Learn Portuguese (Portugal): Cada neto costuma jogar xadrez com ele. - Each grandson usually plays chess with him.

This sentence uses the verb costumar (to be in the habit of) combined with the infinitive verb jogar (to play). Instead of using a separate adverb for "usually", Portuguese frequently uses costumar followed by an infinitive to talk about regular habits. Since cada neto is singular, we use the third-person singular form: costuma.

Why is neto in the singular if we are talking about multiple grandsons?

The word cada translates to "each" or "every". Just like in English, cada is invariable and must always be followed by a singular noun. Even though it implies a group of grandsons, grammatically you are talking about them one at a time.

Don't we need a preposition between jogar and xadrez?

You can use one, but it is not strictly required. For sports and board games, you will often hear Portuguese speakers use jogar directly followed by the game, as in jogar xadrez or jogar futebol. You might also see it written with a preposition and article, like jogar ao xadrez, which is also completely correct.

How do I pronounce the word xadrez?

The letter 'x' at the start of a Portuguese word is always pronounced with a "sh" sound, like in the English word "shoe". Additionally, the 'z' at the very end of the word also makes a "sh" sound in Portugal (unless the next word starts with a vowel), so the whole word sounds a bit like "shah-dresh".