COLUMBIA, Mo. — Caleb Flagg’s games came first.
Playing sports as a kid, he’d wrap up his game and head over to a different field to watch another, where his older brother, Corey Jr., would be playing.
“I used to wish to be on the field with him,†Caleb told the Post-Dispatch, thinking about “all the plays we could have been making. Of course, I used to be saying to myself: I would have more touchdowns.â€
A decade and a half later, through circumstances that range from a Texas high school football dynasty to a former Missouri coach to the transfer portal, Corey and Caleb Flagg are finally on the field together.
It happens to be at Mizzou. And it was a long time coming.
Both Flagg brothers have found roles with the No. 6 Tigers. Corey, 22, is one of two middle linebackers used in MU’s defense. Caleb, 20, leveraged a strong spring camp into a rotational spot as a safety.
They transferred together over the offseason, albeit from separate schools. Corey appeared in more than 40 games across four seasons at Miami, while Caleb was ready to move up a level after two strong years at Houston Christian.
“I just can’t thank Coach Drink(witz) enough for allowing me and my brother to be a part of this,†Corey said after Missouri’s season-opening win over Murray State.
‘We know this is not normal’
Jon Kay saw both Flagg brothers coming through the pipeline.
Kay, as the head coach at Galena Park North Shore High School in the Houston area, was aware of talented brothers who were playing at Cunningham Middle School within the district.
Corey, as the elder sibling, joined the program first. He emerged as a standout during his junior year when the Mustangs marched all the way to the 2018 Texas Class 6A D1 championship game — a high school football gauntlet up there with the toughest anywhere in the nation.
North Shore won in Hollywood movie fashion, on a final-play Hail Mary pass, beating Duncanville and future Mizzou cornerback Ennis Rakestraw Jr. But Corey had struggled.
“He was trying so hard to make every play,†said Kay, now the linebackers coach at Rice. “I think it was a pretty valuable lesson for him, just to learn how to play within a defense.â€
A year later, Corey had improved. In a title game reprise, he helped the Mustangs pitch a second-half shutout for back-to-back championships to close out his career. Corey was the game’s defensive MVP.
Caleb, a sophomore at the time, was supposed to be part of that team. He’d earned a special teams role with North Shore’s varsity team, but an early season injury kept him off the field.
And Corey was off to Miami to start his college career.
“That was very special,†Caleb remembers thinking. “It really gave me hope, to see that there’s actually offers and it was real close to me. He helped me keep my dream alive with becoming a Division I athlete. ... That’s why I’m blessed to have a big brother like him.â€
But it was also a window to share the field closed.
“I always felt, even though they never told me this, that they always wanted to play together again,†Kay said.
The Flagg brothers figured the college recruiting process would put them at different schools, so that goal was on hold.
“But (in the) NFL, we had dreams,†Caleb said. “We’d see each other in the NFL, hope we get drafted on the same team.â€
Before any of that could happen, the younger Flagg had a high school career to close out. In his first season without his older brother around the house, Caleb and the Mustangs lost in the state semifinals. In 2021, his senior season, they won the championship again.
It was the third in four seasons for North Shore and the Flagg family. A video from that day shows Corey on the sideline, filming his younger brother’s celebrations.
A month later, Caleb committed to Houston Christian.
“Proud of you bro!†Corey wrote on X, formerly Twitter, following his younger brother’s commitment. “You don’t know how much this means to me, man. Love you.â€
The brothers had made it, in one sense: They were both playing college football. They also made it challenging for their family to watch them play.
“It’s still crazy how they did it, but they did,†Caleb said. “Every weekend, they split it up. ... There was always somebody in the stands for us.â€
When they could, the Flagg brothers watched each other’s games. At its most convenient, it was a bit like their youth sports days — one would play before the other, making cheering each other on a pre- or postgame activity.
“If we had a 6 p.m. kickoff and he had a 2:30,†Caleb explained, “pregame, I’d have his game on my phone, watching his game. Watching him would kind of get me in the mode for my game.â€
After the 2023 season, Corey decided to transfer for his final year of college football, while Caleb wanted to jump up a level or two after a strong performance at Houston Christian, so the brothers entered the transfer portal.
Blake Baker, at the time Missouri’s defensive coordinator, called Corey. Baker had recruited the elder Flagg brother to Miami, back when he was the Hurricanes’ defensive coordinator and linebacker coach.
And after the Mizzou assistant saw some of Caleb’s film, he had a question for Corey: Would both brothers want to play for the Tigers?
“That was a blessing that just fell in our lap,†Caleb said. “It didn’t build up — nothing to it. It was just straight like that.
“We instantly knew that we wanted to play together, so that decision was instantly made,†he continued. “But once we got up here to the visit to Mizzou, man.â€
Both brothers were impressed with what Missouri had to offer. On their visit, they clicked with Daniel and Harold Blood, another pair of brothers now together with the Tigers after the latter’s offseason transfer.
Almost immediately after the Flaggs committed to MU out of the transfer portal, there was a speed bump. Baker suddenly left to take the defensive coordinator position at Louisiana State. The coach who’d drawn both brothers to Columbia was gone.
“All well wishes to Coach Baker,†Corey said. “He’d done a lot for my family, even when I was at Miami, so I appreciate him for what he’s done. Definitely was some uncertainty because that was the guy I was talking to in the portal process — him and (linebackers) Coach DJ (Smith). But Coach DJ and Coach Drink made us feel at home, so that’s why we stayed.â€
As Drinkwitz remembers it, he didn’t have to do any real convincing to keep Corey and, by extension, Caleb in the program.
“Honestly, there really wasn’t a pitch,†Drinkwitz said. “(Corey) chose his place. Coach Baker had a lot to do with it, obviously with the previous relationship and knowing the scheme. But he chose this place for the guys in the locker room and has reiterated that throughout the process: that this was a place for him and his brother.â€
What helped keep the brothers on board, too, was consistent delivery from the Mizzou coaching staff. Promises were kept, even if the coach who made them was no longer in the facility.
“Everything they said they would do, they’ve done,†Corey said. “They’ve provided this opportunity to compete.â€
And compete they did. Caleb was the Tigers’ spring game defensive MVP, a performance that positioned him well for a spot on the two-deep when preseason camp rolled around. Corey has impressed, through two games, at linebacker, where his ability to cover ground is reminiscent of his North Shore performances.
They’re enjoying having each other around. Between practices, they watch video clips together — “that’s fun, watching film with our brother,†Caleb said.
The Flagg family attended the Tigers’ first two games of the 2024 season, basking in the ease of being able to see both brothers in one game, no dividing and conquering required.
“It’s unreal, and it’s a blessing,†Caleb said. “(We’re) not taking the moments for granted because we know this is not normal. Not everybody gets to play with their brother and have your family be in one place for a football game. We’re cherishing the moments.â€
They might both be contributors to a Southeastern Conference program, but the roots of making it to this stage, together, are in growing up together.
“Growing up, I always chased my brother because that was always my role model,†Caleb said, then added: “He’s a phenomenal big brother. He gave me a perfect example to follow.â€
And following him to Missouri has worked out. Caleb is reminded of it from time to time when he’s sharing the field with Corey and sees his last name mirrored on the jersey in front of him.
“It’s still a thought in my mind,†Caleb said, “like, ‘Man, that’s my brother.’â€