The Old Dominion Steamship Company launched Monroe at Newport News on October 18, 1902, and put her in service the following spring. She was the largest ship the line had ever owned - 366 feet long, 46 feet abeam, displacing 5,375 tons fully loaded, with six Scotch boilers driving a single triple-expansion engine and a seventeen-foot propeller that could push her at 16 knots. Her job was the Main Line Division: an eighteen-to-nineteen-hour overnight crossing between New York's Pier 26 on the North River and Norfolk, with one night aboard. Passengers boarded in the evening, ate dinner in a first-class dining room finished in white and gold with seating for 114, slept in staterooms with carved mahogany paneling and Royal Wilton carpets, and woke up at the other end of the coast. The maiden voyage left Virginia on April 6, 1903, and arrived in New York the next day. For ten years she did this run reliably.

Monroe also reflected the casual cruelties of her era. The Old Dominion Line was a Virginia company operating into a segregated South, and the ship's accommodations made the separations explicit: sixty-one staterooms on the hurricane deck and main deck for white first-class passengers; eleven staterooms on the shade deck for twenty-one first-class Black passengers, with a separate smoking room and toilets railed off from the rest of the deck. Steerage berths held seventy-eight, deck passengers fifty-three more, crew eighty-two. The Wikipedia article reports these arrangements in the period's terminology. The people housed in those segregated quarters - working people, traveling people, parents and children - had names and lives, and on the night of January 30 they faced the same dark water as everyone else aboard.

Captain Edward E. Johnson had Monroe northbound out of Norfolk; Captain Osmyn Berry had Nantucket southbound out of Boston. Both ships were running into thick fog about fifty miles east of the Virginia Capes. At roughly 2 a.m. on January 30, 1914, Nantucket struck Monroe. The damage was catastrophic. Monroe took an immediate severe list. The four port-side lifeboats could not be launched at all - the angle of the deck made it impossible. On the starboard side, boat number 1 was crushed in the collision, boat number 3 fell into the water and immediately swamped, and only boats 5 and 7 got away cleanly. Ten or twelve minutes after impact, Monroe rolled over and sank. People who were below in their staterooms had almost no time. One account describes six people trapped in a single stateroom while rescuers failed to reach them. Many crawled onto the upturned side of the hull as the ship went under, and Nantucket's boats picked some of them out of the water. Forty-one did not make it: thirty-two men, eight women, and one child; nineteen passengers and twenty-two crew.

Among those lost was Monroe's wireless operator, F. J. Kuehn of the Bronx. The wireless room was where Marconi-era operators stayed when other crew were running, because the wireless was how the ship called for help and the calls had to keep going as long as power held. Kuehn stayed at his key. He kept sending. Witnesses also reported seeing him give his life jacket to a woman passenger before the ship went under. He was twenty-something years old, doing a job that the Titanic disaster less than two years earlier had made famous and dangerous, and the choices he made in his last minutes were exactly the choices that wireless operators of that decade were quietly expected to make. Kuehn was one of forty-one names, but his is the one the story has carried.

The Steamboat Inspection Service at Philadelphia initially found both captains jointly at fault. On appeal, Captain Osmyn Berry of Nantucket was found solely guilty and his license was revoked. Old Dominion sued Merchants and Miners Steamship Company - Nantucket's owners - for one million dollars; survivors filed their own claims. Merchants and Miners invoked the Limitation of Liability Act, an old maritime statute that capped an owner's exposure at the post-casualty value of the vessel itself, and the strategy worked: Nantucket was sold at marshal's sale to the president of Merchants and Miners for $85,000, and that was the sum available to satisfy every claim. The court-condemned Carley liferafts that Monroe still carried - condemned for coastwise service on December 31, 1913, with a 90-day extension that had not yet expired - had not saved a single life. The Revenue Cutter USRC Onondaga later worked the wreck down to nine fathoms of clearance so other ships could pass safely over. Forty-one people remained where they had drowned.