The Cubs’ final out in the 2016 World Series came off Mike Montgomery’s arm, but the road to getting him to Chicago was a little more complicated than that. At the start of that season, Montgomery was still with the Seattle Mariners, and the Cubs had to swing a mid-July trade to land the lefty reliever.
That deal cost Chicago Daniel Vogelbach and Paul Blackburn, two prospects who later each reached an All-Star level in their careers. The Cubs never seemed to lose sleep over it, though. Montgomery delivered a 3.14 ERA during the postseason run that ended with a title, and the swap also opened the door for Vogelbach to get his own shot in the big leagues.
Now Vogelbach’s baseball story has taken another twist. After a nine-year major league career that ended with 81 home runs, he’s moved into coaching, and he’s become one of the most visible members of the Brewers’ staff. This year, he helped guide Milwaukee to its first-ever title.
If you watched the Brewers’ playoff run, you probably saw Vogelbach on the top step of the dugout, cheering loudly for his team. He’s one of three hitting coaches on the staff, working under lead hitting coach Eric Theisen, and even though he’s only two years into his instructional career - he spent 2025 as a special assistant with the Pirates - he’s already made a mark.
Vogelbach has been credited with helping shape Milwaukee’s “selective aggression” approach at the plate, a plan that asks hitters to attack pitches in the zone and stay away from the ones outside it. That’s easier said than done, but the Brewers made it work better than anyone else this season, posting the best chase rate in the league at 29.1%.
The Cubs weren’t far behind. They ranked fourth at 30.4% out-of-zone swing rate, and the two clubs also finished as the highest-scoring offenses in the league.
So Vogelbach’s path from top-20 Cubs prospect to Brewers hitting coach was already unusual. The fact that he ended up helping both franchises finally break through and win a World Series makes the whole thing feel almost too strange to be real.
In Other News...
Daniel Palencia Is Suddenly A Huge Cubs Bullpen Question
Daniel Palencia entered the season with a chance to keep pushing toward the back end of the Cubs bullpen, but injuries kept interrupting that path and left him with only 32 appearances. An oblique issue and a flexor strain slowed his year, and even when he was on the mound, the results did not match what he had shown in previous seasons. The concern now is less about raw stuff than about whether he can stay available long enough to build momentum again.
Palencias split-finger pitch was a particular problem, with opponents handling it well and forcing a closer look at how he fits in late-inning roles. For the Cubs, that makes his development more than a side note, because a bullpen that needs more certainty cannot afford another arm drifting between promise and uncertainty. He still has a path back to being a trusted high-leverage reliever, but it will require better health and a more dependable third pitch to get there. [Read more 🡒]
Cubs Still Chasing The All-Star Game As Wrigley Tension Builds
The push to bring the 2027 MLB All-Star Game to Wrigley Field is already changing the blocks around the ballpark. Chicago Cubs officials and city crews are moving ahead with more than $32 million in security upgrades tied to the event, including bollards, relocated light poles and a wider sidewalk on Addison, all of it aimed at meeting league requirements before next April.
For the Cubs, the project is part of the price of hosting one of baseballs biggest showcases, with the team covering $8 million of the total. It also underscores how much work still has to be done before Wrigley can welcome the midsummer spotlight, even as the ballparks neighborhood braces for the disruption that comes with major construction and a marquee event on the horizon. [Read more 🡒]
Cubs Bring Back A Familiar Arm As Bullpen Questions Keep Growing
The Cubs have added a familiar name back into the pitching mix, signing right-hander Gabe Klobosits to a new minor league contract as they continue to sort through a bullpen picture that has only gotten more complicated. It is his second year in the organization, and the move brings back a pitcher who already knows the routine in Iowa and has spent time on both sides of affiliated baseball.
Klobosits also comes with a track record that stretches beyond the Cubs, including major league experience with the Nationals and stops in independent ball. His path has not been a straightforward one, with injuries and surgery shaping parts of his career, but Chicago is giving him another chance to work his way back into the conversation. [Read more 🡒]