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But 33 starts later, it was relief he felt when Matai Prince finally came home at the head of the field, holding off a late bid from Franco Ryker in a non-winners' mobile pace at Waikouaiti on Sunday.
Milne bred the Badlands Hanover gelding out of the five-win BG's Bunny mare Matai Gigi with his father, Alec, and initially thought a win would be just around the corner, especially after he qualified at Balfour in November 2009 by 5 lengths.
''I thought I had a really nice horse and then mentally, he just hasn't been able to handle racing,'' Milne said.
Matai Prince failed to place as a 3yr-old in four starts, and claimed a solitary third in six starts as a 4yr-old. The lean patch continued in his 5yr-old year as he finished third just once in 14 starts.
After eight starts for nothing as a 6yr-old, Milne decided Matai Prince needed a change, so he dropped himself from driving duties and handed the reins over to Clark Barron.
''In desperation, I had a change of driver, and it's worked the oracle on the grass,'' Milne said.
''They get used to you after a while.''
Despite the frustrating formline, Milne was pleased with what he saw at Cromwell when the gelding finished sixth behind Den Helder, and decided the grass surface was the best option, especially after two more subsequent runs out of the money on the all-weather surface.
You get the feeling Milne would have kept trying to crack Matai Prince's maiden status, even if it took another 33 starts.
''You get determined, because I knew he was good enough to win as a 3yr-old and you just keep going until you get that win,'' he said.