Spoilers ahead for This Is Us Season 4, Episode 6. Randall totally hustled his fellow councilmen on the Oct. 29 episode of This Is Us, because Randall can play golf really well, but he faked that he was terrible at it. The strategy was super smart, and it was one that he learned from his father as a child. Randall's actual golf prowess wasn't clear until the end of the episode, as he tricked viewers right alongside his fellow councilmen.
The golf outing started when Randall wanted to approach one of the councilmen (played by William Allen Young) about opening a grocery store in one of the neighborhood's food deserts (meaning a place without easy access to affordable, fresh food). It was the same councilman Randall had previously bailed on twice for family emergencies, so he wasn't really up for hearing Randall out this time. But then Randall told the men he could get them in to one of the high profile golf clubs for a round.
The men jumped at the chance and invited Randall to play with them. Randall made a dumb joke about how "golf's not really my bag," as in golf bag, and the councilmen's eyes lit up, seeing Randall as an easy target for their money-based golf game. Then came the hustle.
No, Randall didn't improve halfway through the golf round in an attempt to win all the men's money. In fact, he paid out quite a bit of cash to them. He hustled them for their power, not their money. Randall played such a pathetically bad game that one of the councilmen took pity on him and gave him some tips which Randall "implemented" and suddenly improved. He made the councilman feel important and better than Randall, and soon the councilman was suggesting that Randall come by so they could talk about his grocery store proposal.
That's when viewers saw a scene where Jack was teaching young Randall golf in an attempt to make sure that Randall always fit in with the other important people at the cub — the way Jack never did. "You are going to be a very important man, Randall, and a lot of important relationships happen on a golf course," Jack told young Randall. "Sometimes you'll have to play up to the competition, sometimes you'll have to play down. But play the game."
The ensuing montage of young Randall, teen Randall, and adult Randall practicing golf confirmed that Randall had been "play[ing] down" to his fellow councilmen like his father had once coached him to do. Jack hated the game of golf, but he put that aside to help Randall learn the skills he would one day need as a man in power where still so many important conversations happen over a round of golf. (Lol, but ok.) At the end of the episode, Randall paid homage to Jack by hitting a ball in the water — Jack's specialty, since he was never very good at golf himself.
Randall often seems in over his head as a city councilor because he is brand new to this career. But he knows his way around a room — or a golf course — of powerful people and how to trick them into doing what he wants and thinking it was their idea. He may have ponied up some cash in his game against the councilmen, but he won a real seat at the city council table and is now seemingly able to affect some change. And that's what they call playing the long game.