"The one thing I would say about Wednesday though (Grand National Hurdles) is that he can get a bit keen so the 4200m won't be easy for him.
"But he is trained by a top horseman in Harvey (Wilson) and he has to be hard to beat in the first race on Saturday."
Bad Boy Brown has been very strong to the line in his last three starts and the likelihood of a solid tempo set up by the likes of Laekeeper suggests on a heavy11 with the long Riccarton straight, his stamina could be the crucial factor.
If Bad Boy Brown can't propel Lupton into the 150-win club he still has another shot at it in the maiden steeple with Mesmerize, although his confidence for that was dented by his last-start hurdle failure.
"He went two good races over country (steeplechases) here last season so on that form he would be a chance but he was very poor in his hurdle race last start," explains Lupton.
But while Lupton would love to win any jumping race this week, particularly the National Hurdle, his biggest windfall would come with a horse he doesn't ride or train. Well, officially anyway.
Lupton bred and owns Winter Cup hope Herengawe, who is trained by his partner Joanne Moss but when forced a bit Lupton admits it is a team effort from the couple.
After jumping up from rating 72 to open class to record back to back wins on heavy 11 tracks, Herengawe was a brave third in the Opunake Cup won by Helena Baby two weeks ago, the best form guide to today's mile in the mud.
Today's Cup favourite Rosewood outpointed him there but as the veteran of just 13 starts Herengawe has plenty of improvement in him.
"He is getting better all the time," says Lupton.
"We sent him down to Neil Ridley at Easter and he had three races at Riccarton and the trip away really helped him grow up.
"He still has a bit more to do and we realise this race might be a year too early for him.
"But he is fit and handles the wet so he has to be a chance."
Lupton bred the five-year-old from a mare, Vim, he raced with his grandmother.
"She had the family for a long time and there have been plenty of winners from it without many top horses.
"And funnily enough it hasn't really been a wet track family but this horse, being by Zed, I think that helped him in that regard."
By the clock
Key times for your racing Saturday
• 11.25am: First race at Riccarton, the Sydenham Hurdles.
• 12.10pm: First race at Te Rapa.
• 1.35pm: Koral Steeplechase, Riccarton
• 3.20pm: $100,000 Winter Cup, Riccarton.