Chargers Roster Spotlights: Trey Pipkins III, One of LA's Best Comeback Stories

Trey Pipkins III, born on September 5, 1996, played his high school football at Apple Valley (Minn.) High School, where he helped his team to the state playoffs for the first time in 19 years. Even with the team's success, and Pipkins ability as an offensive lineman, he was a zero-star recruit according to 247Sports, disallowing him to garner any interest besides his the place where he would eventually committ to, Sioux Falls.

Once at Sioux Falls, Pipkins redshirted his first year in 2014, not getting any playing time until 2015, where he did not start, but played when called upon. In 2016, Pipkins III broke out, being named All-NSIC second team, and was selected as Sioux Falls' Most Improved Player of the year. 2017 was more of the same for Pipkins III, being named All-NSIC second team once more.

In his final year with the program, Pipkins III continued his dominance at the DII level, being named team capatain among other awards listed on the Sioux Falls website: "finished third in the balloting for the Upshaw Award (DII Offensive Lineman of the Year), and was earlier named to the D2Football.com (first team), and Associated Press (first team) and the D2CCA (second team) All-American teams"

Even with this dominance, he was still a five-year college player who only ever played at the DII level. He was expected to go on Day 3 of the 2019 NFL Draft, according to multiple scouts. He ended up going in the third round of the draft to the Los Angeles Chargers, with expectations for him to play early due to the Bolts' offensive line being extremely weak.

Chargers Trey Pipkins III, OT Sioux Falls

Once with the Bolts, Pipkins III only started in 10 games across his first three seasons, showing very little promise as an NFL-caliber player. Fans often complained about his lack of pass protection ability, leading to the Bolts drafting Rashawn Slater in 2021 in hopes of replacing their failed third-round project.

Come 2022, Pipkins started 14 games and showed signs of life as an offensive tackle, giving the team reasoning to re-sign him. They agreed to a $33 million contract over the next three years, in hopes of giving QB Justin Herbert a competent OL, something that he has yet to see in his career.

In the first season of that contract, in 2023, Pipkins III started all 17 games. He was a league -average offensive lineman, with plenty of room for the Chargers to look toward a replacement. The now Jim Harbaugh-led Bolts decided that the offensive line needed an upgrade, and they selected Joe Alt to replace Pipkins III, then moved him inside to guard, where he would start 15 games in 2024.

His season at guard was quite forgettable, not adjusting very well to the position, likely due to his pad level being too high due to his taller stature. The same could be said for Mekhi Becton, who struggled in 2025 at the same guard spot.

Speaking of 2025, Pipkins reverted to his role of being the "sixth-man" type of offensive lineman, a role he excels in...until he suffers injuries of his own. It should be noted that his PFF grades below seem harsh, especially considering how well he played when compared to the players who replaced him during the 2025 season.

2025 Season Stats

13 Games Appeared
10 Starts
606 Snaps Played

47.2 Overall PFF Grade

58.0 PFF Pass Block Grade

42.7 PFF Run Block Grade

Measurables

Mockdraftable page is unavailable for Trey Pipkins III. His RAS card is below.

Trey Pipkins posted an elite #RAS at the #2019NFLCombine with great speed and explosion drills with above average agility. His bench score kept him below 9.00.

*Splits Projected* pic.twitter.com/DlevSSW5eE
— RAS.football (@MathBomb) March 1, 2019

Contract Status

"Trey Pipkins signed a 2 year, $10,000,000 contract with the Los Angeles Chargers, including $2,750,000 signing bonus, $4,575,000 guaranteed, and an average annual salary of $5,000,000. In 2026, Pipkins will earn a base salary of $1,825,000 and a signing bonus of $2,750,000, while carrying a cap hit of $3,525,000 and a dead cap value of $4,575,000." - Spotrac

Trey Pipkins III's 2026 Season Outlook

Now in 2026, Pipkins III is comfortably the sixth offensive lineman on the roster, being paid like such. He is also now in a quick-passing scheme under offensive coordinator Mike McDaniel, giving him an offense that fits his best traits rather than the slow-developing "Burger King offense" seen by Greg Roman.

The Bolts also drafted Travis Burke in the fourth round of the most recent NFL Draft, with hopes he could push Pipkins III for that third offensive tackle spot, likely doing so next season when Pipkins III's contract becomes cuttable.

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