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Relations between the two teams started off well. The Carmel Yacht Club hired the Aptos Investigators as the staff detective 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 won the crown each season.

In Pseudo/Season 6, the Investigators and Yacht Club did not face each other during the regular season, but faced off in the Egalitarian Eight. The Aptos Investigators beat the Carmel Yacht Club in 4 games. Immediately following the loss, the Yacht Club sued for breach of contract, as they considered themselves entitled (as the paying client) to win the crown every year, including during the postseason.

In response to the Yacht Club's suit, the Investigators counter-sued claiming reckless endangerment. When the Yacht Club sued in retaliation for the counter-suit, the Investigators sued again for back pay that was owed and for emotional damages from lawsuits.

All lawsuits were dropped when the Commissioner stepped in and demanded the two teams work out their issues on the grid, instead of in the courtroom, 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 that the "Aptos Investigators Owned The Carmel Yacht Club."