Widely respected and even more widely admired, Msgr. Kevin J. O'Leary, who is best known for his 18-year tenure as rector of the Metropolitan Cathedral of the Holy Cross, became a senior priest of the archdiocese on May 1, 2026.

Born in Boston on May 21, 1951, a son of the late William and Barbara (Horgan) O'Leary, he has one brother, Mark, and three sisters, Jane, Pamela Hennessey, and Susan Coghlan.

Raised in the strongly Irish Catholic environment of South Boston, he attended Gate of Heaven grammar school, where he was an excellent student. He came to know, admire, and esteem the Sisters of St. Joseph of Boston who were the faculty. To this day, he can rattle off the names of his own teachers, as well as those assigned to the schools who were not his teachers.

He has a seemingly bottomless store of narratives from his elementary school days, and really from his whole life. Those who know him well will tell you there are certain key words or phrases, now called "triggers," which inspire a telling of the story. As those who have heard them will attest, as incredible as they sound, they must be true because no matter how many times they are told or how many years pass, they are the same.

Following his elementary school days, his grandmother, who raised him because of the early death of his mother, had arranged for his attendance at Catholic Memorial High School in West Roxbury, telling him about the Brother Rice Christian Brothers "The best teachers in Ireland." He was reluctant about attending, but her incentive gift of a new car to get him across the city from Southie to CM soon removed any "second thoughts."

Following high school, he was enrolled for undergraduate studies at St. Louis University, the Jesuit university in eastern Missouri. His undergraduate major was French, which got him to a semester abroad in France; he especially enjoyed time in Brittany.

At St. Louis, he recalls the influence of the Jesuit priests on the faculty. He remembered with great affection Father Rosario Mazza, SJ, who "was a tremendous witness to the faith. He was kind, sympathetic, and had a brilliant mind." The initial inklings of a priestly vocation were there, but he waited 15 years before taking a leap.

During the 15 years, he was an educator at area Catholic schools, including St. Brendan, Dorchester; back home to Gate of Heaven; Newton Country Day of the Sacred Heart; and principal at St. Mary School, Quincy; and at St. Catherine of Siena, Norwood, then one of the largest schools of the archdiocese.

Father Kevin G. Toomey, now a senior priest, told The Pilot, "When I was newly ordained and assigned at Gate of Heaven, he was on the faculty. He was an excellent teacher. He ran a tight ship in the classroom and always showed himself serious about the classroom."

While the classroom was important, it was at these schools that he developed some extracurricular projects, which he brought with him to parishes. Two are still current: Christmas Cantata and Christmas Bazaar. The bazaar is self-explanatory; the Cantata was a whole production around the Nativity, complete with music, costumes, and participation by every student. Prized students got Joseph and Mary, and the youngest would be angels and even several appearing as sheep. It was a living creche.

He initially entered St. John Seminary, Brighton, for theological studies, but after a couple years, stepped back "to be sure." Returning to seminary, he was now at Pope St. John XXIII National Seminary, Weston, where he completed his studies. As he said of it: "I loved it. And I especially appreciated the guidance of Msgr. Francis Kelly (seminary rector). He was a second father to me."

Bernard Cardinal Law ordained him to the priesthood at Holy Cross Cathedral on May 20, 1995.

His first assignment was as parochial vicar at Our Lady of the Assumption Parish, Lynnfield. He was happy here, the happiness was increased greatly because of the presence of a parochial school. The Cantata was refined and expanded.

In 2000, he was appointed parochial vicar at St. Mary of the Nativity in Scituate. Although there for only 18 months, he thoroughly enjoyed it and, yes, again the Cantata.

At the end of the first year of the new millennium, Bernard Cardinal Law appointed him pastor of St. Peter Parish, Cambridge. Renovations in the church had been previously completed, but the rectory and the school needed some attention. He deftly and rather quickly set about and completed both. During his seven years there, he also inaugurated a "Potato Mass," as he called it. Usually in conjunction with St. Patrick's Day, the "Potato" served as a reminder of the blight that brought such devastation to Ireland in the 1840s and spurred the emigration in the thousands from the Emerald Isle to the United States. He was vicar forane of Vicariate IV of the Central Region. Then-Regional Bishop of the Central Region Robert Hennessey said, "He was a very good pastor. He also helped with our regional meetings for the priests. Great host, great organizer."

His last assignment was as rector of the Metropolitan Cathedral of the Holy Cross, which was effective on July 1, 2008. This happened to coincide with the bicentennial of the establishment of the archdiocese.

Much work was needed on the physical structure of the parish's buildings, the cathedral itself, its schools, the rectory, which was now serving as the residence of the archbishop, and the nearby St. Helena House Residence.

With energy and zeal, he set to the task, raising funds for the various projects associated with each need. He grew the parish in numbers: Mass attendance, adding language groups; and in sacramental statistics notably of baptism and marriages.

The restoration of the mother church of the archdiocese certainly stands as the capstone of his tenure at the cathedral. In close contact and collaboration with Cardinal Seán P. O'Malley, he started from the ground up. He started from the roof and outside, then from the ground up. Roofing, pointing, structural needs discovered in the process were all addressed and completed before the lower church was divided in half. A substantial daily Mass chapel in the front half; then several larger meeting rooms, much needed and expanded restrooms, and parish offices took the back half, that closer to Washington Street.

While this was happening and before and during the restoration of the upper church, he was also a member of the Clergy Personnel Board, the Presbyteral Council, and the College of Consultors, and vicar for Vicariate III of the Central Region.

The major aspect of the restoration certainly was the upper church.

Everything was removed. What could be restored and reused was. What needed replacement, notably the pews, was. A new altar and ambo and the relocating of the cathedra (bishop's chair) was. The sanctuary was greatly expanded, which was especially significant since this allowed for ready participation by the assembly in liturgies, especially ordinations.

Lighting, HVAC, and sound systems and new means for live television broadcasting of the parish and diocesan liturgies were installed. New flooring throughout the cathedral and much needed repainting brightened the whole church beyond what many could ever recall. The classic stained-glass windows were removed, releaded, and reinstalled. Outside lighting focused visitors in the evening towards the mother church.

And, yes, the Christmas Bazaar and the scaled-back Cantata were still alive.

With the help of parish staff, he started to make the cathedral a center of archdiocesan life, not only the annual liturgies of Chrism Mass, ordinations, presentation of Cheverus Awards, Rite of Election of the OCIA; but other occasional, installation of new members of the Order of the Holy Sepulchre of Jerusalem and Order of Malta.

The cathedral rectory was also a place that welcomed visitors, often those of Cardinal O'Malley, but other times priests of our archdiocese and even beyond were invited to the nicely renovated residence.

On March 20, 2019, Cardinal O'Malley announced that Pope Francis had named Father O'Leary a member of the papal household as a Chaplain of His Holiness, with the title of "Reverend Monsignor." He still refers to himself as Father O'Leary but never corrects if you call him Monsignor.

With the arrival of Archbishop Richard G. Henning and the coincidence of Msgr. O'Leary's 75th birthday, he asked to be granted senior priest status. Giving him much needed relief from parish administration and giving the archbishop the opportunity to make his own appointment for the cathedral rector.

His new residence is in a familiar place, St. Brigid, South Boston. Father Robert E. Casey, the pastor of Msgr. O'Leary's home parish, Gate of Heaven, and of St. Brigid invited the Gate's famous parishioner back. He's delighted to be "home."

The move took sometime after May 1, 2026, as "We had to do some refurbishing of the rooms that would be his," said Father Casey. The move also required a bit of downsizing, though Msgr. O'Leary made sure he took some treasures he collected along the way. Among these, some Irish items, a few Hummels, and an icon of the Mother of God with the Greek inscription Theotokos that he received along the way.

And the Christmas Bazaar and the Christmas Cantata are back to where they started. The Bazaar is slated for Dec. 12 at Gate of Heaven; and the Cantata with the delighted cooperation of South Boston Catholic Academy closer to Christmas. Friends have asked Father Casey, "Are you ready for the "Potato Mass" in March?

If you see Msgr. O'Leary, certainly congratulate him on his new senior priest status. Refrain completely, however, from using the word "retired"