It’s not every day that we see an NFL team owner officiating a high school baseball game. Something similar happened recently between the Batavia Bulldogs and the Kaneland Knights in a baseball game. Bears owner George McCaskey was seen bringing out his umpiring attire and hitting a baseball diamond. While that surely sounds unique and surprising, for those who know, McCaskey officiating a baseball game is like traveling through a time machine to the past.

“Bears owner George McCaskey is umpiring Kaneland vs. Batavia baseball right now. Imagine arguing a call with him,” a fan known as Sloche shared via X.

George McCaskey is currently the chairman of the Chicago Bears. He remains a key figure in the Chicago sports community. The footage shows McCaskey entering the field in the usual umpiring attire, sparking attention in a non-conference match-up. However, it is not the first time.

McCaskey has been calling balls and strikes for 50 years, dating back to his time as a student at Arizona State University in the late 1970s. For example, in the early 2000s, McCaskey stepped up to officiate Kishwaukee Youth Football games to prevent cancellations due to a referee shortage. He also called games where his son, Conor, was playing, and the two even occasionally traded duties, with Conor umpiring the field while George called balls and strikes behind the plate.

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“One time, I kicked a shortstop out of a game. That’s hard to do,” McCaskey said in the ESPN article. So, don’t consider McCaskey as another busy chairperson who’s just hitting a baseball field as leisure.

Back in 2024, during the NFL Draft, McCaskey famously missed Day 3 of Chicago’s selections because it conflicted with his commitment to umpire a doubleheader at Sycamore High School in Illinois. And not only in baseball, but McCaskey also officiated girls’ flag football. Last year, McCaskey, who is also a high school sports official for the IHSA and has already worked baseball games before in the past, officiated a state semifinal game.

“I’m thinking of signing up,” McCaskey said back in 2024 about officiating a girls’ flag football. So, George McCaskey, despite being associated with the NFL, is more of a prominent sports personality in Chicago. Be it in baseball, football, or any sport in Chicago, chances are high that McCaskey has some associations.

He traveled right into the 2026 season, continuing his regular high school rotation without missing a beat. His umpiring stands out even more this year. The Bears just won 11 games and face massive “Super Bowl or bust” expectations under head coach Ben Johnson. Yet, the man running the team still makes time for high school baseball.

And amid all this, let’s revisit the MLB’s own examples of such cross-sports magics.

MLB has its own examples, like George McCaskey

While it is not possible for the MLB team owners to officiate a professional game due to conflicts of interest, the league still has its own set of examples. A blast from the past was Hank O’Day.

He is a legendary umpire whose career spanned 1895 to 1927, during which he called 10 World Series. Before becoming an iconic arbiter, he actually managed both the Reds and the Cubs. He was inducted into the National Baseball Hall of Fame in 2013. So, even though not simultaneously, O’Day was at both ends of the field.

Then there was Tim Hurst. He was known as one of the most colorful umpires in early baseball history. He officiated in the NL from 1891 to 1897 and the AL from 1901 to 1904. Later, he became a part-owner of the minor league St. Joseph Saints in the Western Association. So again, although Hurst has not done both together, he has had the experience of both.

There are NFL owners like Robert Kraft of the New England Patriots who is known as a baseball enthusiast. The Kansas City Chiefs’ quarterback, Patrick Mahomes, is a minor owner of the Royals in MLB. So, cross-sports examples are several, but an NFL owner officiating a baseball game is something one-of-a-kind.