“There … (are) gentlemen enough in Canterbury whose bond for that amount would be as good or better than mine, and I should leave it for them to do Miss Crandall that favor,” May told the messenger.68 “But, are you not her friend?” the messenger asked. “Certainly,” May replied. He said Miss Crandall did not need his help, and her accusers would be embarrassed by her unjust arrest.69
“But, sir, do you mean to allow her to be put into jail?” the man asked. “Most certainly,” May replied, “if her persecutors are unwise enough to let such an outrage be committed.” May wrote that the man “hurried back to tell Mr. Judson.”70
Crandall’s supporters had already investigated the arrangements for her stay at the Brooklyn jail. In response to a question from Samuel May, prison officials said that Crandall likely would stay in an unoccupied room that two years earlier held a notorious murderer, Oliver Watkins. Watkins had strangled his wife with a whipcord. He was convicted and sentenced to death by hanging. Local tavern owners had anticipated a huge crowd and brisk business on the day of Watkins’s execution. They had ordered additional rum and spirits and hired an extra guard at the prison to monitor Watkins so he would not commit suicide.71 The tavern owners persuaded the authorities to move Watkins to the debtor’s room, where he was more easily monitored.
On the day of the hanging, August 2, 1831, wagons and carriages jammed all of the roads leading into Brooklyn, and an immense crowd gathered. Men filled the taverns. Historian Ellen Larned wrote that the execution was carried out “in stillness that seemed of the dead rather than that of the living.”72 The silence, however, quickly disappeared. “The vast throng present, the abundant supply of liquor and scarcity of food made the afternoon and following night a scene of confusion and disorder.”73
The officials at the Brooklyn jail said that Prudence Crandall would stay in the debtor’s room previously occupied by Oliver Watkins. May considered this good news. The notoriety of the Watkins execution was fresh in the minds of Windham County residents; May believed jailing Prudence Crandall in the same prison room where Watkins stayed “would add not a little to the public detestation of the Black Law.”74
May gathered fresh linens from the Benson family, who lived a short distance away, and remade the bed at the jail. He brought an additional bed into the debtor’s room so that Anna Benson—who did not want Crandall to spend the night in jail alone—could stay in the room with Crandall.75 At two o’clock in the afternoon, another messenger told May that if he did not post Crandall’s bail immediately, a sheriff would transport Crandall from Chauncey Bacon’s house in Canterbury to the jail in Brooklyn. The opponents of the school suddenly realized that locking Prudence Crandall in the Brooklyn jail might result in sensational news stories casting Canterbury and the Black Law in an unfavorable light. May refused to pay Crandall’s bail. Instead, he traveled with George Benson to the jail. When Crandall’s carriage pulled up to the prison entrance, May and Benson greeted her. May spoke with her before the sheriff led her inside.76
“If now you hesitate, if you dread the gloomy place so much as to wish to be saved from it, I will give bonds for you even now,” May told Crandall.77 “Oh no,” she replied. “I am only afraid they will not put me into jail … I am the more anxious that they should be exposed, if not caught in their own wicked devices.”78
Sheriff Roger Coit slowly led Crandall down the walkway to the entrance of the jail. “He was ashamed to do it,” May wrote.79 Before Coit took Crandall through the door, he looked to see if someone might rush forward with the bail for Crandall’s release. Coit whispered to two men standing nearby. The men walked over to May and made one last plea for Crandall’s bail. “It would be a shame, an eternal disgrace to the state, to have her put into jail, into the very room that Watkins had last occupied,” they told May.80 “Certainly, gentlemen,” May replied, “and you may prevent this.”81
“We are not her friends …” the men said, “we don’t want any more niggers coming among us. It is your place to stand by Miss Crandall and help her now. You and your abolition brethren have encouraged her to bring this nuisance into Canterbury, and it is mean (for) you to desert her now.”82
May told the men he had not deserted Crandall. He candidly told them that Crandall’s arrest and prosecution would help expose the infamous Black Law. May said the people of Connecticut would not “realize how bad, how wicked, how cruel a law it is, unless we suffer her persecutors to inflict upon her all the penalties it prescribes. … It is easy to foresee that Miss Crandall will be glorified, as much as her persecutors and our State will be disgraced, by the transactions of this day and this hour.”83
The men cursed May, and Sheriff Coit led Crandall into the debtor’s room where Oliver Watkins had spent his last night. As May and Benson walked from the jail to May’s carriage to return home to Brooklyn, May noticed the sunset. “The sun had descended nearly to the horizon; the shadows of night were beginning to fall around us. … So soon as I had heard the bolts of her prison-door turned in the lock, and saw the key taken out, I bowed and said, ‘The deed is done, completely done. It cannot be recalled. It has passed into the history of our nation and our age.’”84
After the tumult of the day, the night passed quietly. On Friday, George Benson posted the bond for Prudence, and she was set free on bail awaiting trial. As May had predicted, word of her imprisonment spread quickly. Newspapers throughout the country printed stories about the female schoolteacher who had spent a night in jail for the crime of teaching black women, including the Liberator, where guest editors Oliver Johnson and George Bourne continued to write and publish in William Lloyd Garrison’s absence.
“Savage Barbarity! Miss Crandall Imprisoned!!! The persecutors of Miss Crandall have placed an indelible seal upon their infamy!” the Liberator screamed. “They have cast her into prison! Yes, into the very cell occupied by Watkins the Murderer!!”85
In response to the sensational news accounts, Andrew Judson received threatening letters from readers throughout the Northeast and as far away as Pennsylvania.86 One person had a unique proposal. The man offered to “jail” Judson in a portable cage and display him for the curious of England and France. The man promised “good food and no whipping or compulsion unless absolutely necessary.”87
Crandall’s opponents tried to counter the bad press with their own letters. They questioned the assertion that Crandall had spent the night in the same prison cell used by a murderer. “Some person has put in wide circulation the story that she was confined in the cell of Watkins the murderer,” Andrew Judson and Rufus Adams wrote in a joint letter. “This is part of the same contrivance to ‘get up more excitement.’ She never was confined in the murderer’s cell. She was lodged in the debtor’s room, where every accommodation was provided, both for her and her friends, whose visits were constant.”88
The complaining by Judson and Adams did little to counteract the story of Prudence Crandall’s night in jail. Their criticism focused on the word “cell.” They said Prudence did not spend the night in the “cell” where Watkins spent most of his days in jail. Their complaints were trivial and misleading by their own admission; they acknowledged that the debtor’s room where Crandall stayed was the same room where Watkins had spent “the last days of his life … to receive the clergy and his friends.”89
Days after Crandall’s imprisonment, Samuel May received a letter from Arthur Tappan. Tappan may have read one of the many press accounts of Prudence Crandall’s arrest and learned of May’s defending Crandall and her school. While they had not kept in touch, Tappan and May knew each other from years before. Tappan’s father worked as a silversmith in Northampton, Massachusetts, and later went into the dry goods business. In the spring of 1801, when Arthur was fourteen,