The Life of Phineas T. Barnum

Author: Joel Benton

Chapter IV. Trying Many Ventures.


About this time Barnum, with a Mr. Samuel Sherwood, of Bridgeport, started for Pittsburg, where they proposed to open a lottery office. On reaching New York, however, and talking over the scheme with friends, the venture was abandoned and the two men took, instead, a pleasure trip to Philadelphia. They stayed a week, at the end of which time they returned to New York, with exactly twenty-seven cents between them. Sherwood managed to borrow two dollars—enough to take him to Newark, where he had a cousin, who obligingly loaned him fifty dollars. The two friends remained in New York on the strength of their newly acquired wealth for several days, and then went home considerably richer in experience at least.

Barnum now went into the lottery business exclusively, taking his uncle, Alanson Taylor, into partnership. They established a number of agencies throughout the country, and made good profits from the sale of tickets. Several of the tickets sold by them took prizes and their office came to be considered "lucky."

The young man was prospering also in another direction. The fair tailoress smiled on him as sweetly as ever, and in the summer of 1827 they became formally engaged. In the fall Miss Hallett went "on a visit" to her uncle, Nathan Beers, in New York. A month later her lover followed, "to buy goods," and on the 8th of November, 1829, there was a wedding in the comfortable house at No. 3 Allen street. Having married at the age of nineteen, Barnum always expressed his disapproval of early marriages, although his own was a very happy one.

Returning to Bethel, Mr. and Mrs. Barnum, after boarding for a few months, moved into their own house, which was built on a three acre plat purchased from the grandfather.

The lottery business still prospered, but it was mostly in the hands of agents, in Danbury, Norwalk, Stamford and Middletown, and Barnum began to look around for some field for his individual energies. He tried travelling as a book auctioneer, but found it uncongenial and quit the business. In July, 1831, with his uncle Alanson Taylor, he opened a grocery and general store, but the venture was not particularly successful, and in the fall the partnership was dissolved, Barnum buying his uncle’s interest.

The next enterprise was an important one, it being the real beginning of Phineas T. Barnum’s public career.

In a period of strong political excitement, he wrote several communications for the Danbury weekly paper, setting forth what he conceived to be the dangers of a sectarian interference which was then apparent in political affairs. The publication of these communications was refused, and he accordingly purchased a press and types, and October 19, 1831, issued the first number of his own paper, The Herald of Freedom.

"I entered upon the editorship of this journal," says Mr. Barnum, "with all the vigor and vehemence of youth. The boldness with which the paper was conducted soon excited widespread attention and commanded a circulation which extended beyond the immediate locality into nearly every State in the Union. But lacking that experience which induces caution, and without the dread of consequences, I frequently laid myself open to the charge of libel, and three times in three years I was prosecuted. A Danbury butcher, a zealous politician, brought a civil suit against me for accusing him of being a spy in a Democratic caucus. On the first trial the jury did not agree, but after a second trial I was fined several hundred dollars. Another libel suit against me was withdrawn. The third was sufficiently important to warrant the following detail:

"A criminal prosecution was brought against me for stating in my paper that a man in Bethel, prominent in church, had ’been guilty of taking USURY of an orphan boy,’ and for severely commenting on the fact in my editorial columns. When the case came to trial the truth of my statement was substantially proved by several witnesses and even by the prosecuting party. But ’the greater the truth, the greater the libel,’ and then I had used the term ’usury,’ instead of extortion, or note-shaving, or some other expression which might have softened the verdict. The result was that I was sentenced to pay a fine of one hundred dollars and to be imprisoned in the common jail for sixty days.

"The most comfortable provision was made for me in Danbury jail. My room was papered and carpeted; I lived well; I was overwhelmed with the constant visits of my friends; I edited my paper as usual and received large accessions to my subscription list; and at the end of my sixty days’ term the event was celebrated by a large concourse of people from the surrounding country. The court room in which I was convicted was the scene of the celebration. An ode, written for the occasion, was sung; an eloquent oration on the freedom of the press was delivered; and several hundred gentlemen afterwards partook of a sumptuous dinner followed by appropriate toasts and speeches. Then came the triumphant part of the ceremonial, which was reported in my paper of December 12, 1832, as follows:

" ’P. T. Barnum and the band of music took their seats in a coach drawn by six horses, which had been prepared for the occasion. The coach was preceded by forty horsemen, and a marshal, bearing the national standard. Immediately in the rear of the coach was the carriage of the orator and the President of the day, followed by the committee of arrangements and sixty carriages of citizens, which joined in escorting the editor to his home in Bethel.

" ’When the procession commenced its march amidst the roar of cannon, three cheers were given by several hundred citizens who did not join in the procession. The band of music continued to play a variety of national airs until their arrival in Bethel (a distance of three miles), when they struck up the beautiful and appropriate tune of "Home, Sweet Home!" After giving three hearty cheers, the procession returned to Danbury. The utmost harmony and unanimity of feeling prevailed throughout the day, and we are happy to add that no accident occured to mar the festivities of the occasion.’ "

The editorial career continued as it had begun. In 1830 The Herald of Freedom was sold to Mr. George Taylor.

The mercantile business was also sold to Horace Fairchild, who had been associated with it as partner since 1831, and a Mr. Toucey, who formed a partnership under the name of Fairchild & Co. Barnum had lost considerable money in this store; he was too speculative for ordinary trade, too ready, also to give credit, and his ledger was full of unpaid accounts when he finally gave up business.

In 1835 he removed his family to New York, taking a house in Hudson street. For a time he tried to get a position in a mercantile house, not on a fixed salary, but so as to derive a commission on his sales, trusting to his ability to make more money in this way than an ordinary clerk could be expected to receive. Failing in this he acted as a "drummer" for several stores until spring, when he was fortunate enough to receive several hundred dollars from his agent at Bethel. In May he opened a private boarding-house at 52 Frankfort street, which was well patronized by his Connecticut acquaintances as often as they visited the metropolis. This business not occupying his entire time, he bought an interest in a grocery store at 156 South street.

Although the years of manhood brought cares, anxieties, and struggles for a livelihood, they did not change Barnum’s nature, and the jocose element was still an essential ingredient of his being. He loved fun, practical fun, for itself and for the enjoyment which it brought. During the year he occasionally visited Bridgeport, where he almost always found at the hotel a noted joker, named Darrow, who spared neither friend nor foe in his tricks. He was the life of the bar-room, and would always try to entrap some stranger in a bet and so win a treat for the company. He made several ineffectual attempts upon Barnum, and at last, one evening, Darrow, who stuttered, made a final trial, as follows:

"Come, Barnum, I’ll make you another proposition; I’ll bet you hadn’t got a whole shirt on your back." The catch consists in the fact that generally only one-half of that convenient garment is on the back; but Barnum had anticipated the proposition —in fact he had induced a friend, Mr. Hough, to put Darrow up to the trick—and had folded a shirt nicely upon his back, securing it there with his suspenders. The bar-room was crowded with customers who thought that if Barnum made the bet he would be nicely caught, and he made presence of playing off and at the same time stimulated Darrow to press the bet by saying:

"That is a foolish bet to make; I am sure my shirt is whole because it is nearly new; but I don’t like to bet on such a subject."

"A good reason why," said Darrow, in great glee; "it’s ragged. Come, I’ll bet you a treat for the whole company you hadn’t got a whole shirt on your b-b-b-back!"

"I’ll bet my shirt is cleaner than yours," Barnum replied.

"That’s nothing to do w-w-with the case; it’s ragged, and y-y-you know it."

"I know it is not," Barnum replied, with pretended anger, which caused the crowd to laugh heartily.

"You poor ragged f-f-fellow, come down here from D-D-Danbury, I’m sorry for you," said Darrow tantalizingly.

"You would not pay if you lost," Barnum remarked.

"Here’s f-f-five dollars I’ll put in Captain Hinman’s (the landlord’s) hands. Now b-b-bet if you dare, you ragged c-c-creature, you."

Barnum put five dollars in Captain Hinman’s hands, and told him to treat the company from it if he lost the bet.

"Remember," said Darrow, "I b-b-bet you hadn’t got a whole shirt on your bob-back!"

"All right," said Barnum, taking off his coat and commencing to unbutton his vest. The whole company, feeling sure that he was caught, began to laugh heartily. Old Darrow fairly danced with delight, and as Barnum laid his coat on a chair he came running up in front of him, and slapping his hands together, exclaimed:

"You needn’t t-t-take off any more c-c-clothes, for if it ain’t all on your b-b-back, you’ve lost it."

"If it is, I suppose you have!" Barnum replied, pulling the whole shirt from off his back!

Such a shriek of laughter as burst forth from the crowd was scarcely ever heard, and certainly such a blank countenance as old Darrow exhibited it would be hard to conceive. Seeing that he was most incontinently "done for," and perceiving that his neighbor Hough had helped to do it, he ran up to him in great anger, and shaking his fist in his face, exclaimed:

"H-H-Hough, you infernal r-r-rascal, to go against your own neighbor in favor of a D-D-Danbury man. I’ll pay you for that some time, you see if I d-d-don’t."

All hands went up to the bar and drank with a hearty good will, for it was seldom that Darrow got taken in, and he was such an inveterate joker they liked to see him paid in his own coin. Never till the day of his death did he hear the last of the "whole shirt."


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Chicago: Joel Benton, "Chapter IV. Trying Many Ventures.," The Life of Phineas T. Barnum in The Life of Phineas T. Barnum (New York: The Century Co., 1918), Original Sources, accessed March 30, 2023,

MLA: Benton, Joel. "Chapter IV. Trying Many Ventures." The Life of Phineas T. Barnum, in The Life of Phineas T. Barnum, New York, The Century Co., 1918, Original Sources. 30 Mar. 2023.

Harvard: Benton, J, 'Chapter IV. Trying Many Ventures.' in The Life of Phineas T. Barnum. cited in 1918, The Life of Phineas T. Barnum, The Century Co., New York. Original Sources, retrieved 30 March 2023, from