

The Chargers are in the middle of a near-decade-long playoff drought following another wildcard exit. The last time the Chargers won a playoff game was after the 2018 season. They reached the divisional round in January 2019.
That means, should they make it next year, it’ll be a full eight years later. Two players currently on the team played for the Chargers then. Derwin James Jr., the All-Pro, is the player the team is hoping to lock up to a long-term deal. As a rookie, James posted 105 tackles, 13 passes defended, 4 tackles for loss, and 3 interceptions. In comparison, this season he had 94 tackles and 7 passes defended.
The other player was old reliable Keenan Allen, who rejoined the team after a run with the Bears. Last time they won a postseason game, he posted 97 catches, 1196 yards, and 6 touchdowns on his way to the Pro Bowl. He also put up solid stats last year: 81 catches for 777 yards and 4 touchdowns.
The last time the Chargers won a playoff game, Philip Rivers was towards the end of his historic tenure with the team. He played only one more season for the Chargers before continuing to the Colts. Just like this year, it was the Patriots who knocked the Chargers out of the playoffs that time with a 41-28 victory. Rivers was hoping for a last hurrah with the team, but now they have a quarterback not yet in his prime with all the talent in the world.
Rivers had 5 playoff wins for the team, including 14 touchdown passes in 11 total games. He also famously played an AFC championship game with a torn ACL and meniscus versus the Patriots. This was following the 2007 season. Justin Herbert showed off a similar degree of toughness battling through a broken hand this year. He hasn't had a signature playoff moment, though, at least not a positive one.
Comparing output in their first six seasons, Herbert has almost 6000 more passing yards. Rivers, of course, played behind Drew Brees for two years. Rivers, on the other hand, has a mark of leading the team to four AFC West titles after his sixth season in the league.
Everyone involved with the Chargers organization wants to see Herbert have just as long and illustrious a career in the Chargers colors. They got him a great coach and a great offensive coordinator. Once the offensive line is healed, it will be on him to deliver.