Meet The 2026 UCF Knights: Countdown To Kickoff - No. 18 Caleb Flagg and Caden Piening
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Welcome to UCF Knights on SI's countdown to kickoff!
In this series, we are going to introduce you to every single player on the 2026 UCF football roster so that you can know what to expect from them or even pinpoint the ones you want to follow throughout the coming season. We are going to go through the Knights' roster in reverse jersey-number order, with the day each player's entry is published corresponding to the number of days remaining until UCF's season-opener on Sep. 3 at 7 p.m. against Bethune-Cookman.
For this entry, we have two players with the same jersey number. So, with 18 days to go, let's meet UCF defensive back Caleb Flagg and tight end Caden Piening:
- Who is Caleb Flagg?
- What did Flagg do last season?
- What role is Flagg going to have in 2026?
- Who is Caden Piening?
- What did Piening do last season?
- What role is Piening going to have in 2026?
1. Who is Caleb Flagg?
Welcome to UCF, @Calebflagg_ ⚔️ pic.twitter.com/0ickMqrFs4
— UCF Football (@UCF_Football) January 6, 2026
Position: Defensive Back
Class: Redshirt Senior
Height/Weight: 5-foot-10 / 200 pounds
Hometown: Houston, Texas
High School: North Shore High School
Caleb Flagg entered the college football world from a North Shore High School program that was led by coach John Kay, who is now entering his second season as the defensive coordinator at Rice. He started at the FCS level at Houston Christian, where he earned seven starts as a true freshman and he played in 11 games off the bench as a sophomore before joining his older brother, linebacker Corey Flagg Jr., at Missouri.
The elder Flagg brother was a four-year player at Miami (FL) and transferred to Missouri for his final college football season. During that lone season as a Tiger, he played in all 13 games and started seven of them. As for Caleb, he came in off the bench in 11 games during that season for a total of 257 snaps.
2. What did Flagg do last season?
Flagg played in the first four games of Missouri's 2025 season, recording four tackles and breaking up two passes, before electing to opt out of the remainder of the season in order to use his redshirt, according to a Columbia Daily Tribune article from Sep. 23, 2025.
3. What role is Flagg going to have in 2026?
As a safety, Flagg is joining a group of defensive backs that is already returning the likes of Demari Henderson and Jayden Williams and also added other transfers like Ty Bartrum, TJ Branch, Matt Irwin and Kahmel Johnson.
Flagg does not have the starting experience at the FBS level that Henderson and Williams have, nor was he as decorated at the FCS level as Bartrum. However, he does have the advantage of playing experience at the FBS level over Irwin, Branch and Johnson.
Considering defensive coordinator Alex Grinch said that he was "building a defense that allows for as many guys as possible to play at a high level," Flagg seems likely to at least have some sizeable snap share in the secondary for the Knights, at least on paper. It is just going to be a matter of just how big that snap share is, which should depend on his performance in fall camp compared to Branch, Irwin and Johnson.
Thanks to his experience, Flagg is going to end up as part of Grinch's safety rotation. What's yet to be seen is just how big a part of the rotation he is going to have.
4. Who is Caden Piening?
Position: Tight End
Class: Redshirt Freshman
Height/Weight: 6-foot-5 / 245 pounds
Hometown: Cincinnati, Ohio
High School: Anderson High School
Tight end Caden Piening committed to UCF in April 2024, and despite also taking official visits to Louisville and Florida, stayed committed to the Knights and signed ahead of the 2025 season.
During his high school career, in which he played both football and basketball, a scouting report done by 247Sports' Allen Trieu said he was reminiscent of former UCF tight end Jordan Akins, who was a receiving threat for coach Scott Frost during the Knights' undefeated 2017 season.
5. What did Piening do last season?
Despite a pair of injuries, Piening still saw the field in four games in 2025, even drawing one start against North Carolina, which allowed him to use his redshirt. However, he did not record a reception.
6. What role is Piening going to have in 2026?
With All-Big 12 Honorable Mention Dylan Wade returning for his senior season, Piening is not going to be the first in line for a starting role at tight end. However, during UCF's local media day, tight ends coach Cooper Bassett said Piening was who he thought was "getting the lion's share of one reps" with Wade.
Back during spring practice, Bassett said that, while not as slippery as Wade, Piening's size brings a different strength to the table and can allow both to be used in the same offense.
So, with an injury-riddled 2025 behind him, the 2026 season does present an opportunity for Piening to begin getting involved in the offense and audition for a starting role in the future. However, even if he is not the starter, he still could have a specific role to play in the Knights' current offensive plans.
Catch up on the rest of the list below:
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Bryson Turner is a sports journalist who covers UCF Athletics. Turner has contributed to the Black and Gold Banneret, the home for UCF Athletics on SB Nation. He has called the Orlando area home since the age of 8 and received his bachelor's and master's degrees from UCF.
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