Former Cubs prospect's strange World Series connection is hard to ignore after Brewers victory

Pop quiz! Who recorded the final out for the Chicago Cubs in the 2016 World Series?

Any fan worth their salt knows the answer to that question is Mike Montgomery -- it was the biggest out in franchise history, after all. But a tougher question might be how the Cubs acquired the left-handed reliever; remember, at the start of the 2016 season, he was a member of the Seattle Mariners' pitching staff.

It required a mid-July trade to get Montgomery to Chicago, a deal which cost the team prospects Daniel Vogelbach and Paul Blackburn, both of whom went on to earn an All-Star nod in their respective careers. That doesn't mean the Cubs regret the deal, seeing as Montgomery recorded a 3.14 ERA during that postseason run to a title. Rather, it was a mutually beneficial swap, one which got "Vogey" a chance to put his affable personality and stout stature into the MLB spotlight.

Now, after a successful nine-year big-league career that concluded with 81 homers, he's moved onto coaching. And, as luck would have it, he's become one of the faces of the Brewers' staff, helping guide the Cubs' division rival to their first-ever title this year.

Cubs and Brewers fans can both thank Daniel Vogelbach for helping break their championship droughts

If you tuned into the Brewers' recent playoff run at all, odds are you saw Vogelbach loudly cheering for his guys from the top dugout step. He's one of the Crew's three hitting coaches, working under lead hitting coach Eric Theisen.

Despite being just two years into his instructional career (he spent 2025 as a special assistant with the Pirates), Vogey has already made a lot of fans both inside and outside of Milwaukee for his coaching style. He's been credited with helping the Brewers hone their patented "selective aggression" game plan, which encourages hitters to swing away on pitches inside the zone and lay off those outside the zone.

Simple as that sounds, it's a lot easier to do in theory than practice. Yet Vogelbach found a way to translate the philosophy onto the field, as the Brewers were the best team in terms of chase rate this year (just 29.1%). For reference, the Cubs ranked fourth in that regard, with a team-wide out-of-zone swing rate of 30.4%. Not so coincidentally, they were also the two highest scoring offense in the league this year.

Vogelbach's journey from top-20 Cubs prospect to Brewers hitting coach was already an improbable one, but the fact that he somehow played a key role in both teams breaking their World Series droughts might as well earn him a Netflix documentary.

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