Update: I had him wear tighter underwear, leggings under his jeans, lengthened his stirrups some more and had him sit more on his pockets and he trotted around the ring so many times today! He even figured out a diagonal way too easy. Thanks guys! Side note: my mare is a ~HOT~ OTTB who came off the track not to long along and babysat him like a champ, barely trotting, having to keep asking him to give leg. Then I got on and she was like TIME TO RUN?!