This pair of paintings depicts an un-identified New York Yacht Club challenge race during the period between 1872 and 1875. Depicted in these storm tossed conditions are James Gordon Bennett's (1841-1918) schooner yacht Dauntless, and another yacht, probably owned by Lester Wallack (1820-1888), a prominent actor, theater owner and member of New York Yacht Club. This was the period when these two individuals were aggressively pursuing yachting, and yacht racing. Each yacht is clearly distinguished by the owner's signal flying from the truck of the mainmast.
In the first scene entitled Two Schooners Racing in Heavy Seas, we see the two schooners hard on the wind, with the leeward schooner riding over the crest of a wave under shortened sail and Dauntless to windward on the same track. The un-identified schooner in the fore ground, flying the flag of Lester Wallack, owner of the Wallack Theater which he inherited from his father, was famous for its polished productions of English plays and some new dramas, including his highly successful Rosedale (1863), in which he starred. He purchased the schooner yacht Columbia from Franklin Osgood shortly after her defense of the America's cup in 1871, and continued to campaign her for a number of years afterward. It was not unusual for someone like Wallack to charter a yacht for season or a challenge match, which may be the case in this painting, as the yacht depicted is not Columbia.
The second scene entitled Dauntless shows her chasing down Lester Wallack's yacht with a ballooner set and all men on deck trimming in the sails while on a broad reach surfing down the large seas. Dauntless, originally modeled and built as the sloop L'Hirondelle in 1866 by Forsyth & Morgan of Mystic, Connecticut for S.D. Bradford; L'Hirondelle was sold to James Gordon Bennett, the colorful publisher of the New York Herald and a member of the New York Yacht Club in the spring of 1867. He had her modified into a schooner by J.B. van Deusen shipyard, lengthening her waterline, and re-rigging her as a schooner. Renamed Dauntless, she was introduced to the New York yachting scene that same summer. Grossing 299 tons, she measured 121 feet in length with a 25 foot beam and proved a flyer from the start. At the start of the 1867 racing season, Dauntless sailed across the Atlantic to race in British waters. Three years later, in 1870, Dauntless raced Sir James Ashbury's schooner Cambria, the America's Cup challenger for that year, back across the Atlantic, from Daunt's Rock, Cork Harbour (Ireland) to Sandy Hook which preceeded the 1870 Cup match. James Ashbury won that transatlantic dash in Cambria but Dauntless was less than two hours behind him in the race that had lasted twenty-three days. In 1871, Dauntless, now as the flagship of New York Yacht Club, was chosen to defend the America's Cup against Livonia, but due to an accident before the start she was replaced by the schooner yacht Columbia. After his failure to recover the Cup in 1871, Ashbury then pitted his brand new Livonia against Dauntless in a private race which Livonia won so convincingly that it merely made Ashbury feel even more aggrieved that he had been so decisively beaten for the Cup two years in succession. James Gordon Bennett owned the schooner until 1878. In 1882 Caldwell Hart Colt (1858-1894), the son of Hartford firearms manufacturer Samuel Colt purchased Dauntless and continued to race her until his death (on board) in 1894, when she was sold to Mrs. C. L.F. Robinson of Hartford. Henry Sears leased her and remodeled her into a houseboat. In the winter of 1915, Dauntless faced her last gale at her mooring and sank to the bottom of the harbor. Mr. Sears contacted Mr. Scott of New London, who succeeded in raising Dauntless, and towed her to Scott's yard where was broken up.