The Chargers said they agreed to terms with offensive lineman Trey Pipkins III on a two-year, $10-million contract extension only hours before NFL free agency officially began Wednesday. The deal ties Pipkins to the Chargers for his eighth and ninth seasons in the NFL.
Pipkins has played both guard and tackle positions since the Chargers selected him in the third round of the 2019 draft from the University of Sioux Falls. He was expected to be a backup tackle last season, but started at right tackle after a season-ending injury to Joe Alt.
The 29-year-old Pipkins played in 13 games last season, starting 10. He started 15 games as a right guard in the 2024 season. He played all 17 games as a tackle in 2023 and started 14 games as a tackle in 2022, his first full season as a starter after playing a reserve role in his first three years.
Strengthening the offensive line was a priority for the Chargers after quarterback Justin Herbert was sacked a career-high 54 times during the 2025 season. Alt and left tackle Rashawn Slater, who sustained a season-ending knee injury, are expected to be sound to start next season.
The Chargers have won 11 games and advanced to the AFC playoffs in each of Jim Harbaugh’s two seasons as their head coach. However, they lost this past postseason to the New England Patriots and also to the Houston Texans in the 2024 playoffs in lackluster fashion.
In addition to agreeing to an extension with Pipkins, the Chargers also agreed to a one-year extension with guard/tackle Trevor Penning. They also struck deals with former Miami Dolphins tackle Cole Strange for two years and ex-Washington Commanders center Tyler Biadasz for three.
It’s also anticipated that the Chargers will seek additional help on their offensive line via the draft next month. The Chargers have the 22nd overall selection, and many mock drafts have them selecting Penn State offensive lineman Olaivabega Ioane, assuming he hasn’t been taken already.
The Chargers also reportedly agreed with linebacker Del’Shawn Phillips on a two-year, $7.5 million extension. Phillips was one of the key players on the Chargers’ special teams unit, recording a team-leading 24 tackles. He had another 13 tackles with one sack as a linebacker.