Part of me thinks he'd be amazing because of his skills as a captain that transfer (like knowing when to bluff), but also, it would be hilarious for him to make a big deal about finally joining them and then losing terribly because they play all the time and he never does.

The only instances that might come close I found...

TNG

All Good Things..." — Season 7, Episodes 25–26 (1994) Star Trek: Picard came to an end in a manner very familiar to fans of TNG. After closing down Guinan's bar in 24th century Los Angeles, the former crew of the USS Enterprise-D settled into a game of poker. In the TNG finale specifically, Picard finally joins the poker game for the first time, with Data dealing

Star Trek: Picard

"Remembrance" — Season 1, Episode 1 (2020) Jean-Luc Picard sits down with Data for a friendly game of poker and a spot of tea, but the showdown yields unbelievable results for the retired Admiral. This is a dream/simulation sequence set at the very start of the series. Paramount+

"The Last Generation" — Season 3 Finale (2023) The credits rolled with the lifelong friends laughing and happily talking with each other as Jean-Luc Picard dealt a fresh hand of cards at a final poker game reuniting the TNG crew — including Data (now in a new android body).

I certainly don't remember those episodes in detail, but I suspect they didn't spend a ton of time on it

Here is a trick to acting. Believe the scene. When you are in it, it is real. The more you believe that you are there in reality, the better the acting comes across. I imagine lying or bluffing in poker works the same. If I have a pair but convince myself to believe, really truly believe I've got a full house and bet and act accordingly, I can bluff better. Self deception is an art.

Sorry. My comment about him not cheating was in jest. Hence why i mentioned him cheating immediately after.