Archives of Maryland
(Biographical Series)

Josiah "Joe" Bailey (b. 1828 - d. ?)
MSA SC 5496-1535
Fled from slavery, Talbot County, Maryland, 1856


    Josiah "Joe" Bailey was led out of slavery, along with his brother and two others, by Harriet Tubman in November of 1856. His owner, William R. Hughlett, was a farmer and ship timber dealer. Owning forty slaves, he was also one of the largest slaveholders on Maryland's Eastern Shore. At the time of flight, Joe was a new acquisition for the wealthy businessman. His old owner had hired him out to Hughlett for the preceeding six years, during which time Bailey supervised the overall operations of Hughlett's land, saving him the expense of hiring an overseer. For a period, Joe's former owner refused to sell him, but Hughlett, eventually purchased the slave for a one thousand dollar down payment, and one thousand dollars to be paid at a later date.1 This was an unusually high value, and is reflective of Bailey's skill and experience in his new owner's chosen industries.

    Soon after the purchase, Hughlett rode down to the slave quarters and called for Joe to come out. He was then inexplicably told to "strip and take a whipping." Joe hesitated before submitting, asking if he had ever been unfaithful in the past. Bailey felt that all his work the past six years did not warrant such cruel treatment. He would later say that Hughlett admitted he had no complaints of Joe, but told him:

    "the first lesson my niggers have to learn is that I am master, and that they are not to resist or refuse to obey anything I tell 'em to do. So the first thing they've go to do, is to be whipped; if they resist, they got it all the harder; and so i'll go on, till I kill       'em, but they've got to give up at last, and learn that I'm master."2
    Joe took his punishment without saying one word, and pulled his shirt over his bleeding back. Conflicting souces attribute the abuse either to Bailey's altercation with a fellow slave or to Hughlett's desire to establish dominance over even his most valuable slaves. Regardless, Hughlett successfully produced in Joe's mind an unwavering determination to leave slavery or die, which probably would not have occurred without the abuse. As with many blacks in the area, Bailey was familiar with the increasing anti-slavery activity of Harriet Tubman and her various accomplices. In fact, his friend Samuel Green Jr. had successfully made off to Canada with her guidance just two years earlier. In writing to his father the Reverend Samuel Green implored him to "tell P. Jackson to come on Joseph Baley com on, kom more."3 Being personally acquainted with Tubman and her family, Joe decided to use his contacts to escape slavery. He took a boat across the Choptank to the dwelling of Harriet's father, Ben Ross, at Poplar Neck, Caroline County.  The scars on his back still not yet healed, Joe said to Ben, "Next time Moses comes, let me know."4  A similar situation took place with Joe's brother, William "Bill" Bailey, who was owned by John C. Henry, another prominent Eastern Shore slaveholder. Bill had been recently whipped while he was hired out to Hughlett, and the brutality of this act motivated him to run away. Though this decisive whipping was not at the hands of his owner, Bill considered Henry more in fault than the man to whom he was hired.

    Within three weeks, on November 15, 1856, Joe Bailey and his brother Bill joined Harriet Tubman. They traveled with fellow slaves Peter Pennington, age twenty-five, and Eliza Manokey, all set to head north and free themselves from bondage. At age thirty-six, Harriet Tubman's was on her seventh or eighth journey leading slaves to freedom. From the start of their journey, slave catchers were in close pursuit of the group, and the runaways "hid in potato holes by day, while their pursuers passed within a few feet of them."5 However, the group was forced to separate, disparate members traveling by wagon, by boat or on foot as they approached free soil. Further adding to the difficulties, at one point in their journey, Harriet's head began to ache ferociously. She collapsed in plain view, falling into one of her recurring, involuntary "sleeps."  Joe had trouble convincing the others not to abandon her, but Tubman eventually arose and continued on. A runaway advertisement was placed in the Baltimore Sun on November 18, 1856, offering a one thousand five hundred dollar reward for Joe Bailey's capture and lodging in the jail at Easton, Talbot County, three hundred dollars for Bill, and eight hundred dollars for Peter.  The advertisement noted that Joe had "a remarkable scar on one of his cheeks, not positive on which it is, but think it is on the left, under the eye; has intelligent countenance, active and well made."6  The total reward of two thousand six hundred dollars, offered by the three Eastern Shore owners, caught the attention of the official patrols and slave hunters alike.

    They likely passed through the house of Samuel Green, whose son had encouraged Bailey's flight initially. He was also a local preacher in the Methodist Episcopal Church and a common supporter of Tubman's efforts. Green, who had been suspected of harboring runaways, was ultimately convicted of distributing the abolitionist novel Uncle Tom's Cabin in 1857. After traveling over a full day, the group arrived in Delaware. There, they saw many runaway advertisements posted up at all the railway depots and towns leading north. The ads, located all around the Eastern Shore of Maryland and Delaware, were routinely taken down, often by sympathetic whites and free blacks. By this point, the reward offered for Joe, who was considered the leader of the party, was set at an unprecedented $1500.

    The group ended up at the entrance of the Market Street Bridge, which crosses the Christiana River at Wilmington, Delaware.7 The bridge was always closely guarded by slave catchers because it was a strategic crossing point for slaves on their way to the north. When Joe’s group arrived in late November, the bridge was guarded by police officers. Harriet swiftly decided to separate the group in the houses of different friends until further notice. She then contacted famed abolitionist and Underground Railroad conductor, Thomas Garrett, who lived and owned a store a few blocks from the bridge. Garrett devised a plan to transport the fugitives, utilizing his various sympathetic contacts in the area. He enlisted a group of black bricklayers, as well as several whites who worked near the bridge . The next morning, the bricklayers' two wagons left Wilmington, their occupants singing and shouting loudly so as to deflect suspicion of their covert activity. The wagons returned after dark with the men singing and acting like they were drunk, even louder than when they had departed. On this return trip, however, they were carrying Bailey and his companions lying together beneath the straw. When they reached the checkpoint, the patrols did not bother to check the wagon. Once on Garrett's side of the bridge, the fugitives were given supplies to continue their trip North. Soon after they arrived in Philadelphia, meeting with prominent abolitionist William Still. He would make an entry in his account book of the aid that he supplied the slaves: Josiah and Wm. Bailey cash $3.25, Harriet Tubman $2.50.8 It was also here that Joe was interviewed, revealing the details of his life in slavery and motivations for fleeing.

    The group was forwarded to New York, and where they received assistance from the local Anti-Slavery office.  Mr. Oliver Johnson said to Joe, "Well, I am glad to see the man who is worth $2,000 to his master."9  Bailey became very gravely concerned that the advertisement had made him so easily recognizable, likely due to the large scar on his face. Joe asked how far away Canada was by train, and when shown the 300 mile route to Niagara, he was even further discouraged from using such a public form of transport. Harriet gave him some encouragement, telling him that the Lord "had been with them in six troubles, and he would not desert them in de seventh."10

    Continuing from New York City, the group passed through Albany and Syracuse with additional help from agents there. Joe had been silent for much of the trip, though his fellow fugitives sang songs and conversed quite a bit. Tubman would later say that, "He sat wid his head on his hand, an' nobody could 'rouse him, nor make him take any intrust in anything."11 After a long journey, they reached the Niagara suspension bridge that seperated New York and Canada.  While the other fugitives were overjoyed, and sang in celebration, Joe remained in his slump, still wary of possible capture. As they were making their way over the bridge, Harriet went to him and exclaimed, "Joe!  You've shook de lion's paw!  Joe, you're in Queen Victoria's dominions!  You're a free man!"  Bailey finally emerged from his dejection, began crying, and loudly singing, "Glory to God and Jesus too, One more soul got safe; Oh, go and carry the news, one more soul got safe!"12  Joe's feet were the first to touch down in Canada after the train conductor's. A lady gave the sobbing man her handkerchief, as he exclaimed, "Tank de Lord!  Dere's only one more journey for me now, and dat's to Hebben!"13

    It was no surprise that they reached freedom, as none of the many slaves that Harriet Tubman helped over the years were ever recaptured. Joe Bailey and his brother settled in the St. Catharine's area of Ontario, where many former Eastern Shore fugitives had established themselves. It was here that the Baileys were recruited by Tubman to assist John Brown in his ambitious strike against slavery in Virginia. Along with Eastern Shore natives Thomas Elliot, Denard Hughes, and Peter Pennington, among others, Tubman had initially organized a legitimate force to support Brown.14 The Canadian contingent ultimately decided not to join him in the ill-fated 1859 mission. However, even their consideration of Brown's plan was evidence of just how fervently Joe Bailey and his fellow fugitives opposed the institution. Though little else is known about his life in Canada, the extravagant reward offered for his return made Joe's story legendary among abolitionists and slaveowners alike.

Footnotes  -

1Kate Clifford Larson. Bound for the Promised Land: Harriet Tubman, Portrait of an American Hero. Ballantine Books: New York, NY, 2004, p. 134. 
William Still. The Underground Railroad:  A Record of Facts, Authentic Narratives, Letters, etc.  (Philadelphia: Porter & Coates, 1872), pp. 272-274

2 University of North Carolina at Chapel Hill Libaries: Documenting the American South.  "Harriet, the Moses of Her People, Bradford, Sarah H.", 40.

3Richard A. Blondo. Samuel Green: A Black Life in Antebellum Maryland. Unpublished M.A. Thesis. University of Maryland, 1988. p. 21.

4 UNC ,"Harriet", p. 41.

5Ibid, 42.

6"Two Thousand Six Hundred Dollars Reward" Baltimore Sun, 22 November 1856.

7 Judith Bentley, Dear Friend: Thomas Garrett and William Still, Collaborators on the Underground Railroad. (New York: Cobblehill Books, 1997), 36.

8 Ibid, 43.

UNC ,"Harriet", p. 46.

10 Ibid, 47.

11 Ibid, 48.

12 Ibid, 52.

13 Ibid, 53.

14 Larson, p. 159.

Researched and Written by David Armenti, 2012.

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