Nicholas Oakes' column, Down The Backstretch, appears each Friday in The Guardian. - ContributedCHARLOTTETOWN, P.E.I. — In one of the most famous snubs in entertainment history, Leonardo Di Caprio went 23 years between being nominated for an Oscar in 1993, and finally winning one in 2016.
MacDonald will drive Sintra for trainer Jamie Smith from Post 9 in the $100,000 Gold Cup and Saucer final, presented by Atlantic Lotto, after his younger brother, James MacDonald, drove the classy $1.5-million winner to a crushing 1:50.3 victory in Trial 2 in Charlottetown. Anthony, the oldest of the driving MacDonald brothers, began his quest in 2003 when he drove Copeland Dan and Noble Tess in trial action, but did not make final. He returned in 2006 with his own Kickin Up Dirt, failing to make the final, but was placed first in the James MacGregor consolation.
His closest moment came in the 2015 Gold Cup and Saucer final where the skies opened at 11:45 p.m. to cancel the final and move the lone race to the following afternoon. MacDonald drove the Ron Burke-trained Atta Boy Dan to finish second by a whisker to stablemate Take It Back Terry .