Fr
As Colt says, you only have to win once
Considering that you've been in the loop for around 200 years (loop starts in 1963, and it's 2250 when you leave it), they must have had that confrontation hundreds, if not thousands of times
And each time, Colt decides to stay
But each time, Colt slowly realizes why he wants to break the loop, and he ends up forgetting the past, which starts it all over again.
Colt breaking the loop is inevitable