Five most challenging NFL offseasons 

February, 17, 2014
Feb 17
10:33
AM ET
Jerry JonesDerick E. Hingle/USA TODAY SportsJerry Jones and the Dallas Cowboys face a tough salary-cap situation this offseason.
It was June 1995 when news broke that Raiders owner Al Davis would move the team back to Oakland from Los Angeles. I'd grown up in Northern California, so the happy news stirred in my mind images of the team's rich history: Ghost to the Post, Sea of Hands, Marcus Allen knifing through the middle of the Washington defense in Super Bowl XVIII. Naively fearing a mad rush to the box office, I hastily called an old neighbor and went in on season tickets: Section 320, Row 8.

The team returned, but not the glory days. By the time the Raiders reached the Super Bowl again eight years later, I was covering the league and hadn't watched a game socially in five seasons. My fan card had expired forever, but it was for the best. The Raiders have posted an NFL-worst 53-123 record (.301) in regular-season games since that 2002 Super Bowl season. JaMarcus Russell and Darrius Heyward-Bey headlined disastrous drafts. DeAngelo Hall, Javon Walker, Kamerion Wimbley, Gibril Wilson, Richard Seymour and other veteran acquisitions produced more salary-cap headaches than on-the-field successes.

While those disappointments now appear to be in the past, as the Raiders lead the NFL in projected salary-cap space heading toward the 2014 season, challenges remain. The Raiders might have finally gotten their heads above water in relation to the cap, but from a personnel standpoint, they've surfaced at the bottom of the Grand Canyon. They have the money to make free-agent signings, but with limited options available (free agents who would want to sign in Oakland, at least), their best course of action is to rebuild over the long term. Unfortunately, their coach and general manager could need short-term results to keep their jobs. That’s a tough predicament to manage, perhaps even an impossible one.

Which other teams are facing the most difficult offseasons for 2014? Here are my picks for the five most challenging.

1. Dallas Cowboys

The Cowboys are a mess from a salary-cap standpoint, and it will affect their team-building again this offseason. For years, the organization has relieved short-term cap pains by pushing charges into the future, all in the name of a win-now philosophy. That probably will be Dallas' approach again this offseason as the team tries to clear more than $20 million just to comply with the 2014 cap as required by March 11.