Inside the amazing side gig of Bears chairman George McCaskey

SYCAMORE, Ill. — Sycamore High School athletic director Chauncey Carrick saw the umpire schedule for his school’s baseball doubleheader on April 27, and he knew there would be a conflict.

One of the umpires that day would have more on his mind than calling balls and strikes. Chicago Bears chairman George McCaskey has been officiating youth sports since his football coach at Notre Dame College Prep in Niles, Illinois, asked if any players wanted to ref Pop Warner football.

About 50 years later, McCaskey was working home plate for a high school baseball game in a small town a little over an hour west of Chicago. But McCaskey had something else going on that morning: It was the third day of the NFL draft.

Carrick, who belongs to St. Mary’s Catholic Church in Sycamore, the same church the McCaskeys attend, drove over to the baseball fields and offered to keep McCaskey updated.

“I go, ‘Hey, you guys are drafting in four picks,'” Carrick said. “Want me to stick around and let you know who you get?'”

McCaskey appreciated the help. About an hour later, Carrick returned with an update, which surprised McCaskey, since the Bears entered the draft with only four picks, including two in the first round.

“He goes, ‘Not us, we’re out of picks,'” Carrick said. “I was like, ‘Well, you just traded back in.’ He immediately wanted to know who they got.”

Carrick let McCaskey know his franchise drafted Iowa punter Tory Taylor in the fourth round with pick No. 122 and Kansas defensive end Austin Booker at No. 144, after trading back into the fifth round.

McCaskey, whose family owns the Bears, is confident enough in the management team he put together, including president Kevin Warren and general manager Ryan Poles, that he doesn’t need to be involved in every transaction.

“He truly does trust the people around him… he does not micromanage,” Warren said. “It provides an environment of an even higher degree of accountability because he’s there, he’s supportive.”

McCaskey has long favored the approach of being an NFL owner who is involved in everything but football decisions. His motto is: “Mouth shut, ears and eyes open.”

Fans and critics of McCaskey and the team, however, don’t subscribe to the same philosophy.

“The No. 1 reason I officiate is I don’t get second-guessed enough in my regular job,” McCaskey said, cracking a smile.

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CARRICK, WHOSE SON Adam has the middle name Staley after the Bears mascot, opened a prayer book during Mass at St. Mary’s and found a bookmark with a Bears logo on it near a verse with the word “Bears” in it.

“Little subtle things like that stick out to me that George does,” Carrick said. “He’s not out here pumping the Bears at everybody nonstop, but if he sees [someone in Bears gear] he’ll say, ‘Hey, nice shirt.’

“If he sees someone in a Green Bay hat, he might say ‘Hey, you’ve got something on your hat.'”

McCaskey doesn’t try to draw attention to himself. In fact, some parents of opposing players don’t even realize the umpire is the chairman of one of the NFL’s charter franchises and a grandson of George “Papa Bear” Halas.

It’s a different story for those there to watch the hometown Spartans. Everyone on their side of the fence affectionately refers to the man behind the plate without mention of his famous last name.

“He’s just George,” Sycamore resident Jan Rutherford said. “He’s part of the community.”

He’s become a fixture at these youth sports fields long after his son, Conor, graduated from Sycamore 15 years ago. Many of the students whose games he umpires have known McCaskey from a young age, but every now and again, the curiosity is still there.

“Sometimes a kid will come up to me afterwards and say ‘Hey is it true? My teammate told me that your family owns the Bears,'” McCaskey said. “But again, that’s not really top of mind for them. It’s ‘Are we getting the calls?'”

It’s different in the fall. Bears fandom is part of the fabric of this community, and McCaskey has quietly distributed tickets and parking passes to parents and players heading to Soldier Field.

Mike Warren’s connection to the Bears began as a 13-year-old watching Walter Payton. Warren, who coached soccer at Sycamore and often crossed paths with McCaskey during games he officiated, then shared his passion with his son, Joey. It was a familial bond.

After Joey died in July 2021, Warren wrote McCaskey a letter, articulating the impact his family’s organization played on the relationship he had with his son.

Not long after, a letter from McCaskey arrived at Warren’s home.

“To make such a large organization come down to family values,” Warren said. “That’s how it came across to me — that this guy is just one of us.”

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QUARTERBACK CONOR McCASKEY was heading out of bounds when he was hit, but no flag was thrown.

“His mother gave me hell that night for not making the call,” George McCaskey said. He had agreed to officiate games for the Kishwaukee Youth Football League in the early 2000s instead of having games canceled because of a ref shortage.

Having his father standing behind him as the home plate umpire didn’t guarantee Conor any preferential treatment, either.

“He said, ‘I don’t get the calls when I’m a catcher, and I don’t get the calls when I’m a batter,'” McCaskey said. “He didn’t really enjoy it.”

Eventually, Conor found another way to spend time with his father on the baseball diamond. For a brief time, the younger McCaskey picked up umpiring and would call games from the field while his father called the action behind the plate.

Even as his son grew out of playing and officiating sports, George McCaskey’s commitment to his role has remained steadfast. He arrives early to games and immediately seeks out the home team coach to let him know the game will be staffed. Prior to games, he’ll introduce himself by his first name only during the coaches meeting. He’ll let catchers know that they can ask any questions that arise about how he’s calling the game, but the unwritten rule behind the plate applies: Don’t argue with the ump.

“He runs a really tight ship,” Jason Cavanaugh, the head baseball coach at Sycamore High School, said. “He’ll ask catchers if they thought he missed a pitch, but mostly he’s in control of the game.

“It’s a legitimate strike zone. With a lot of umpires, you don’t know if a pitch a foot outside is going to be a strike or bouncing in there, but he knows where the strike zone is and he calls it.”

McCaskey takes pride in getting these calls right, because he understands a call that goes against a young athlete can be heartbreaking.

“You know how important it is to the kids, so you want to get it right,” he said. “You don’t want the kid to go home and say we could have won except for the ref.”

That happened once, and it’s a moment McCaskey remembers as one he’d like to have back. While a student at Arizona State University in the late 1970s, McCaskey and Randy Nussbaum, one of his regular umpiring partners, were part of a two-man crew calling a game at Scottsdale High School. After the leadoff batter crushed a potential triple, a bang-bang play took place at third base.

Neither McCaskey nor Nussbaum were close enough to the action to give a definitive judgment.

“He looked at me, and I looked at him, and he just made the safe signal,” McCaskey said. “The coach came flying out of the dugout because he knew we had screwed up.”

Kevin Warren believes McCaskey’s attention to detail and thoughtfulness help make him an “excellent official.”

“He’s passionate about the importance of letting the players dictate the outcome of a game and not having officiating get in the way,” Warren said.

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McCASKEY’S INVOLVEMENT IN youth sports stems, in part, from a desire to bring along the next generation. While youth sports involvement continues to grow, the shortage of officials concerns the Bears’ chairman.

“A lot of it’s because of the criticism that officials in all sports have been in,” he said. “A lot of guys are just deciding that it’s not worth it.”

Before the Illinois High School Association placed the responsibility of ejecting spectators on a third-party game administrator — often the home team’s athletic director — instead of the umpire, McCaskey had to step in when parents — or players — went too far.

“One time I kicked a shortstop out of a game,” he said. “That’s hard to do.”

Tyler Grimm, 23, has been umpiring for the past six years and is among the youngest in rotation in Sycamore. After growing up with McCaskey calling his baseball games, Grimm shared the field with the Bears’ chairman for a varsity doubleheader on May 16.

“We had a play where if you go out to see the ball out in right field, you’re supposed to stay out,” Grimm said. “He wanted me to take just a few more steps so that way if he calls the play at first base, I’m not in his way. Or that a coach isn’t going to yell that this guy is closer to it, he should be making the call even though I’m out in the outfield.”

Beginning this fall, the Illinois High School Association will recognize girls’ flag football as a sanctioned sport. McCaskey and the Bears’ organization were instrumental in pushing state athletic directors to give the sport the same resources that tackle football has long had throughout the state. Unfortunately, the lack of officials remains the IHSA’s chief concern.

“I’m thinking of signing up,” McCaskey said.

And if he does, some will react the same way Mike Warren did when he first learned who was officiating the American Youth Soccer Organization game he was watching. It starts with surprise and ends with respect.

“Frankly, it was kind of shocking when I knew he was reffing AYSO games,” Warren said. “I’m thinking to myself, why is George McCaskey reffing?

“I don’t think you’re going to find many NFL owners doing what he does.”