The Cubs currently sit eight games behind Milwaukee and likely won’t overtake them before the end of the season. So, this game isn’t necessarily about catching the Brewers in the standings. Rather, games like this show you what a team is made of; if the Cubs want to make a deep run in October, they’re probably going to have to go through Misiorowski and the Brewers at some point. And if they do, there’s a very real chance they’ll see a matchup similar to this one. Misiorowski’s combination of dominance and a 103 MPH fastball presents a challenge unlike almost anyone else in baseball. Facing him now gives the Cubs another opportunity to see exactly what that looks like before the postseason. And more importantly, beating him would give this team a massive confidence boost. #1: September 16th vs. Atlanta Braves This game stands out for a couple of reasons. For one, the Braves are a playoff team. They currently have the lead in the NL East, but even if they don’t win the division, they’ll almost certainly find themselves in the Wild Card picture. And if they’re a Wild Card team, there’s a legitimate chance they could be facing the Cubs in the No. 4 versus No. 5 matchup. That alone makes this game important. But there’s another reason this matchup stands out. Despite the fact that neither starting pitcher has officially been announced yet, the rotation lines up for Chris Sale to start for Atlanta. And if it wasn’t for Misiorowski and his 103 MPH fastball, Sale would probably be the National League Cy Young frontrunner. Seeing high-level pitching before the playoffs is incredibly valuable, especially if the Cubs wind up seeing Sale again. He’s exactly the type of pitcher Chicago will have to beat if it wants to make a deep run, and getting an opportunity to face him at Wrigley Field before October would be a valuable experience. Just like the rest of the games I’ve mentioned, this one is going to feel like postseason baseball came early. View full article