The Los Angeles Chargers could look like a completely new team in 2024, especially considering their cap room situation. As it stands right now, the Bolts are about $40 million over the cap and are near the bottom of the league in terms of wiggle room. 

Whoever is hired as the next general manager of the team will need to figure out which players will be willing to restructure their contracts or take a pay cut to remain with the team. There are some significant free-agent decisions to make as well.

That said, here are the top 10 most expensive contracts for Chargers players heading into the 2024 season. 

10. OT Rashawn Slater

Cap Hit: $5,291,923

Analysis: Rashawn Slater was the Chargers' #1 pick in the 2021 draft. While he secured a Pro Bowl nod in his rookie year, he would end up on IR for the entire 2022 season. 

Slater ruptured his left biceps tendon ending his season after Week 3. Slater proved that he can be a force when healthy, but losing an entire season is worrisome. Slater is a highly-rated OL, but the Chargers should think about potentially asking Slater to restructure his deal as a signing bonus. 

9. OT Trey Pipkins

Cap hit: $8,750,000

Analysis: Offensive tackle Trey Pipkins signed a three-year $21.25 million deal back in March 2023. Pipkins was a high priority for the Chargers in 2023, and they landed him. 

However, Pipkins has only played one full season, which was the 2023 season. Considering Pipkins is not viewed as a top-level tackle, he could be viewed as someone the Chargers would ask to take a pay cut. 

8. LB Eric Kendricks

Cap hit: $9,250,000

Analysis: Linebacker Eric Kendricks was brought over from the Minnesota Vikings to be a premiere linebacker for the Chargers defense, securing a two-year $13.25 million dollar contract. Kendricks secured 3.5 sacks, which is a half sack away from his best of 4 during his rookie year. 

He secured 117 total tackles, which places him near the bottom in terms of linebackers. Kendricks is a bit of a conundrum, as his sack count is not terrible. However, his overall tackle count is a bit concerning. 

Kendricks might be a cap room casualty come the 2024 offseason. 

7. C Corey Linsley

Cap hit: $14,100,000

Analysis: Center Corey Linsley ran into medical issues that kept him out of most of the 2023 season. Linsley would miss the final 14 games of the season due to a non-emergent heart-related medical issue. 

This issue has been severe enough that it has led to Linsley announcing he is "99% sure" he is retiring. According to The Athletic, "If Linsley retires, the Chargers would save $8.9 million in cap space, according to Over the Cap. They would incur his remaining prorated signing bonus — $5.2 million — as a dead money charge."

Linsley is not a player the Chargers have to worry about, though we imagine they will take care of him. 

6. S Justin Herbert

Cap hit: $19,345,675

Analysis: Quarterback Justin Herbert is and should be the cornerstone of this team, so the Chargers have no choice but to pay him. Herbert signed a five-year, $262.5 million deal in 2023, and the Bolts will need to build the pieces around him that make well worth that price. 

The problem is the offensive line has not been great, resulting in Herbert being knocked out of action. The Chargers could theoretically restructure his contract, but we don't see this happening. 

5. S Derwin James

Cap hit: $19,856,400

Analysis: Safety Derwin James was meant to be the star secondary player for the Chargers. The bizarre thing is that the secondary was one of the worst aspects of the team in 2024. 

According to Pro Football Reference. James allowed a 68.8% completion rate when he was thrown to by opposing quarterbacks and coupled that with a 93.7 passer rating. These stats are certainly not the best, but they aren't the worst. 

James will likely be asked to take a pay cut should he want to remain with the Chargers in the future. 

4. WR Mike Williams

Cap hit: $32,460,000

Analysis: wide receiver Mike Williams was supposed to be the perennial target for Justin Herbert, but he tore his ACL early on in the 2023 season. 

Williams had an amazing year in 2021, securing 1,146 yards and 9 TDs. This production led to a three-year $60 million contract. Sadly, his 2022 season was far less productive with 895 yards and 4 TDs. 

Williams could return to the team in 2024, but he would need to take a significant pay cut to do so. 

3. WR Keenan Allen

Cap hit: $34,717,500

Analysis: Wide receiver Keenan Allen is by far the most important person on the Chargers offense other than Justin Herbert. 

He secured 1,243 yards and 7 TDs, even after missing the final four games due to injury. Allen is approaching 32 years old and will be a significant cap hit next season. We imagine the Chargers would ask him to restructure but he may not want to. 

Allen will be one of the tougher decisions the Chargers will need to make. 

2. DL Joey Bosa

Cap hit: $36,611,666

Analysis: Defense end Joey Bosa is the anchor on defense along with Khalil Mack. Sadly, Bosa had to deal with a significant foot injury that knocked him out since Week 11. 

Bosa has missed 20 games in the last two years and that could be the deciding factor if the team decides to move on from him. They could attempt to test the water via a trade partner, but teams might be wary of bringing him aboard. 

The Chargers could cut him, but they would incur a $22 million dead cap hit. 

1. LB Khalil Mack

Cap hit: $38,517,500

Analysis: Linebacker Khalil Mack might be 32 years old, but he is playing lights out. He officially surpassed 100 sacks in his career and surpassed his career-high total sacks by bringing in 17 during the 2023 season. 

Mack has grown plenty frustrated with the fact that the Chargers are not relevant in the AFC contender conversation, but he also wants to keep playing. 

The Chargers could ask Mack to restructure his contract, but we imagine he would rather request a trade. He is well worth his value.