In most cases, I'm not a fan of generalizing players that general manager Gene Smith will or won't bring in to the team based on his brief history as the head man in charge of the Jaguars. Assumptions that he only likes small school guys, team captains, seniors, collegiate production, among other beliefs are based on too small of a sample size to hold any definitive merit.
However, Smith's belief in finding character football players has extended beyond his drafts and has included every player he has acquired in free agency or waivers. Well over 100 players have come through Jacksonville in hopes of wearing a teal jersey on Sundays and not a single one of those players has been arrested or even involved in actions that could be considered concerning.
Smith has gone on record to say that he wants character guys on the Jaguars and has made it very clear with his actions that he intends to do so. For those reasons, it seems highly unlikely to me that the Jaguars would have interest in either Vincent Jackson of the Chargers or DeSean Jackson of the Eagles if they were to reach free agency.
There's always a reason that a top free agent is reaching the open market rather than staying with their original team. Wide receivers like Larry Fitzgerald of the Cardinals and Andre Johnson of the Texans have signed huge contracts with their respective teams to ensure that they never leave. Still, some high-quality players do hit the open market and teams can often take advantage.
But when players like DeSean Jackson and Vincent Jackson reach the free agency market, it's notable that one of the major reasons they will (assuming that they do, which is not assured) is because of their personal issues beyond the game of football itself.
Vincent Jackson was arrested in January of 2006 for driving under the influence, to which he pleaded guilty. Three years later in January of 2009 he was arrested for suspicion of drunken driving to which he also pleaded guilty. In January of 2010 he was cited by an officer for driving with expired tags and a suspended liscense. The final charge was the straw that broke the camel's back apparently, and earned him a three game suspension for violating the league's personal conduct policies.
Because of his legal issues the Chargers have been hesitant to give Jackson a long-term contract and could be ok with allowing the two-time Pro Bowler to reach free agency. Bear in mind that not a single player brought in by Gene Smith has been arrested while in Jacksonville or even elsewhere since leaving the Jaguars.
DeSean Jackson may not have the legal issues that Vincent Jackson does, but his attitude problems may be even worse. His 2011 season alone included him being deactivated for a game against the Cardinals for missing a special teams meeting, a $10,000 fine and a 15-yard personal foul penalty for flipping a ball at Giants defensive coordinator Perry Fewell and being deactivated for the entire fourth quarter against the Patriots.
Whether or not the Jaguars should consider allowing a character like Vincent or DeSean Jackson into Jacksonville is certainly something that can be debated. Whether or not Gene Smith would actually pull the trigger on players such as these, is a rather one-sided debate given his personnel history. As far as I'm concerned, these two players can be ruled out as candidates for the Jaguars.