4. Trent Brown
This is undoubtedly a risky move for the LA Chargers but it could have the highest immediate ceiling of any player on this list. At his best, Trent Brown is one of the best right tackles in the entire sport and if that version of him showed up then Justin Herbert would probably have the best tackle combination of any quarterback in the league.
However, Brown has struggled in the past to stay healthy and there is also the risk of him doing exactly what Bryan Bulaga did and not play much. If the Chargers were not coming off of such a bad experience with Bulaga then it would be more likely that they take a chance on Brown.
Tom Telesco has brought in old players with injury history in the past and if the price is low enough then the Bolts very well could make the move. PFF projects Brown to get a two-year, $20 million contract. While $10 million is a lot, there would likely be very little risk in this contract and might be something the Chargers would be interested in.
That is especially true if the Chargers are not high on any of the free-agent tackles nor the potential prospects in the first two rounds of the draft. The team could look to essentially replace Bulaga's salary with Brown's and hope he stays healthy, trusting in the team's depth if not.
This does not happen if there is a cheaper free agent or early draft prospect that the team loves. If not, the Bolts may take the risk and hope it pans out.