Inside story: Libertyville native Oboikowitch has spent 23 years helping Cubs behind the scenes

Libertyville native Jim Oboikowitch had an interesting rookie season with the Cubs.

Maybe rookie season is the wrong way to describe it. He was a marketing intern straight out of college in 2003.

When the Cubs faced the Marlins in the infamous Game 6 of the NLCS that year, he was assigned a specific mission — grab boxes of “NL champion” T-shirts and distribute them to front office staff.

“At the end of the seventh inning, everyone on the marketing team was told to come up to the office, and everyone had their duties,” Oboikowitch recalled. “Someone had to be ready to change the marquee. Myself and one other intern were told we have to get the T-shirts. As soon as the game ended, they wanted us to lay the shirts on the chairs of everybody in the front office.”

Every Cubs fan knows what happened during that nightmare eighth inning. At the time Oboikowitch didn't know, since he was inside the old doughnut shop building on Clark Street hoisting boxes of T-shirts.

“We walk through the office door and there's a receptionist there and she's kind of got her head sulked and was waving us back,” he said. “We didn't see what happened, we couldn't hear it. I'm so excited and she's like, 'No, we just lost the lead.'

“So we 180'd, put those shirts back and never saw them again. I think we had to ship them somewhere.”

Rough start, but Oboikowitch was fortunate enough to land a full-time job with the Cubs when his internship ended, and he's been there ever since. He started out coordinating game entertainment. About five years ago, he became director of player and alumni relations.

The 6-foot-7 former Libertyville basketball star is typically inside the clubhouse before home games, stacking charity items to be signed or pulling Ian Happ out to the field to meet a group of kids from his foundation.

During games Oboikowitch is usually in the suites, escorting former players or celebrities to greet fans. He's one of the reasons so many Cubs alumni return to Wrigley Field. Two players on the wish list who haven't made it back are Dave Kingman and Rick Reuschel, but he's trying.

“All of it's kind of a dream for me,” Oboikowitch said this week. “I laugh with some friends every now and then, because I'll be driving and get a phone call from Happ or (Anthony) Rizzo. People will be like, 'Is he really calling you?' There are a lot of, 'Is this real life?' moments.”

Winning feeling

There have been better endings during Oboikowitch's 23 years working for the Cubs — 2016, specifically.

The Cubs flew front office staff to Cleveland for the World Series games. Because his wife, April, had a work conflict, Oboikowitch decided they would drive on their own.

He watched the final out from the right-field stands, sitting near childhood friend Lukas McKnight, a scout for the Cubs at the time. Oboikowitch made a quick visit to the winning clubhouse and got to touch the World Series trophy, which was being held in the training room for safekeeping.

At that point, Cubs staffers had to hop on a bus to the airport and fly home. Oboikowitch and his wife had a hotel room and a car, so they were available to stay and celebrate.

“We ended up spending the after party of Game 7 with Chris Chelios and Eddie Vedder,” he said. “I'd gotten to know them through the Cubs and they were going to celebrate right across the street at a place called Victory Alley.

“That whole place had cleared out, because the Cleveland fans had gone home disappointed. So we ended up walking over there with them and celebrating for another hour or two.”

Sean Casey from MLB Network wandered over and joined the party, sharing insight about the Jason Heyward rain delay speech. Otherwise, it was a small celebration in a mostly empty sports bar.

“It was surreal, but it was so exciting to talk to other Cubs fans,” Oboikowitch said. “Both of those guys are so passionate about the Cubs, especially Eddie. He couldn't get over the fact that we had just won the World Series.”

Past and present

Connecting Cubs alumni with current players is one of the best parts of the job.

“I think the players really appreciate it,” Oboikowitch said. “Opening Day, Ian Happ was talking about the torpedo bat with Billy Williams. It was really a cool moment to hear them just chat for a couple minutes about it.”

As the longest-tenured current Cub, Happ has probably spent the most time around Oboikowitch.

“He appreciates what we go through,” Happ said. “He's here every day, crazy hours. There's a lot that goes on behind the scenes. What it means to make this place feel like a family and make it easier on us, he's the definition of that.”

The alumni relations category reached a pinnacle earlier this month, when Anthony Rizzo gave Oboikowitch a shoutout during the news conference to announce Rizzo would become an official Cubs ambassador.

He wasn't part of the sit-down dinner at Wrigley Field, when Rizzo worked out the details of his role with chairman Tom Ricketts and president of business operations Crane Kenney. But Oboikowitch did help get the ball rolling with Rizzo, at the direction of his bosses.

“The Rizzo moment was one of the best days I ever had at Wrigley Field,” Oboikowitch said. “To see him get that outpour from the fans, and just the love and appreciation, I think it meant a lot to him. I think it meant a lot to fans to see him back.”

Besides working for the Cubs during Rizzo's 10 years with the team, Oboikowitch has also done triathlons to helps raise money for the Anthony Rizzo Family Foundation, which helps pediatric cancer patients.

“Something about all of it was perfect when he walked out on the field with his family for the first time,” Oboikowitch said. “I was helping move him from Point A to Point B throughout. Everywhere we went, fans were going crazy. It was so cool to see.

“He was very happy with the day and said thank you. I was like, 'This was honestly one of my favorite days I've ever had here.' He was like, 'Really?'

“'Winning the World Series and the day they walked out with the trophy at the start of '17 stood out, but Riz, this was really cool.'”

Just a couple of longtime Cubs employees living the dream.