Album of Genealogy and Biography, Cook County, Illinois with Portraits 3rd ed. revised and extended (Chicago: Calumet Book & Engraving Co., 1895) - David Philip O'Leary (note: the Philip was for Philip Rogers, his Uncle), the accommodating Postmaster at Evanston, is a native of that city, born at what was then known as Ridgeville, later South Evanston, June 6, 1856. His parents were John and Margaret O'Leary, of whom further mention will be found elsewhere in this volume.  David P. O'Leary attended the public schools, and later a private school taught by Miss Frances Willard, whence he went to Notre Dame University, South Bend, Indiana, graduating from that famous institution in the Class of 1879.

Mr. O'Leary began business life as a reporter on a Chicago paper, in which capacity he continued for two years.  In 1884 he began dealing in coal at Evanston, and continued at that business ten years.  Upon the death of his father, he became administrator of the estate of the latter, which includes much valuable property along the lake shore, and is intersected by the famous Sheridan Road.

On the 1st of March, 1894, he was appointed Postmaster at Evanston, and still holds that position, discharging its arduous duties in a manner which wins the approval and admiration alike of political opponents and party colleagues. During the first year of his administration, he raised the Evanston office from the second to the first class, annexed South Evanston, and established the free-delivery system, increased both clerk and carrier force, and this office is now ranked as the third in the state.

Mr. O'Leary has been a member of St. Mary's Catholic Church of Evanston from youth.  He exerts a marked influence in the local councils of the Democratic party, has served as a member of the County Central Committee for the last twelve years, but has never allowed his name to come before the people as a candidate for elective office.  He is a gentleman of pleasing address and ample business capacity, and is constantly forming new friends among the people whom he meets.

Mr. O'Leary can relate many interesting reminiscences of the days when the greater part of Evanston was an unbroken wilderness.  While a boy, he and his father and brothers often helped to rescue people wrecked off Gross Point, then a treacherous shoal, on which many vessels were lost.  At that time the Government had made no provision for promoting the safety of navigation at this point, which extended much further into the lake than at present, and in stormy weather vessels frequently ran upon the adjacent shoals, and were broken in pieces by the wind and waves, leaving passengers and crew to save themselves as best they might.  Their only assistance was that afforded by the voluntary efforts of the families residing in the neighborhood, who did all in their power to aid the unfortunate people.  It was near this point that the ill-fated "Lady Elgin" was lost, with about three hundred souls, a catastrophe which will ever be remembered by many of the people of Chicago and Milwaukee.  Most of those who survived the disaster landed at Gross Point.

David Philip O'Leary interviewed Sept 30, 1900 about his father John - John O'Leary came to Chicago in 1836. Soon after he bought a farm of 40 acres at Sunnyside and lived there from 1837 to 1840. While living there many of those who settled at Evanston passed their house in teams. They stopped and made their acquaintances and when the O'Learys themselves moved to Evanston they found them settled on their various farms. Among them were Edward Murphy, John Carney, Hathaway and others. In 1837 John O'Leary bought 160 acres in Ridgeville (situated in part where Calvary Cemetery now is) and in part south of the Cemetery and north of the present Chicago city limits. In 1840 he moved to Ridgeville. In 1859 he sold 40 acres to Calvary Cemetery, this being the year the Cemetery was established. Long ago, Mrs. Lynch (Ellen O'Leary Lynch, a daughter of John O'Leary) relates, a great oak stood at close to the spot where the gates of Calvary Cemetery now are, and it was on the O'Leary's table, draped with the alter linens and placed under the canopy of the oak tree, that the first Catholic mass was offered within Evanston's boundaries. David Philip O'Leary, one of John O'Leary's sons, was born in Evanston. His middle name was given him for Philip Rogers, a neighbor (Note: Philip Rogers was also his uncle, being married to Mary Ward Masterson Hickey Rogers, the sister of Margaret Masterson O'Leary, David Philip O'Leary's mother.

Obituary (abt Jan 13, 1919 Chicago newspaper) - Funeral for Father O'Leary to be Tomorrow - Evanston Priest Had Interesting Career in Journalism, Business, Politics and Church - Death Was Sudden - Succumbs at Hospital to Attack of Pneumonia Following Influenza - Funeral services for the Rev. David Philip O'Leary, who died yesterday morning at St Francis hospital from pneumonia developing from influenza will be held tomorrow morning at 10:30 o'clock at St Mary's Church, Rev W P Smyth officiating.  Rev. O'Leary was born in Evanston in 1850 and while he was extremely active for more than 40 years in public life and the activities of the Catholic Church, he always looked upon Evanston as his home. Former Newspaper Man - His career was an active one. In 1868, after graduating from the University of Notre Dame, he entered newspaper work in Chicago. Finishing two years of journalistic work, he established a very profitable coal business in Evanston.  Though the deceased was never a politician, he was always active in political matters of import.  Upon the election of Grover Cleveland, he received an appointment and during Cleveland's term he received a reappointment.  Leaving the field of commercial endeavor, he began to study law, was admitted to the Bar in Illinois and for several years practiced in Chicago. Leaving a large and lucrative practice, he joined the faculty of the University of Notre Dame as an instructor.  He had scarcely completed a year on the Notre Dame faculty when he was appointed president of Watertown College. Giving up this position of responsibility, Rev O'Leary returned to his first ambition, which was to study philosophy and theology.  Became a Priest - Twelve years ago he received his appointment as a priest to the congregation of the Holy Cross, Notre Dame, Indiana at which work he remained until three weeks ago when though ill he took a leave of absence returning to Evanston to take over management of the O'Leary estate consisting of property south of Calvary Cemetery which was developed by his mother who died shortly before he commenced studying for the priesthood and made a trust with the Rev. O'Leary as Trustee at the same time he was acting as Chaplain for the Marywood or St. Scholastica Academy.  To take body to Indiana - The Rev. O'Leary was planning to wind up his affairs in Evanston and return to his former position in Notre Dame when he was taken sick.

Father Smyth's Tribute to His Departed Friend (abt Jan 13, 1919 Chicago newspaper) - Funeral of Rev. David P. O'Leary at St Mary's Attended by Hosts of His Friends - Solemn Ceremonial - High Mass is Celebrated by Church Dignitaries from Home and Abroad - "I have fought the good fight. I have finished the race," was the quotation from St Paul that Father H P Smyth opened a feeling tribute to Father David P O'Leary at the funeral services at St Mary's church this morning.  The open casket stood before the chancel at the head of the center aisle and the church was filled with mourning friends.  He was a very remarkable man," said Father Smyth. "He had fought the good fight and went to his reward smiling and contented, with no fear of death.  All his life he had done things well that he cared but little for.  A man of remarkable physical and moral courage, he had borne burdens for years that might have broken the spirit of a less well-equipped man. - Loyal to Country and Church - "He was loyal to the community, the county, the state and the nation and always devoted to the cause of the church. At almost the last he still cherished the hope of going back to his alma mater at Notre Dame to end his days.  When he left there, before he .... (lines are missing) .... that were forced upon him he always wanted to go back but it was not until twelve years ago that he was able to take up the work he most loved and was ordained to the priesthood. Family obligations that were not met until that time forced him to do work that was distasteful to him.  He was an independent man, full of the courage of his convictions, decided upon what he thought was right and given to expressing himself freely without regard to possible disadvantage personally.  I hope it may be found in his will that his expressed intention to provide handsomely for Notre Dame will prove true.  He wanted to do something for that institution." - That Runaway Accident - "Regarding the accident that was a factor in his death it may be worthwhile to tell the true story of that occurrence.  A horse that never had beem mistreated was badgered by a malicious boy until he ran away.  The sudden appearance of an automobile caused him to run again and Father O'Leary was compelled to jump from the buggy and fractured his good leg in five places.  For ten weeks he lay in a steel frame and then recovered sufficiently to be out.  Then influenza claimed him as the result of attempting to wade through some snow that he might say mass at St Francis hospital. Pneumonia quickly followed that and then the end." Impressive high mass services were conducted, the celebrant being Father Boyle of Notre Dame, the deacon Father Crowe of St Ita's and the subdeacon Father Feldheim.  Father McKeown of St Mary's was master of ceremonies and among the other priests in the chancel were Father Bierman of St Nicholas, Father Croke of St Andrews, Father Scanlan of Our Lady of Lourdes, Father Casey, and several from Notre Dame and Chicago. - Served a Luncheon - The soloist was Miss Esther Jennings and the pall bearers W. J. O'Connell, Daniel McCann, W J Hartray, M. M. Connery (is this one of our Connerys, maybe Michael Morgan Connery?) , Stephen Touhy (note from MH: his nephew) and William Y Quinlan. The sisters from St Scholastica, Marywood and St Francis hospital were represented.  The ladies of the Catholic Woman's club prepared and served a luncheon in the school hall to the officiating priests and those going to Notre Dame with the remains, the interment taking place there late this afternoon.