1988 looked to be a challenge for the Redskins well before the season started. Jay Schroeder had departed for the Raiders and George Rogers had retired, gutting the core of Gibbs' offense. RB Timmy Smith, one of the offensive stars from last year's Super Bowl, did not maintain his conditioning, and couldn't fulfill the starting RB role.

The season started out with some promise, as the Redskins opened with a 5-3 record. The inexperienced QB Mark Rypien was phased in and showed some flashes of promise as Doug Williams struggled with some nagging injuries. The absence of a strong running game and some breakdowns in the pass defense made winning difficult late in the season, especially with a schedule that included strong teams from both the NFC and the AFC. The team finished with the only losing record in Gibbs' original tenure.

The season did feature the emergence of Monk, Clark, and Ricky Sanders as a true triple threat at WR, and laid the groundwork for Rypien's development.