Abecassis enrolled Yankee under the burgee of the Corinthian Yacht Club, founded in 1886. He secured Carl Westerfield, a past Commodore of the Corinthian and one of the most respected racing helmsmen on the Bay.

Yankee made her competitive debut in the Admissions Day Regatta of 1906 — and won. The San Francisco Call reported that Westerfield sailed a splendid race and Yankee posted the fastest time, besting the sloop Presto by two minutes and forty-seven seconds. The victory earned her the first of two McDonough Cups, donated by J. M. McDonough — a remarkable act given that McDonough himself had suffered heavy losses in the earthquake fires. The sterling silver trophies from 1906 and 1907 were produced by Shreve & Company and weighed 44 and 27 ounces respectively. In a remarkable episode decades later, these trophies were recovered from a grandson of Abecassis living in Toulon, France, who had found them in his grandfather’s basement and located the Yankee crew through the internet.

The crowning achievement came on September 15, 1907, when Yankee won the inaugural San Francisco–to–Farallon Islands ocean race — the first offshore race ever sailed from San Francisco Bay. The course ran from the Bay out through the Golden Gate, twenty-seven miles to the Farallon Islands, and back. Yankee prevailed over larger and faster competitors, including her own Stone Yard sistership Martha. The Farallones Race would run for over a century. Yankee, at one time, was said to hold the record for the return leg — having caught a perfect following swell and surfed most of the way back. (See Chapter IX for later racing.)

But Yankee’s first chapter was brief. Mrs. Abecassis, deeply shaken by the 1906 earthquake, became determined that her family should leave San Francisco. David Abecassis eventually yielded, and in 1907 he put Yankee up for sale and moved the family east — reportedly to Vermont.