An operation to embed a defibrillator in May's chest had him return to race driving two months ago but tonight is the first time he and A G's White Socks will race together since that remarkable afternoon.
They face anything but at easy task, fresh up against New Zealand Cup favourite Self Assured and most of the best pacers in the South Island, but A G's White Socks has looked fit enough at recent trials to be in the money.
"Hopefully he behaves himself at the start and the pace is on and then he could be in it," May told HRNZ.
Even the fittest version of A G's White Socks might struggle to beat Self Assured who has won both his starts this campaign and the main reason he opened as long as $1.80 was because he blew the standing start last time.
"I think he will be okay," says trainer-driver Mark Purdon in reference to the standing start at Addington tonight.
"It was actually partially my fault last start because I wanted him to go a bit quick early last start and he galloped.
"But I will be careful with him the first 100m this week and I think he will be fine."
Purdon says Princess Tiffany has been the big improver in their open class team and could be the danger tonight, while last season's Cup runner-up Spankem will trial soon and resume racing next month.
Earlier in the night, the Purdon-Rasmussen stable has a two-pronged attack in the open trot with Winterfell and Enhance Your Calm against a race-hard Majestic Man.
"I am a little worried Winterfell may be half a run short cause he has only had the one start back and had an interrupted trip home from up north, so I think Majestic Man might be too fit for him."