2008 was the first year of the Kitsap County Bears and splitting players with the West Sound Saints in the same league didn't bode well as the team struggled through a 3-7 season.  Don Purser was a longtime West Sound Orcas and Olympic Peninsula Eagles quarterback before becoming involved in building the Bears.

Moving to the spring/summer league of the Cascade Football League proved a better choice as the team found it's winning ways.  Former University of Puget Sound record-holding back Rory Lee joined the Bears after a 2008 season with the South Sound Shockers, Lee showed his versatility as a First-Team selection at linebacker.  An unexpected first round exit from the playoffs at the hands of the Tacoma Warriors ended the Bears season.  The Warriors had lost by 28 to the Bears the previous week.

As a last minute addition to the season, the Bears accepted an offer to fill a date for the Bellingham Bulldogs vacated by the Langley Longhorns.  The Bears were unable to gather all of their players and were demolished 43-7.  Regrouping for a bowl game in Las Vegas, the Bears completed a 10-win season defeating the East Las Vegas Cobras 32-6.

2010 was a return to the North American Football League Northwest Division and started slow with the Bears trailing the Umpqua Valley Knights 6-0 at halftime of the Border War.  The team got on track against the Olympic Peninsula Eagles dominating the area rivals 39-0 and then got a much needed jump beating the Southern Oregon Renegades, a team many expected to go undefeated in 2010.  The remainder of the season was a see-saw win a few, lose a few including three losses to eventual Champion Bellingham.

Joining the inaugural class of the Pacific Football League for 2011, the Bears were the beneficiary of the temporary shut down of the Seattle Stallions undefeated championship team from 2010.  Key additions like EJ Ash, Dion Alexander, Drew Jenkins and others brought a run to 10-0 until the undefeated season was derailed by South King County.  Kitsap would avenge the loss in the PFL playoffs winning the North division title and meeting the Southern Oregon Renegades for the inaugural PFL Championship.  Taking half a squad to Lake Tahoe, California in August, the Bears found out the hard way, traveling 12 hours and missing key players to play in bowl games isn't wise, the Pacifica Islanders drubbed Kitsap 43-12 in the Tahoe Bowl finishing the season 13-2.  Jenkins would be named defensive regional player of the year as he picked of 13 passes on the season, tied for second in the Northwest at the time.  Nine players earned all-region honors and eight earned slots on Pacific League all-league teams.

Following the loss to the Islanders, Purser and the Bears shut down operations for the 2012 season.  Joe Disney was elected to the Commissioners position with the PFL.
After a year away, Purser brought the Bears back to the PFL.  The venture was short lived as the Bears struggled to attract the players necessary to be competitive in the Pacific League, limping to a 1-9 record.

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