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Kennedy was playing cricket for a team of Wingatui racing participants against a Taieri team in Mosgiel yesterday. Although his side faced an uphill battle after chasing leather in the field, Kennedy was able to reflect on the runs he had put up in the world of horse training, culminating in his 100th training win at Ascot Park on Saturday.
Kennedy prepared Chapel Star to win in a rating 75 sprint, giving the King's Chapel gelding his third win from his past four starts.
And it is appropriate that one of Kennedy's most loyal owners - Lindsay Parr, of Mosgiel - should get the honour of having his horse associated with an auspicious milestone.
Kennedy considers himself lucky to have owners rather than too many syndicates to deal with, and owners such as Parr and his brother, Eric, along with Fred King helped him make the switch to full-time training five years ago.
Kennedy had been training part-time for seven or eight years after finishing his career as a jockey with 353 wins.
''I got some good owners, so I thought I'd try and do a bit better,'' he said.
''[Single owners] are a dying breed really - most of them are syndicates now. I've only got one syndicate out of the whole team, so I'm lucky that way.
''A couple of the owners are semi-retired. They've got enough money and they're passionate about the game, so it's good.''
Kennedy has also struck success through horses with the Brook moniker, courtesy of Fred King, and he rates one win in particular as his most pleasing result in the 100 wins.
''I think the biggest was probably Lesley Brook winning the Welcome Stakes first up,'' he said.
''Lesley Brook is probably the best galloper I had. Mr Toff [who won six races when trained by Kennedy] was a good horse - he won a couple of hundred thousand [dollars] in Australia. There have been a few not-too-bad ones.''
King's investment in horses has worked out well for both the Mosgiel owner and Kennedy.
''He's gone and spent a lot of money and has been lucky enough to get two good fillies [Lesley Brook and Miss Millbrook],'' Kennedy said.
''A lot of people spend the money he's spent and get nothing. He's very loyal and does what is best for the horse.''
As for Chapel Star, a trip to Cromwell on March 3 could be next on the horizon - although Kennedy will be waiting with bated breath to see how his three-length win affects his rating.
''It depends what the handicapper gives him,'' he said.
''He's only a three-win horse so he shouldn't be out of the 75 grade.
''There's a 75 1400m at Cromwell, which would suit him, but the handicapper is quite hard to work out, so you're not sure what's going to happen.''