O'Brien was/is a VERY common Irish name. I do not know if there was connections between all of the following O'Briens. However, Ann O'Brien Costello, John O'Brien and Patrick O'Brien were siblings.

Parent of Ann (DOB c. 1827), John DOB c 1837) and Patrick (DOB ??)

Birth of father:

Birth of mother: Mary born circa Ireland circa 1788

Died after 1860

1860: 1st district Ward 12, Ann Costello, age 31 "lady" $6,000, James Costello 4, John O'Brien age 25, liquor dealer, $2,000, adults all born Ireland, James born New York, Mary O'Brien age 72.

Children:

1. Ann O'Brien Costello (wife of James, mother of James Patrick) (c 1827-1889) born Ireland died Brooklyn

   Birth: Ann Costello, nee O'Brien, circa 1827 Ireland

   Marriage to James Costello: circa 1856

   Child: James circa 1857. Married Julia. L _____. No children. Died c 1884.

   Death of James Costello, husband of Ann, mother of James: December 1856

   Ann Costello's husband died in 1856±. Her only child, James, born in 1856 died in 1884±

   1887: "James' Costello's" saloon was the scene of a stabbing.

   1865:

   1870 Census: Ward 12, Anna Costello 30, keeping house, $17,000, born Ireland, James Costello 13, at school, Ellen O'Brien 14, at school, both children born New York.

   1875 Census: Living in the same house as James Donovan, Alderman, maybe Van Brunt, brick, $8,000, Anne Costello, Annie M age "38", born Ireland, James son age 19, Ellen O'Brien "a daugh" age 17.

   1885, June: In December 1856 James Costello Sr. owner in fee of land and buildings on Van Brunt and Sullivan streets valued in 1885 at $30,000 died living a widow, Ann, and a son James Patrick. He left a will which was probated. It gave the first half of his property to his wife provided she did not remarry. It gave the second half to his son James Patrick and his heirs and assigns unless his son died before his wife in which case everything would go to her. James Patrick died in November 1884 leaving a wife, Julia L. and he was survived by his mother, Ann. James Patrick left a will that stated that his mother and wife would take equally during their lives the share of James P's part of his father's estate. James P's wife, Julia, contested the will and sued Ann Costello. I could not find the results of the suit.

   I cannot find any of them in the censuses other than 1870. 1884 November Death of James Costello, son of Ann and James, based on anniversary mass in 1885. I cannot find the death of James Patrick Costello in Brooklyn in 1884. Was it earlier?

   November 1885, An anniversary mass for the soul of James Costello, son of Ann Costello, nee O'Brien, and the late James Costello, was celebrated at the Church of the Visitation, Red Hook.

   Ann Costello, wid, 1862, Sullivan n Van Brunt, Brooklyn, New York, Brooklyn, New York, City Directory, 1862. James no listed.

   Ann Costello, wid, 1873, 100 Sullivan, Brooklyn, New York, Brooklyn, New York, City Directory, 1873

   1876, Ann Costello, laundress 100 Sullivan

   1885, Costello, Ann 100 Sullivan

   1886

   Father William Sherman, a Catholic priest of Red Hook Point, "forgot" his vows of celibacy and married Tillie McCoy, of Douglass street. When he was ordained priest the first person he called on after visiting his parents was Mrs. Costello, a rich widow lady living at 100 Sullivan Street, Red Hook Point. It was said he went to college with Mrs. Costello's son. Father Sherman was assigned to the church of the Visitation in Red Hook. Mrs. Costello was described as being past 50 and suffering from "sick headaches". Mrs Costello was very upset by Father Sherman's indiscretions. She condemned the girl, who she felt had led the priest astray. She encouraged Father Sherman to put the girl away. Mrs Costello told an Eagle reporter that Father Sherman had come to her and told his story - that he had gone to New York with the McCoy girl. There he "was made drunk and drugged", and in that condition went through the mariage ceremony with a Protestant minister. He asked her for money to return to Philadelphia where he planned to enter a monastery to repent his sins. Tillie McCoy was reportedly back in Brooklyn.

   HOWEVER, "An Admirer of Justice" wrote to the Eagle contending that Mrs. Costello's comments were all false. The writer said he was a friend of the priest and his bride and they were happily living in Brooklyn as a married couple and Sherman had no intention of repudiating his marriage . The couple were said to have had a "hearty laugh" at Mrs. Costello's comments.

   Miss McCoy comes from a fine family and and Father Sherman and she were very fond of each other long before they were married."

   Father Sherman had "had all he wanted of the Catholic religion and will never re-enter the church."

   The Brooklyn Eagle cover the story of the marriage of William J. Sherman and Tillie McCoy in several articles. They claimed that Tillie and William had been friends since childhood. William had proposed to Tillie, but she had refused. William was the son of a wealthy builder, Michael Sherman. On the urging of his mother he entered the seminary to become a priest and after his ordination in Troy, N.Y. returned to Brooklyn and the church of the Visitation. He resumed his courtship of Tillie McCoy and the couple eloped. The families were extremely upset. An additional article says the couple was hooted out of Brooklyn.

   In 1884 a bartender for James Costello was listed at 252 Van Brunt when he was accused of selling liquor on Sunday.

   1887 April. "James Costello's" saloon at Van Brunt and Sullivan was the scene of a stabbing when one man stabbed another in the throat.

   In August 1888 Mrs. James Costello was in Patchogue with Miss Nellie O'Brien of Fort Greene Place and Mr. and Mrs. James M. Brady of St. Mark's ave.

   1890 Costello, Ann M wid, James, liquors 352 Van Brunt, home 100 Sullivan

   1889 May 16, Annie Costello, age "50" of 100 Sullivan died suddenly at her residence of heart disease.

   1889, May- died Ann Costello, age 62 years, 100 Sullivan Street, funeral Visitation, burial Calvary

   1889 Surrogate notice named: Michael O'Brien, John O'Brien, Ellen O'Brein, Thomas F. O'Brien, Mary Brady, Mary McNamara, and Agnes Buckley.

   Estate files: John O'Brien sole executer of the will of Anna Costello, died 166 May 1889 her will was signed by John Madigan. She left no husband, no children, no descendants of children, no father or mother. Her kin were Michael O'Brien of San Francisco California, the petitioner, John O'Brien, of Brooklyn her brother, Ellen O'Brien,* Thomas F O'Brien and Mary Brady of Brooklyn children of Patrick O'Brien her deceased brother. Mary McNamaran and Agnes Buckley of San Francisco the children of Bridget O'Niel her deceased sister. All of the said persons were over the age of 21. Dated May 22, 1889 Brooklyn John O'Brien. One Michael O'Brien of Boston Massachusetts appears to have stepped forth and made his claim.

   John Madigan swore that Ann Costello "made her mark". There is no indication of what the will actually said or what kind of assets Ann Costello had and got what, if anything.

   *This was her niece who she once listed as her daughter.

2. O'Brien, John, (c 1837- ) Ireland - Van Brunt near Sullivan

   352 Van Brunt North West corner of Van Brunt at Corner Sullivan, 1886 brick building.

   1870 BE liquor dealer list VAN BRUNT near Sullivan, O'Brien J.

   1862 O'Brien, John liquors Van Brunt and Sullivan

   Birth: Circa 1837 Ireland. He was a brother of Ann O'Brien Costello.

   Immigration:

   Marriage: Mary

   Children:

   1. Patrick 1864

   2. John 1866

   3. Michael 1868

   4. Annie 1873

   5. Joseph 1877

   6. Eddie 1880

   1863, O'Brien, John liquor 149 Van Brunt 1863 149 Van Brunt corner of Sullivan, 1865 Van Brunt corner Sullivan Note: I believe that the addresses changed and were renumbered circa 1872.

   Civil War Draft Registration 1863-1865: O'Brien, John, age 34 liquors, Van Brunt, 70th reg.

   1860 August: O'Brien's "rum mill" corner of Van Brunt and Sullivan was the meeting place before a boxing match between two local boys. The fight was not a grudge match but was set up for a prize. The police arrested the two "pugilists".

   1867 - Licence granted O'Brien, J, cor Van Brunt and Sullivan streets.

   1870 directory, O'Brien, John, liquors, Van Brunt c Sullivan.

   1870 Census: O'Brien, John 33, ret. liquor dealer, $10,000, Mary 28, Patrick 6, John 4, Michael 2, and domestic servant, Hickey, Michael 23, bartender

1870: William Fitzgerald had an altercation with Patrick Dooley outside O'Brien's saloon at the corner of Sullivan and Van Brunt. Fitzgerald's brother was responsible for the loss of Dooley's dog. Furthermore Fitzgerald's father had refused to drink with Dooley thereby insulting him. Dooley drew a pistel and shot Fitzgerald in the face. Fitzgerald lost the sight in his right eye.

1872, 1873, 1874, O'Brien, John liquors 352 Van Brunt.

1876 John O'Brien, liquors, 353 Van Brunt and 524 Court, home 435 Van Brunt

1877 John O'Brien, liquors, 354 Van Brunt.

1878, 1879, 1880, 1881, 1882, 1884, 1886, John O'Brien, liquors, 526 Court st, home Sullivan and Van Brunt and 352 Van Brunt, home 354 Van Brunt

1888, 1890, 1894 John O'Brien liquor 524 Court street, home 262 President

1880 Census: 354 Van Brunt, O'Brien, John, age 40 liquor dealer, born Ireland, Mary age 33, wife, Patrick 15, John 14, Michael 12, Annie 7, Joseph 3, Eddie 4 months, Finn?, Mary 70 mother in law. Note: Fred Greaf, liquor dealer, was at no 358 Van brunt in 1880 and Patrick Connor, grocer, was at 360 Van Brunt in 1880

In 1873 John O'Brien was the canvasser for the 3rd district 12th ward.

1885: October John O'Brien et al against William F Mooney et al in pursuance of a judgement to be sold at public auction (hard to read) a parcel of property with buildings at or near Carroll street and Van Brunt and more at Smith Street. Is this the same John O'Brien??

1886: November Service on John MaCartney - To be sold a public auction for non payment of public taxes due in the amount of $32.03 - lot number 2 on block 38 12th ward. Notice given by John O'Brien, No 354 Van Brunt Street.

1887: December, John O'Brien of 354 Van Brunt signed a voucher for M. Cahill who was making an application to become a fireman.

Based on the directories it would appear that John O'Brien moved from Red Hook to Carroll Gardens circa 1887

3. ☘Patrick O'Brien

   Brother of Ann O'Brien Costello and John O'Brien.

   Birth: Ireland

   Marriage:

   Children: Mary (Brady) and Thomas

   Death: Prior to the death of Ann O'Brien Costello

4. Michael listed in San Francisco, California in the propate papers of Ann O'Brien Costello

Ellen (Nellie) O'Brien

Born Brooklyn c 1857 niece or daughter of Ann O'Brien Costello. With Ann O'Brien Costello in several censuses. Who was she?

Conover corner Dikeman, 363 Van Brunt, 361 Van Brunt, and his wife, Catherine O'Brien

1870 Brooklyn Eagle Liquor dealer list Dougherty, D., CONOVER corner Dikeman

No #363 Van Brunt on 1886 map. 361 was on the north east corner of Van Brunt and Dikeman in 1886.

Daniel Dougherty was born circa 1842 in Ireland. He married Catherine O'Brien.

Birth: c 1842 Ireland.

Marriage: Catherine O'Brien

Children:

1. George c 1864
2. Arlian
3. Anne
4. Francis c 1869

1870 Dougherty, Daniel liquors Conover c Dikeman.

1870 census Dougherty, Daniel 28, wh liquor dealer $12,000 Ireland, Catherine, 22, New York, George 6, Arlian (?) 5, Anne 3, Frances 1

Dougherty, Daniel, liquors 1870, 1871 Conover c Dikeman

1873, 1874, 1876, 1877, 361 Van Brunt, Dougherty, Daniel, liquors.

1873 Daniel Doughtery of 3-1 Van Brunt "was aroused from his sleep by the cries of a servant girl on the floor above." He confronted a burglar who he chased through "several apartments". The would be thief had entered though an adjoining stable. "He crept through the widow of the stable, having first broken the iron bars in front."

1875: 316 Van Brunt frame $8,000 Daniel Dougherty, age 35, Ireland liquor, naturalized owner of property, Catherine age 30 born Kings, George son age 12, Eliza age 8, Adeline 7, Nne 5, Thomas 3

✟ 1876, Dougherty, 363 Van Brunt, Catherine beloved wife of Daniel Dougherty age 28, her brother Dennis O'Brien. Friday, February 11, 1876. (Dougherty, Catherine, 30 y Feb 10, 1876, 1427, Kings)

1880 Census: No.

Other O'Brien Records

Ann Collins 20 Apr 1854 30 Apr 1854 Michl Collins Catharine Ann Collins Birth Date: 20 Apr 1854 Baptism Date: 30 Apr 1854 Father: Michl Collins Mother: Catharine God Parent: thos o'brien God Parent: jo collins)

Collins, Michael (c 1820 - ), liquor dealer/barkeeper, Van Brunt near Williams, Home No. 8 Van Brunt

A Survey of Liquor Dealers in Red Hook mid to Late 1800s

Red Hook Liquor Dealers - The Families

Balfe - Ball - Baumann - Behnken - Bell - Black - Boysen - Bray - Brickwedel - Callaghan - Carberry - Cassin - Cavanagh - Collimore - Collins - Coogan - Cordes - Curran - Daly - Dawson - Dempsey - Depperman - Devan - Dixon - Dockery - Donovan - Doran - Ehrichs - Fay - Finkeldey - Fitzgerald - Garahan - Gillen - Graef - Haack - Henry - Higgins, Hugh - Higgins, George - Hoehn - - Hoffman - Hughs - Hunold - Hussey - Judge - Kassenbrock - Keleher - Knoop - Krohler - Kuhn - Lamont - Lever - Little - Looney - Madigan - Mahnken - McAvanny - McGee - McGrath - McKenna - McQuade - Meyers - Molloy - Mooney - Moran - Mullady - Munsinger - Murray - Noble - O'Hara - Oberdieck - Powers - Ropke - Schmadeke - Schwanemann - Shea - Sheridan - Siebe - Simmons - Struve - Sullivan - Weinphal - Winkelman