Nothing at all dodgy about it, it's called race riding and sometimes it pans out for you and sometimes it doesn't.
He's kept the horse covered up in a small field expecting or hoping that as some went on and some dropped away that the gaps would come and if the one on the rail did drop away, then he could have gone up the rail himself with a clear run. The fact he tried twice was purely because once he's in a bad position then his only other choice was to go 4 horses wide the other way to pull around them but at that stage of the race it would have been game over and he would have got even more of a slating had he done that and the one on the rail did drop away.
You can say it's just bad luck in running as on another day it would have worked out for him but you can also argue that you make your own luck. Personally I think he took a gamble that the gaps would come and when they do for jockeys they get lauded for the rides and when they don't they get slaughtered for them.
Nothing at all dodgy about it, it's called race riding and sometimes it pans out for you and sometimes it doesn't.He's kept the horse covered up in a small field expecting or hoping that as some went on and some dropped away that the gaps would come