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Relations between the Carmel Yacht Club and the Aptos Investigators started off well early in the Pseudo Cup. The Yacht Club hired the Investigators to be staff detectives working at the Yacht Club's golf course. From Pseudo/Season 1 through Pseudo/Season 5, the two teams had a positive working relationship, and the Carmel Yacht Club bought won the Private Eye Crown each season.

In Pseudo/Season 6, the Investigators and Yacht Club faced off in the postseason - the Egalitarian Eight. The Aptos Investigators beat the Carmel Yacht Club in 4 games. The Yacht Club, believing themselves to be entitled as the paying client to win the Private Eye Crown each year, including the postseason, were shocked, and sued for breach of contract immediately following the loss.

In response to the suit, the Investigators counter-sued claiming reckless endangerment. When the Yacht Club sued in retaliation for the counter-suit, the Investigators sued again for emotional damages from lawsuits.

All lawsuits were dropped when the Commissioner stepped in and demanded the two teams stop being a bunch of crybabies and work out their issues on the grid, and threatened to kick both teams out of the league unless they filed necessary paperwork to formalize their rivalry.

From Pseudo/Season 6 onward, the Investigators completely dominated the Yacht Club in the postseason, making them the de-facto holders of the crown. At the end of the Pseudo Cup the Aptos Investigators formed a shell company called Aptos Investigators Owned The Carmel Yacht Club LLC and were corporate sponsors of the Carmel Yacht Club charity golf tournament, so that every poster, program, billboard, flyer, and advertisement about the golf tournament contained text at the end saying "Aptos Investigators Owned The Carmel Yacht Club."