AFFAIR. “We learn,” the story ran, “that George Law, Esq. the owner of the famous steamer Oregon has challenged the proprietors of the new steamers Bay State and Cornelius Vanderbilt [the Commodore had named his latest boat after himself, although she was properly called the C. Vanderbilt] … to make a trial of speed of these splendid steamers;… no passengers to be taken. This will be a splendid affair, and no risk run by uninterested individuals. …”

The Herald surely knew that Vanderbilt could not resist such a challenge, for if the Commodore liked to compete by means of pricing, he liked to compete by means of speed equally well. In truth Vanderbilt just liked to compete whatever the contest.

George Law was an opponent entirely worthy of the Commodore’s attention. Born in upstate New York, he had become a contractor and had built the Croton Aqueduct and its famous High Bridge over the Harlem River. He then moved into shipping, a field in which he was so successful that he enjoyed the honorific “Commodore” along with Vanderbilt. Later he was owner and promoter of the Eighth and Ninth avenue streetcar lines in New York City.

Vanderbilt rose to the bait planted in the Herald like a trout to a fly. “I observed,” wrote the Commodore in mock wonderment, “in your paper of this day, a paragraph stating that Mr. Geo. Law had challenged the Bay State and C. Vanderbilt for a race. This is the first I have heard of the challenge, nor do I believe Mr. Law authorized its publication. …" 

“Now, I say I will run the steamer C. Vanderbilt, untried as she is, against any boat afloat, to any place they name where there is sufficient water to float her, for any sum from $1,000 to $100,000.”

It was soon agreed that the Oregon and the C. Vanderbilt would race to Sing Sing (modern Ossining and even then the site of the prison) and back for $1000.

The weather was not perfect on June 1, the day of the race, being overcast and somewhat hazy, as New York often is at that time of year. But this did not stop New Yorkers from turning out in droves.

“A few minutes before eleven o’clock,” reported the Herald, “the Vanderbilt appeared off the Battery, when the Oregon left her berth, passed around her larboard side, and at four minutes before eleven o’clock, every thing being ready, the signal was given for a start, and both boats appeared to spring from their positions. The race was contested with so much spirit on both sides, that the boats kept side and side for thirty-three miles, neither one gaining a foot on the other.” At the speed the boats were traveling at—about twenty-five miles per hour, a breathtaking pace then—only the spectators who had bought passage on other steamers that accompanied the contestants

had much view of the race.

The Oregon and the C. Vanderbilt were as well-matched as their owners, the Oregon having slightly finer lines while her rival had a slightly more powerful engine. They churned along neck and neck nearly all the way to Sing Sing, but then Vanderbilt at last began to edge ahead. In response, Law poured on the power, increasing the revolutions of his paddle wheels from nineteen and one-half to twenty-two per minute. By the turning point, he had regained his advantage and was half a boat length ahead.

The turn was the critical point of any race that involved a round trip, for Hudson River steamboats, swift and gracile creatures of the water though they were—their length sometimes ten times their beam—were not adept at turning. This was not only because of the extreme ratio, but also because their twin paddle wheels could not turn at different speeds and the paddle wheels themselves were quite fragile.

There were two schools of thought about how best to manage it. One was to make a wide turn at full power, taking a mile or more to negotiate the full half-circle. The other was to reduce power and swing into a much tighter turn, in hopes of making up in the shorter distance traveled what was lost in momentum.

The Oregon was inshore of the C. Vanderbilt, and Law opted for the wide turn. He apparently thought himself far enough ahead to clear Vanderbilt, but the Commodore fouled him and caused minor damage to the Oregon ’s wheelhouse. In the confusion that followed, the C. Vanderbilt ’s engine stopped instead of merely slowing for the turn. By the time both boats were settled on the homeward course, the Oregon was two full lengths ahead and Vanderbilt was wild with fury.

Try as he might, Vanderbilt could not make up the lost time. But Law, in his turn, had also made a bad mistake in calculating how much fuel would be needed. He didn’t want to carry any more than was necessary, of course, and off Harlem, then miles north of the built-up part of the city, his bunkers were empty. The steam pressure began to drop, and Vanderbilt began to gain.

Law had spent $30,000 on the furnishings of the Oregon—a moderate fortune in the mid-nineteenth century—and they were the last word in luxury, but he didn’t hesitate to consign them to the furnaces. Berths, settees, chairs, and doors went into the flames in order to keep up steam. Vanderbilt’s last chance went up in smoke.

The Oregon, consuming herself as she came, crossed the finish line a quarter mile ahead of the outraged, sputtering Commodore.

Vanderbilt, an honorable man,

if not a particularly gracious loser, presumably paid off the bet promptly. He was to encounter Law again and again both in business and in sport. In the 1850s they competed with oceangoing ships on the Panama run until Law and his allies paid the Commodore $56,000 a month to take his boats elsewhere. Vanderbilt began operating on the Atlantic run and soon snatched the blue ribbon for the fastest crossing.

No longer personally commanding their ships, the two old commodores continued to indulge their need to cross the finish line first by taking part in the informal trotting races held most afternoons on upper Manhattan roads. To Vanderbilt’s vast irritation, Law was one of the few who could beat him regularly.

By the 1860s, railroads, which did not lend themselves easily to racing, had become the cutting edge of transportation technology, and both men moved into that business, leaving steam-boating behind. It would be the 20th century before racing and big business intersected again.