Next up in our 90-in-90 series is veteran offensive lineman Trey Pipkins!
Will the seven-year veteran find his way back into the starting lineup for the Chargers this year? Let’s take a look at his chances!
Basic Info
Height: 6’6
Weight: 307
College: Sioux Falls
Experience: 7
A native of Apple Valley, Minnesota, Pipkins starred on the offensive line for Apple Valley High School. As a junior, he helped lead his team to a 8-3 record and the school’s first appearance in the state playoffs in over 19 years. As a senior,
he blocked for a quarterback that set school records in single-season passing yards and passing touchdowns.
Pipkins stayed fairly close to home by committing to play at the University of Sioux Falls where he was a three-year starter for the Cougars. After redshirting in 2014, Pipkins saw time in 10 games while playing mainly on special teams and sparingly on the line. In those limited snaps, he managed to allow zero sacks.
As a first time starter in 2016, he got the nod for all 10 games the team played and earned his first All-NSIC honor with the second team. He repeated the postseason accolade after starting 12 games the following year, as well. In 2018, Pipkins put the cherry on top of his lengthy college career by earning not only a First-Team All-NSIC selection, but he was also voted to the AP’s Division II All-American First Team. This was the season that helped him catch the eye of NFL scouts and it earned him an invite to the East-West Shrine Game to play against some of the best talent in the country.
In March of 2019, Pipkins also became the first player from Sioux Falls to be invited to the NFL Scouting Combine and he certainly did not disappoint. At 309 pounds, he ran a 5.12 forty-yard dash and jumped 33.5 inches in the vertical which was a top mark among all offensive linemen at the event.
Following Pipkins’ selection with the 91st pick, the Chargers had no intentions of having him see the field as a rookie. However, thanks to a string of injuries, Pipkins was called upon to start three games, including the final two of the season.
During his sophomore campaign, Pipkins lost the training camp battle to Sam Tevi for the starting left tackle spot. However, with nagging injuries to right tackle Bryan Bulaga, Pipkins ended up starting five games last year, mainly at right tackle.
During the 2021 season, Pipkins lost the starting right tackle job to Storm Norton in training camp. Norton started the majority of games but Pipkins still recorded a pair of starts due to injuries to the former.
In 2022, Pipkins finally broke through to win the starting job which he held for 14 games during the regular season. A nagging MCL injury kept him out of three contests, but overall Pipkins had his best season as a pro. Following the season, the Chargers signed him to a three-year contract to keep him as the team’s starting right tackle for the foreseeable future.
In 2023, Pipkins stayed healthy and started all 17 games for the Chargers. The 2024 season brought with it a position change for Pipkins who started 15 games at right guard following the drafting of Joe Alt to hold down the right edge.
After beginning the 2025 season looking like he be the team’s swing tackle, Pipkins was forced into starting duties following injuries to both Rashawn Slater and Alt. The veteran saw starts at multiple spots, but spent most of his 10 starts that year at right tackle.
The Good
Pipkins is the longest-tenured offensive lineman on the Chargers and he’s managed to keep his value high as a versatile blocker who could play both tackle and guard spots in a pinch. He’s always been an athletic lineman and that could serve him well as a potential starter in Mike McDaniels’ outside zone scheme.
The Bad
Pipkins has always been “fine” when he’s been on the field for the Chargers, but his games where he’s been impactful have always been few and far between. After seven years with the Chargers, I believe we’ve come to what Pipkins is and will continue to be in the NFL which is a dependable backup who can be a starter when needed.
2026 Outlook
Pipkins is currently in the running for the starting left guard job, but that also happens to be a competition that features four other players in Kayode Awosika, Jake Slaughter, Trevor Penning, and Branson Taylor. Pipkins’ athletic profile should fit well, but it’s been mostly Awosika and Slaughter who have been earning reps with the first team. If Pipkins does not earn a starting job, he’d then look to earn the swing tackle role which may not be a sure-thing given Penning’s experience there for the team in 2025.
