The past few weeks have not been kind to millionaire racehorse owner John Singleton, on or off the track.
His Cox Plate hopes for More Joyous were dashed when trainer Gai Waterhouse selected barrier 11 for the mare.
A few days later his guesthouse on the NSW Central Coast burned down and on Saturday, his Oaks hopes took a battering with Dear Demi's unlucky fourth in the Wakeful Stakes.
However, trainer Clarry Conners is confident Dear Demi can put a smile back on Singleton's face in today's Victoria Oaks (2500m) at Flemington.
The filly is the second favourite behind Wakeful winner Zydeco, who finished just behind Dear Demi when she ran second to Commanding Jewel in the Thousand Guineas.
Dear Demi had to give Zydeco 2.5kg in the Wakeful (2000m) with the pair to meet on equal weights in the Oaks.
"I was disappointed with the Wakeful because I've been waiting a long time to get her to Flemington," Conners said. "The weight turnaround of 2kg will help and the extra distance will suit.
"I have no worries on that score."
Conners trained Research and Arborea to win the Oaks in 1988 and 1993 respectively with both fillies winning the Wakeful.
"Dear Demi is a bit more delicate than those two were," Conners said.
"And she has drawn wide  again. She has had no luck with barriers and will need a good ride from Jimmy Cassidy."
Kerrin McEvoy will ride the Anthony Freedman-trained Zydeco and is keen to give his employer, Sheikh Mohammed, his first Oaks victory in Australia.
The bulk of the Dubai ruler's Darley Australian team is trained by Peter Snowden with Freedman and Guy Walter preparing small teams for the sheikh.
Walter had success at the highest level for Darley on Saturday when Appearance won the Myer Classic (1600m) for fillies and mares.
He will be in the opposing camp today, when he saddles up Zuccotto for Sandy Tait and Jill Nivison, who recently lost their champion Tie The Knot at the age of 18.
The filly is closely related to the 13-time group one winner but has yet to display his race sense, giving Hugh Bowman a torrid time when ninth, beaten five lengths in the Wakeful.
Bowman was pleased to hear a lugging bit will be used on Zuccotto.
"She laid in on the fence in the Wakeful. When I wanted her to go, she didn't know how to help me so hopefully the lugging bit will do the trick.
"She gives me the feeling she will eat up 2500m and some of the others won't, so I think it's a reasonably open race."