For most people, sports are more than hobbies – they’re part of our identity. This is especially true for most fans of the Chicago Cubs, each of whom have at least one story of how the iconic Midwest team has impacted their life in one way or another.

This is the story of how The Chicago Cubs helped shape one family, generation to generation, through historic losses and wins, big-time trades and up-and-comers, and how baseball kept the bloodline strong from one man’s grandfather to his 23-year-old daughter.



It all began with Dominic DeFilippo, a St. Louis native raised in the Gateway City in the early 1900s. Back then, the Cardinals and the Cubs rivalry was as heated as ever, and Dominic would race to Sportsman’s Park each time the Downstate Illinois rivalry was up for contest. He’d kick dust all the way up Elizabeth Avenue in the Italian neighborhood, The Hill, joined by two other local boys from the street: Yogi Berra and Joe Garagiola, Dominic’s classmates and two of baseball’s future greats.

From the first ball game Dominic – or Figs as Yogi and Joe would call him – watched at the old Sportsman’s Park stadium, baseball would forever be in the family’s blood, as his grandson Bob Callahan explains.

“I spent my first 7 or 8 years in Chicago in Edgewater, so about 45 minutes or so from Wrigley Field by way of the Clark Street bus. But it didn’t matter how far from The Friendly Confines I lived – I still felt the same crazy winds from Lake Michigan every morning in Edgewater as the players did on the field and I still walked home along Clark after school just like they did every night after practice. There was about as much Cubs in me as there was Cards in my grandfather when he was my age.”

Bob attended his first game in 1968 with his mother, when the San Francisco Giants visited Chicago on September 3. During that time, the Giants team was stacked with the literal giants Willie Mays, Willie McCovey, Juan Marichal and Bobby Bonds. Bob watched wide-eyed beside his mother, Josephine, and waved excitedly to the field when their Cubbies joined the field. Ernie Banks on first, Don Kessinger as shortstop, Ron Santo on third – Bob spewed off the names to his mother who knelt beside him and adjusted his cap in the warm sun of the Chicago summer.

The Cubs would go on to win that game 8 to 3, and Bob watched through the darkening afternoon as Ernie Banks belted a home run in the bottom of the 7th over the ivy onto Sheffield, bringing himself and Ron Santo round the bases to secure their six-run lead. In his mind, Bob ran right behind them, and he heard the roar of the stadium as his feet crashed into home plate.

“We all bled baseball, my dad most of all. He was a blue-collar guy, so we didn’t have a lot of money, especially for leisure or anything like that. But we needed our baseball, so, throughout 1969 and ’70, we’d go to the Sunday double-headers as you would only pay for one game. We usually stayed until the 7^th inning of the second game, depending on the score. I was actually at the doubleheader in ’69 when the Cubs were swept in both games and the Mets took over first place. My dad and I were both crushed.”

In August 1969, Chicago saw a typical late summer day the likes of which have made people of all backgrounds fall in love with the city. High 80s with a warm breeze from the lakeshore and a double-header in Wrigley Field. Bob and his father, Robert, discussed the Cubs’ starting lineup while preparing a stack of peanut butter and jelly sandwiches, which they’d bring into the stadium to munch on in lieu of buying snacks. The first game began shortly after 2pm, and father and son each punched their fists into their respective mitts with a cold Coke beside them.

Unfortunately for the loyal Cubs fans in attendance, including the Callahans Robert Sr. and Jr., they lost both games that day, and they’d eventually go on to lose the National League East to the Mets after being in first place for 155 days.

“I get emotional when I think of how Dad would get so down,” Bob says. “After almost every season, even just after some bad games, he would say he was switching over to the Sox. But of course he never could. It wasn’t the same – it wasn’t our team. He’s smiling down on us now though.”

“I continued to go to ball games throughout the ‘70s. I remember going in ’74 with some buddies. It was the first time we all went to a game on our own. I was about 11-years-old at the time. Five dollars got us there and back on the bus, a ticket to the game, a hot dog and a Coke. The ticket was for a seat in the grandstands, but you could get away with sitting in the box seats without a ticket, if no one showed up and we all behaved, of course. That’s how you do baseball in Chicago. That’s what it meant to go to a Cubs game in the summer growing up.”

The Callahans eventually moved to Peterson Woods off Lincoln and California, and Bob’s love for both baseball and music continued to grow.

“Just as he did with baseball, my grandfather set up my family with a love for music, too. He booked major talent in Chicago when he grew up, hired all the big jazz artists of the day for clubs around the city. He even owned a small jazz bar called “The Shrimp House” for a while. And my mother always had music playing in the house. When I was in fourth grade, I had a couple dollars, and called my ma to tell her I wanted to buy a record and asked if she could pitch in some money. She asked what it was, and I told her it was a Rolling Stones album, and she said okay. And when I started working when I was 14-years-old, I made about $60 a week, and spent about $45 of that on records. The music and the baseball has always been part of our blood.”

Like many people and their passions, Bob’s relationship with baseball wasn’t a one-sided obsession. It seems that baseball was as much in love with Bob as he was with the sport – everywhere he went, every job he worked, baseball inevitably wound its way into the story of his life.

“When I was working at a family-owned shop called Record Warehouse, a closer named Lee Smith was a regular customer, would come in every Sunday evening and buy tons of classic VHS tapes. I actually had his home phone number (this was before cell phones, remember). He would order stuff, I would call when it came in, even if he was out of town pitching with the team and I’d talk to his wife while watching him play on the TV in the back of the store. He even brought me a ball signed by the whole ’84 team.”

“Anyways, he was looking out for a rookie shortstop named Shawon Dunston – sort of a hothead. At one point, Lee was way back in the store and some drunk is giving Shawon a hard time in the parking lot. They start fighting, I get Lee, who comes running out. Well, this guy sees Lee who had a really dark complexion and a really bad fro, as well as being 6’6” and maybe 260 pounds. I never saw a drunk run so fast as when Lee came busting out of that store.”

When Record Warehouse was eventually purchased by a corporate company, Bob stayed all of 4 hours before quitting after his six-year stint at the local retailer, during which time he had served dozens of Cubs players who had lived on the North Side. From there, he got married in June 1987, started a gig in the warehouse of Warner Music Group and eventually built a career and family around his two passions: music and baseball.

“Years later, for work we did a presentation in downtown Chicago and our guest speaker was Ernie Banks. He spoke to our guests and then we all took a fancy coach bus to Wrigley. I got on the bus, sat down in the front row as it was one of the only seats left. Ernie got on the bus, looked around, said hello, shook my hand and asked if I minded if he sat next to me. I swear I thought he was going to break my hand. The strongest wrists on any human I have ever met! So it was about 45 minutes to the park and the two of us talked ball the whole way.”

Bob raised his family just outside the city in Mount Prospect and, as manager of Sales and Marketing for WMG’s Midwest area, set up his office in his home basement, affording him lots of time to spend with his 15-year-old twins and his oldest daughter, Sam.

“Working out of the house, I always had a relationship that many Dads don’t have with their kids. I was always the one who got them from school when they were sick, things like that. It was special, so they naturally started picking up on things that they probably wouldn’t have been so eager to adopt had I not been around so much. Baseball, of course, was one of them.”

“Whenever there was a cool promotion going on at work, especially during the summer, I would always take Sam with me. One of our retailers was a big advertiser with the Cubs, and one day, they had a day at the ballpark where the employees and their local rep were invited to the game with one of their children. At the time, Sam was only 5 or 6-years-old, but she went with me.”

“The Cubs players came out and ran drills with the kids, hitting, throwing, etc. Steve Downs was a rookie pitcher who was working with a group of kids including Sam. She was the only female, so he was really encouraging her, taking extra time, you know. We were then brought in an area for a special lunch. Steve Stone, who was the color analyst at the time, was kind enough to sign a ball for her.”

Now 23-years-old, Sam has followed in her father’s footsteps in more ways than one. She pursued her love of music, cultivated in large part by tagging along with Bob to numerous meetings with artists like Fall Out Boy and Panic At The Disco, with a job in Nashville. Additionally, she remains a diehard Cubs fan, just like the generations of Callahans before her.

“Since then, even though she lives out of state now, she always makes it back for at least one game in the summer. Like my Dad, I try to get all 3 of my kids to the ballpark at least 1 or two times per summer. Sam is actually flying home for the final two home games of the World Series next week! Even if we can’t go to the games themselves, she just wants to be here. If anything, we get to simply watch the games together, like we’ve always done.”

“One hundred years after her great-grandfather got into the music business as a baseball fan, after years of my parents taking me to the record store and the ballpark, it means everything to me to see Sam doing what she’s doing and realizing her dreams. She’s very intense like me, so it’s kind of a family joke that I tell her, ‘Yeah, you’re a Callahan.’ The music and the sports is just part of our blood.”