The Sly 1 racing minigames are funny in hindsight, because I’m pretty sure they’re only time the Cooper Gang competes in contests without cheating. In Sly 2 & 3, Bentley always just has the gang sabotage their competitors [the lumberjack games, the holland plane competition, etc.]
Crack Headcanon: this is because the van minigames are planned solely between Sly and Murray, who are both too honorable.
Murray: “These dogs want me to race them three times around a track for a key :(.”
Sly: “here’s my strategy: get in there and drive your best! It's all you man. Drive the van with the left analog stick, and if you manage to pick up any nitro power-ups, you can get a boost by pressing the square button. Go get 'em! I’m sure you can win this and prove you’re truly and fairly the better driver.”
Bentley if he were involved: “slash their tires”
