Dressage Misfit:I figure I will try having someone on the ground while I'm in the saddle to reinforce my aids, and if that helps him get it
Yes, definitely do that to help him. Some horses just "don't get it" and make the connection between the ground work and the cues from the saddle. Or, if you have a very high fence or indoor arena wall (something that he's not going to consider jumping) that you could face him towards, just to eliminate the option of a forward direction and try your cues again. If you're still working by yourself, you may want to place a pole on their side of him to help him stay straight, once he starts heading backwards.
Reinbacks are hard, so one step, even a half a step back, is a great start.
This is your OTTB, right? Reinbacks aren't usually in their repertoire! From the ground, yes. From the saddle, no.
Keep up the good work!