Dicky Jessup: White Man in a Black Man’s World

Illustration of Richard P. “Dicky” Jessup, 1892 (San Francisco Examiner)

Growing up in Tomales, Henry Kowalsky dreamed of a life grander than working in his father’s general store. For years, he burned the midnight oil studying the law, until finally, in 1883 at the age of 24, he passed the California bar. With the help of his father, he opened a legal office in San Francisco, furnishing it in Victorian gilt and plush more suggestive of a parlor than a place of business.[1]

Kowalsky’s flamboyant performances—pulling out a pistol to defend himself from opposing counsel, falling asleep during trial—made good tabloid fodder, as did his life outside the courtroom, where he cast himself as a bon vivant, raconteur, and connoisseur of the arts, nonchalantly racking up debts residing at the luxurious Baldwin Hotel on Market Street.[2]

Baldwin Hotel, Market and Powell streets, 1885 (photo Marilyn Blaisdell Collection)

In 1887, he was appointed advocate-general of the California National Guard with the honorary title of colonel. That same year, the Colonel—as he insisted on being called—took on the case of an illegitimate son of a wealthy bachelor challenging his father’s will. As probate cases go, it was fairly commonplace, except for one twist: the father, Gershom Jessup, had his white son raised by a Black family in Petaluma.[3]

The case became one of the most sensationalistic of San Francisco’s Gilded Age, casting a spotlight on an issue bedeviling the country since Reconstruction: race.

Colonel Henry Kowalsky, 1889 (illustration public domain)

Jessup was manager of a stage line company in Marysville in 1865 when he became romantically involved with an attractive 18-year-old named Josie Landis. She became pregnant with his child. That same year, Jessup inherited a small fortune from his deceased brother Richard, co-founder of the prosperous California Steam Navigation Company.[4]

Moving to San Francisco, Jessup arranged for Josie to spend the final stage of her pregnancy at the North Beach home of Mrs. Abigail Nugent. A Black widow from Philadelphia, Nugent served as a midwife and nurse to the city’s elite. Two months after giving birth to a boy, Josie returned to Marysville. Keeping her child a secret, she quickly married a local dentist.[5]

Jessup named the boy Richard, or “Dicky,” after his recently deceased brother. He paid Nugent to raise him, and to have him baptized by the bishop of San Francisco’s Bethel African Methodist Church, T.M.D. Ward, where Nugent was a prominent member.[6] It was at the church that Nugent’s 18-year-old daughter Maggie met 42-year-old George Miller, a recently widowed barber from Petaluma.

Born and educated a free man in New Jersey, Miller came to San Francisco in 1850 to open a barbershop. In 1855, he moved his business and young family to Petaluma. He continued to spend a good deal of time in San Francisco, where he was actively engaged with the A.M.E. Church, the Black Freemasons, and the California Colored Convention, a group of businessmen, clergy, and journalists working to rescind the state’s racial restriction laws.[7]

Illustration of a Colored Convention held in 1876 (Frank Leslie’s Illustrated Newspaper)

Miller’s exclusive white clientele provided him with economic and social advantages that he put to use in Petaluma opening a state-supported “colored school” and the North Bay’s first A.M.E. Church. In 1868, two years after his wife’s death, Miller married Maggie Nugent, bringing her to town to live with him and his four children. Within a year, the couple had a child of their own.[8]  

Margaret Nugent Miller, 1886 (photo courtesy Sharon McGriff-Payne)

Soon afterward, Maggie’s mother brought Dicky, a sickly child, to reside with the Millers. She hoped the move would improve his health. Jessup continued to provide financially support the boy, occasionally visiting him at the Miller home, as did Dicky’s mother on one occasion. When Dicky came of school age, the Millers enrolled him with their own children in Petaluma’s “colored school” under the name Richard Miller.[9]

1870 Brooklyn Colored School in Oakland, Mary J. Sanderson, teacher (photo public domain)

At the time, George Miller and the Colored Convention were engaged in a case before the state Supreme Court to desegregate California schools. Although the court ultimately upheld the state’s “separate but equal” education law, a major economic recession led most California cities with “colored schools” to desegregate by 1875 as a cost-saving measure.[10]

Petaluma was the exception, maintaining its “colored school” until the state abolished them in 1880. As Dicky’s presence at the school violated Petaluma’s segregation adherence, he was forced to transfer to a white elementary school, where students bullied him so badly the Millers withdrew him for homeschooling.[11]

Washington College, Alameda County, 1878 (illustration David Rumsey’s Historical Map Collection)

In 1876, Jessup instructed Maggie—George Miller having unexpectedly died in 1873—to board 10-year-old Dicky in Washington College, a technical school in Alameda County under the name Richard Miller. He was afraid Josie’s family, having recently learned of the boy’s existence, would try to steal him away. Dicky lived with Maggie during school breaks.[12]

That same year, Maggie’s mother died, leaving her a sizable inheritance.[13] Her four stepchildren grown and gone, Maggie decided to move with her seven-year-old son Hoddie to Napa, where she eventually purchased a ranch, opened a restaurant, and married a Black barber named Ed Hatton.[14]

Ad for Maggie’s Arcade Restaurant (Napa Register, 1887).

In 1881, Dicky’s mother Josie died. Jessup had Maggie pull Dicky out of the Alameda technical school and send him to work on a friend’s ranch in San Diego, ending financial support for the boy. Within a year, Dicky returned to live with Maggie in Napa, working in a tannery and as a bootblack in her husband’s barbershop.[15]

Jessup died in 1886 at Harbin Springs in Lake County while seeking treatment for his rheumatism. In his will he named his brother and two sisters as sole beneficiaries of his estate. The estate was valued at $140,000, or $5 million in today’s currency.[16]

Maggie engaged Jerry Mahoney, a private detective, to determine if 20-year-old Dicky had a claim to the estate. Mahoney enlisted Colonel Kowalsky as legal counsel. Borrowing $20,000 ($600,000 in today’s currency) against a prospective settlement, Kowalsky filed a probate challenge and sent Mahoney scouring the state for witnesses to testify to Jessup’s fatherly relationship with Dicky.[17]

Senator Jeremiah H. Mahoney, 1896 (illustration public domain)

A media circus erupted around the trial, putting Dicky in the public spotlight. Mahoney took the young man under his wing, introducing him to the life of white luxury denied him by his father. To pay for his posh hotel, fancy meals, and tailored suits, Dicky borrowed against his prospective settlement at usury rates.[18]

In district court, Kowalsky was able to convince the judge that Jessup, through his actions and public acknowledgements, had legitimized Dicky as his offspring, entitling him to the entire estate. Jessup’s siblings filed an appeal with the state’s Supreme Court, who affirmed the lower court ruling. [19]  

Undeterred, the siblings filed a second appeal. A new presiding judge, Charles Fox, reversed the ruling. Although he cited insubstantial evidence, the main thrust of his decision was race.[20]  

California Supreme Court Justice Charles Fox (photo public domain)

Fox believed Jessup’s actions toward Dicky were not those of a loving father, but a punitive one. Why else would he have the boy brought up by a Black family, “considered inferior and by most white people as degrading,” having him take the family’s surname, attend a “colored school,” and work in a Black barber shop? Fox also speculated that Jessup’s cut off of funding for Dicky the same year the boy’s mother died, indicated he had agreed to provide support only during her lifetime, most likely out of fear she would expose their affair if he didn’t.[21]

Following the decision, Kowalsky incited a campaign among Black political leaders to oppose Fox’s reelection to the bench. It quickly escalated into death threats against the judge.[22] After Kowalsky filed for a new trial in district court, he discovered his key witness, Maggie Nugent Miller Hatton, refused to testify.

Maggie’s relationship with Dicky had apparently deteriorated during his time under Mahoney’s tutelage. To convince her to retestify, Kowalsky secured a $5,000 promissory note for her against the prospective settlement.[23]

The retrial once again ended in Kowalsky’s favor. Jessup’s siblings filed another appeal, but this time the two sides negotiated a settlement, granting one-third of the estate to the siblings. Dicky walked away with $90,000, or $3 million in today’s currency.[24]

Colonel Henry Kowalsky, 1899 (photo public domain)

Of that amount, Kowalsky took $40,000 for his fee. Another $20,000 went to paying off the loan he secured at the beginning of the trial. Mahoney, Kowalsky’s legal associate, and the court-appointed administrator of Jessup’s estate got $15,000. Dicky’s loan sharks got $10,000. That left Dicky with $5,000, which he legally owed to Maggie. She never received a penny.[25]

After the trial, Dicky moved to Sacramento to live with Mahoney, who had used his newfound fame to get elected to the state senate. Mahoney got him a job working as a senate page for $3 a day. After the senator’s death in 1897, Dicky vanished from sight.[26]

Maggie and her family moved to Oakland. She died there in 1928. Kowalsky went on to land a number of high-profile cases, including defending Belgium’s King Leopold II against charges of genocide in the Congo. He died in 1914, still living the high life at San Francisco’s Palace Hotel.[27]

******

A version of this story appeared in the Petaluma Argus-Courier, February 2, 2024


FOOTNOTES:

[1] “Col. Kowalsky was Reared at Tomales,” Petaluma Courier, December 9, 1914; “Aneurysm Cause of Kowalsky’s Sleeping Sickness,” Sacramento Bee, November 30, 1914.

[2] “Henry Kowalsky Called by Death,” San Francisco Chronicle, November 29, 1914.

[3] “Colonel Kowalsky is Dead,” San Francisco Bulletin, November 28, 1914.

[4] “Estate of Gershom P. Jessup, Deceased,” Decided March 29, 1891, by California Superior Court, Reports of Decisions in Probate, Volume 2 (San Francisco Probate Department, James Vincent Coffey, Bancroft-Whitney, 1909), pp. 480-481; “First Boatbuilder on the Pacific Coast,” San Francisco Call and Port, March 9, 1902.

[5] Reports of Decisions in Probate, Volume 2, p. 481. “The Lost Heir,” San Francisco Examiner, September 8, 1887.

[6] Reports of Decisions in Probate, Volume 2, pp. 482-483; “Young Jessup Wins,” Napa Register Weekly, July 5, 1889; “Jessup Contest,” Napa Register Weekly, September 19, 1890.

[7] John Sheehy, “Black Sonoma County’s Birth,” PetalumaHistorian.com, https://petalumahistorian.com/black-sonoma-countys-political-birth/

[8] Sheehy, https://petalumahistorian.com/black-sonoma-countys-political-birth/

[9] Reports of Decisions in Probate, Volume 2, p. 482; “Jessup Contest,” Napa Register Weekly, September 19, 1890.

[10] Delilah Leontium Beasley, The Negro Trail Blazers of California (Los Angeles: Times Mirror Printing,1919) p. 180-182; Jo Ann Williamson, Lori Rhodes, Michael Dunson, “Chapter 7 A Selected History of Social Justice in Education,” Review of Research in Education, November 15, 2016, Vol. 31 (1), pp. 195–224; “1874 Ward V. Flood,” Blackpast.org, https://www.blackpast.org/african-american-history/ward-v-flood-1874/.

[11] Charles Wollenberg, All Deliberate Speed: Segregation and Exclusion in California Schools, 1855-1975. (Berkeley, CA: University of California Press, 1976), 25; “Local Dots,” Petaluma Courier, July 21, 1880; “Jessup Contest,” Napa Register Weekly, September 19, 1890.

[12] Reports of Decisions in Probate, Volume 2, p. 484.

[13] “Died, The Elevator, October 25, 1873; Maggie inherited property valued at $8,000: “The Jessup Case,” Napa Register Weekly, September 19, 1890.

[14] “Dancing Party,” Napa Register Weekly, November 30, 1883; “Real Estate Transfers,” Napa Register Weekly, March 5, 1885; “Local Brevities,” Napa Register Weekly, April 1, 1886; “Local Brevities,” Napa Register Weekly, August 5, 1887; “Local Briefs,” Napa Valley Register, January 17, 1890; “Death of Edward Hatton,” Napa Register Weekly, May 11, 1897.

[15] Reports of Decisions in Probate, Volume 2, p. 485; “Gershom P. Jessup’s Estate,” Lawyers’ Reports Annotated, Book VI (The Lawyers’ Co-operative Publishing Company, 1890), p. 600.

[16] Reports of Decisions in Probate, Volume 2, p. 477; “Stripped of His Birthright,” San Francisco Examiner, April 9, 1893: The Jessup estate, initially valued at $93,000 at the time of Jessup’s death, rose in value to $140,000 by the time of the settlement in 1892.

[17] “Mahoney Did It,” San Francisco Call and Post, October 13, 1894.

[18] “Young Jessup’s Estate,” San Francisco Examiner, July 2, 1892; “Stripped of His Birthright,” San Francisco Examiner, April 9, 1893; “Mahoney Did It,” San Francisco Call and Post, October 13, 1894.

[19] Reports of Decisions in Probate, Volume 2, p. 476.

[20] Lawyers’ Reports Annotated, Book VI, pp. 594-601.

[21] Lawyers’ Reports Annotated, Book VI, pp. 600-601.

[22] “Offices Seeking Men,” San Francisco Examiner, August 6, 1890; Stockton Evening Mail, August 7, 1890; “The Fox Resolutions,” San Francisco Call and Post, August 7, 1890.

[23] “To Protect Her Claim,” San Francisco Examiner, September 8, 1894; Hatton’s promissory note was issued September 12, 1890, she testified September 19th.

[24] “Stripped of His Birthright,” San Francisco Examiner, April 9, 1893.

[25] In the Hotel Corridors,” Sacramento Bee, December 8, 1892; “Stripped of His Birthright,” San Francisco Examiner, April 9, 1893; “Made Certain of His Fees, San Francisco Examiner, May 15, 1893; “Young Jessup’s Note,” San Francisco Call and Post, September 8, 1894; “To Protect Her Claim,” San Francisco Examiner, September 8, 1894.

[26] “Stripped of His Birthright,” San Francisco Examiner, April 9, 1893; “Jessup is Penniless,” Pacific Bee, December 27, 1893; “State Senator Mahoney Dead,” Sacramento Bee, December 24, 1897; “List of Letters,” Sacramento Union, October 11, 1897: Jessup still in Sacramento.

[27] “Deaths,” San Francisco Examiner, December 28, 1928; “Aneurysm Cause of Kowalsky’s Sleeping Sickness,” Sacramento Bee, November 30, 1914.

Author: John Patrick Sheehy

John is a history detective who digs beneath the legends, folklore, and myths to learn what’s either been hidden from the common narrative or else lost to time, in hopes of enlarging the collective understanding of our culture and communities.