2. WR David Boston (seven-year, $47 million in 2003)
In AJ Smith's last-ever offseason, he signed Meachem and Gaither to two horrible deals that would ultimately seal his fate after the 2012 season. In his first-ever offseason, Smith made an even worse signing as he signed controversial wide receiver David Boston to a seven-year contract.
The Chargers having that run in the mid-to-late 2000s really masked some of the terrible moves that Smith made as a GM. He is extremely lucky that Eli Manning didn't want to be a Charger and that the previous regime drafted one of the best running backs of all time, LaDainian Tomlinson.
All the signs were there for Boston to be a horrific signing. Just from a football standpoint, Boston missed the second half of the 2002 season and finished the year with just over 500 receiving yards. The concerns off the field were even worse. Jackson was charged with a misdemeanor DUI after traces of marijuana and cocaine were found in his blood.
Yet the Chargers opened the checkbook anyway and signed the wide receiver to a seven-year contract. His off-the-field issues would continue and the Chargers eventually parted ways by trading him to the Miami Dolphins.
The Jackson signing was not as bad as the Boston signing when it happened. Fans were excited for Jackson, whereas Boston's downfall was as predictable as it comes. The Chargers are more to blame for the Boston signing blowing up than the Jackson signing blowing up.
However, at the very least, the Chargers got one productive season out of Boston as he finished the 2003 season with 880 receiving yards and seven touchdowns in only 14 games. The Chargers didn't get anything close to that with Jackson. Which leads us into our final spot.