On April 5, 2017, it was announced that Seattle Seahawks punter Jon Ryan and marketing entrepreneur Alan Miller would become part of the Pickles ownership group, along with members from Rose City Baseball LLC.

[7] Former Major League Baseball pitcher and Oregon-native Jeff Lahti took over the managerial role for the 2017 season,[8] leading the Pickles to their first playoff berth.

[17] On May 15, the Pickles announced a two-year partnership with CBD company Lazarus Naturals, the first of its kind in baseball history.

Lazarus Naturals sponsored a concert series at the stadium and provided luxury box seating for selected veterans.

[18] In December, it was announced that Rose City Baseball would operate a farm team called the Portland Gherkins for the 2020 season.

[21] The league consisted of four teams: the Pickles, Portland Gherkins, Gresham GreyWolves, and West Linn Knights.

[30] In 2023, the Pickles swept the Ridgefield Raptors in the first round of the playoffs to face the Corvallis Knights in the Divisional Championship game.

[33][34] On July 9th, Tanner Griffith, Patrick Keighran, Freddie Rodriguez, and Shay Timmer were selected to represent the Pickles in the 2024 all star game in Bellingham.

The Pickles swept the Elks 2-0 in the Divisional Series and upset the seven time defending WCL Champion Knights in Corvallis to win their first South Division Championship in franchise history.

On the very next pitch, Conner Stewart would hit a difficult to field ground ball that brought Tanner Griffith home to give the Pickles the walk off win and their first WCL Championship in franchise history.

Commissioner Rob Neyer was unable to award the Pickles the trophy for a long period of time due to fans storming the field.

[38][39] In October, the Pickles traveled to Mexico and played against Venados de Mazatlan in a friendly exhibition game in front of 16,000 people.