Daniel Drew is a superb example of James Bard’s finest steamer portraits, incorporating signature elements from the artist’s visual lexicon such as the prominent row of waving flags and elaborate rigging. Built in 1861, the steam-powered paddleboat Daniel Drew bears the name of her first owner, an infamous Wall Street tycoon, and appears as the subject of three other portraits by James Bard. Daniel Drew was a miracle of market timing and had a unique ability to attract descriptive monikers, such as The Old Bear or Merry Old Gentleman of Wall Street, for his ability to roll up his sleeves in the rough and tumble financial markets of the day. Daniel Drew was the teflon character of his generation until the Panic of 1873 and subsequent financial reversals in 1873 bankrupted him just before the present work was painted.

In 1874, when the painting was executed, the Daniel Drew steamboat was owned by Alfred Van Santvoord, whose family operated steamboat lines on the Erie Canal and the Hudson River. According to Bard expert Anthony J. Peluso, Jr., the realistic setting shows the Newburgh Bay portion of the Hudson River near Storm King Mountain. The Daniel Drew functioned as a passenger boat serving destinations along the Hudson River like the Prospect Park Hotel in Catskill, New York, the grand establishment seen in the background. Advertising for the Prospect Park Hotel in the 1870s and 1880s highlighted the venue's "first-class music, lawn tennis, croquet" and other activities and identified the hotel's unique position in the landscape and the visitor's unsurpassed views which were to be enjoyed "in extent and beauty, and of every variety.” The 1882 advertisement for the hotel also remarked upon "The Hudson River, with its ever-changing access of busy life, and the majestic mountains in their quiet grandeur" (advertisement for the Prospect Park Hotel, Catskill, New York, June 1882, as printed in the Brooklyn Advance, June 1882). It has been suggested that the painting was commissioned by the owners of the hotel due to its prominent placement in the composition and the same level of architectural detail as the steamboat. The Prospect Park Hotel was an icon of Reconstruction Era America spotlighting a more optimistic union and the flourishing of recreation and a more hopeful future.