The Bosses Oscar is an interesting one, not least because they clearly think a lot of him, and he could go pretty much anywhere this season. Novice Chasing aimed at the Marsh, RSA, or the NH Chase. Handicap chasing as a novice in the Plate, the Festival Chase, or the Kim Muir with careful mark management. Or he could stay over hurdles and go for the Stayers, or stay handicapping in the Coral Cup or the Pertemps. Nine different possibilities is a lot of races to specifically nail your colours to the mast for just one.
I think we need to consider that Elliott will be desperate for Festival winners this season, and looking at all the ammunition he's got, and his normal go to races, he'll have spent months plotting his horses. So given how close The Bosses Oscar went last season, I suspect he won't be able to resist aiming at a handicap of some kind. Whether it's hurdles or fences, I'm pretty much convinced that any his campaign will be all about getting a winning mark. We know his go to method of getting winners at the Festival is using graded horses as handicappers, and TBO fits the bill perfectly.
After losing some big name owners, and Gigi withdrawing, Gordon needs new owners, and he knows that Festival winners means new people will spend money with him. He can't afford a quiet Festival, or he's going to be left a long way behind by Willie, overtaken by De Bromhead, and vulnerable to the likes of Cromwell and even Emmett Mullins et al for new money spent. This season is almost more important than those when he was first finding his way, because if he doesn't make a splash he's going to go shooting down the pecking order of go to Irish trainers.
Back to where TBO will end up, Run Wild Fred is the obvious stable number one for the NH Chase, and has pretty much the perfect profile for the race, so I can't imagine either Eliott or the Moran's wanting to waste a quality Festival dart to play second fiddle to a stablemate. And will he want to take on Bob Ollinger, My Drogo, Galopin Des Champs, etc in the other two races? I don't think so. Therefore as I said above, I think a novice chase campaign would be all about his mark and getting the right one for the right race, with a switch to the NH Chase only on the cards if something happened to Run wild Fred. I also suspect if he's novice chasing he'll run in the UK at some point before the Festival to give the UK handicapper no room for adding a bunch of weight when the weights are released.
If he stays over hurdles, his campaign can only be the Stayers or the Pertemps, with no obvious reason to drop back in trip for the Coral Cup. Gordon's record in the Stayers isn't the best and would he be good enough anyway, so a return to the Pertemps would surely be the logical race, particularly as Gordon has had success with return visits previously.
As for my own position, I currently have TBO backed for the NH Chase, but I've been considering ditching the bet for a while now, but I just haven't been able to completely convince myself to do it. I think I probably will though, because the first 'season guide' or 'to follow' list that mentions him staying over hurdles will mean cashout is gone. It feels safer to back him at a shorter price later, or back him in the any race market, than to hold on and get caught.