Chess legend?

The Chess skill is hidden and separate from the Logic skill we can more readily see. Practicing and playing chess builds both skills. The next ranked member as available by phone isn't always going to be someone who has equivalent or higher skills than your sim, but that depends on the skill levels of all sims in town at the time.

There are ways to seed the town with some skilled chess players and dismiss the next ranked one so that the phone rolls up someone else to play against. This becomes important when the ranked opponent is always too busy to play, as might happen if they run a cash register most of the day or something like that. Not sure what happens when both sims end up being in the same household; you cannot summon them by phone but they should be able to play a ranked game against each other (I think).

The interventions, if they are needed and they aren't always so, require mod usage. That would be NRaas MasterController and its MC Cheats module in particular. The same kind of thing can happen with the Martial Arts opponent selections from WA.

He was finally able to challenge the family member to a game of chess. Took two tries to beat him. The next ranked person was available to invite over. Beat her fairy self. :) On to the next!

When it comes to chess it has been my experience the more your Sim 'practices' with other Sims or plays against others Sims the better they become with the game. Playing chess on the computer, I think, is more geared towards building the logic skill. I have a teen with this lifetime wish. I send her to the park on the weekends to play against other Sims because (for me) it raises three skills at one time (Logic, Charisma and Chess). When she challenges another Sim, I always host the game at my Sims home, less distractions. :)

My Sim in question hates the outdoors and has other traits that make him perfect to be a home dweller. So he hosts the games at the family mansion. He's on his way to someday be a master!