John Mecray's Shamrock V (1995) is among the top lots of a sale of Maritime paintings and decorative arts at Bonhams New York on January 28.
The lot is valued at $60,000-80,000.
It depicts the Shamrock V, a J-Class yacht built in 1930 by Sir Thomas Lipton for the America's Cup challenge.
Bonhams comment: "Following her launch on 14 April 1930 she showed early promise on the British Regatta circuit winning 15 of 22 races."
Sadly it did not fare as well in its debut race in America: "The first of the best-of-seven races was a convincing victory for Enterprise winning by nearly three minutes. Shamrock V was to fare worse in the second race losing by nearly 10 minutes.
"The third race finally provided the assembled thousands on the shore at Newport, the racing they craved. Shamrock V's initial lead at the start was relinquished to Enterprise after a tacking duel.
"Following this surrender disaster struck, as Shamrock V's main halyard parted and her sail collapsed to the deck. The fourth race clinched the cup for Enterprise after which Sir Thomas Lipton was heard to utter 'I can't win'."
John Mecray is a well-known realist painter.
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