He is aided by the fact there is only one starter off the front line, so his handicap is effectively only 20m and the small field means he should settle close enough to the speed in the running line once the runners bunch.
Perhaps, more importantly, today's field doesn't have the depth of last week's Te Awamutu Cup, in which Kippenberger was a brave third after chasing all the way.
"The horses off the front line in that race were better than this week and it made it harder on us," Josh said.
"But he still went well for third and this looks a bit easier so I think he has a big chance."
Dickie rates Lively Nights a rough hope as she struggles to recapture her best after a serious injury last season.
The father-and-son training team have the erratic Sunny Vacation in today's main trot (R7) and if he produces his best he can also overcome a handicap, again aided by a smallish field.
He misbehaved at Te Awamutu but was brave winning at Alexandra Park at his previous start, with his mental attitude by far the biggest determinant of his chances.
Among his dangers is another hard-to-follow trotter in Cool Son, who was good on the grass at Hawera last start, and Meander With Pegasus, the latest trotter rejuvenated by trainer Jay Abernethy.
Earlier on the day, Dickie rates Monterey Jack (R3) his best drive after a fighting third at Cambridge just last Friday.
"He had to work just a little too hard the other day but I think he can lead and win this."
Meanwhile, champion mare Adore Me faces an interesting challenge in the $60,000 Sky City Flying Mile at Cambridge on Friday night.
While she has drawn well at barrier four she has lightning-quick beginner and freegoer Gold Ace drawn inside her at barrier two, meaning she will have to sit parked outside or come around him to win. Adore Me warmed up for the Mile by deadheating with Sky Major at the Pukekohe workouts on Saturday and if she pleases co-trainer Mark Purdon this Friday she is likely to tackle the Victoria and Hunter Cups at Melton, the first of those on January 31.
Accompanying her on that trip will be Follow The Stars, who resumes in the $20,000 Dinny Johnstone Guineas on Friday night.
He hasn't raced since bolting away with the Breeders Crown in Australia in August but easily won his workout at Pukekohe last Saturday. Under the preferential barrier draw conditions he has to start from the outside draw on Friday.
Better drawn though and certain to be a hot favourite in the $30,000 Flying Stakes is Stent.
He equalled the national mile record at Cambridge on December 24 and will start from barrier four on Friday in a race his last-start conqueror Sheemon is being allowed to miss.
