1923 – 1925: Fr. Francis H. Pennylegion, First Pastor

February 20, 1923
Archbishop Neil McNeil, writing from New York City, established the parish of St. Charles for the “Moore Park” section of Toronto, and appointed Fr. Francis H. Pennylegion as its first pastor. It was Fr. Pennylegion’s first pastorate.
Late February/Early March 1923
Fr. Pennylegion changed the name of the parish to St. Catherine of Siena (1347-80), in honour of an Italian mystic and diplomat and a member of the Third order of the Dominicans, who was canonized in 1461. Mass began to be celebrated in St. Charles School, a two-room brick building constructed in 1881. Located on Yonge Street below St. Clair, on the south side of the roadway leading into St. Michael’s Cemetery, it was the second school on the site. The original school was a one-room frame structure built around 1856. Both had been erected by St. Basil’s parish, whose northern boundary was then York Mills.
Summer 1923
The Archdiocese officially took over St. Charles School for a chapel. (A new school for the parish had opened on Garfield Avenue in January 1923.) Renovations and an addition, designed by architect Arthur W. Holmes, were made to the old school at a cost of $4,620. In August 1923, the parish borrowed $350 from the Archdiocese to pay for pews, kneeling benches and a confessional, purchased from Newman Hall; the St. Catherine’s Ladies’ Auxiliary paid off the debt in two years. High Mass was sung for the first time on October 7, 1923.
September 1925
Fr. Pennylegion resigned from the parish. In 1926 he became the founding pastor of Blessed Sacrament parish in north Toronto.
1925 – 1930: Fr. Francis J. Morrissey, Second Pastor
September 8, 1925
Fr. Francis J. Morrissey, D.D. was appointed the pastor. Fr. Morrissey had been a professor and vice-president at St. Augustine’s Seminary. He immediately changed the name of the parish to Our Lady of Perpetual Help, and began the search for a permanent site church and an architect to design it. The Archdiocese purchased property from the Gibson family at the northwest corner of St. Clair Avenue East and Clifton Road; the deed was dated March 1, 1926.
June 30, 1929
The Archdiocese and the contractor, Witchall and Son, signed the agreement to build the church. The typed estimate gave the cost as $152,000, but this was subsequently changed in ink to $154,952. J. Gibb Morton, a well-known Toronto church architect, was engaged to design the church. He chose the Neo-Romanesque style with a Byzantine flavour. Credit Valley variegated course stone with a rock face was used for the exterior walls, and dressed stone for the trim. Morton made provision for bells to be installed later in the 130-foot campanile. Bells have yet to be installed.
August 15, 1929
At 3:30 p.m., on the Feast of the Assumption, Archbishop Neil McNeil officiated at the laying of the cornerstone. A short dedication service at the place where the altar would be located preceded the cornerstone ceremony. Fr. C.S. Belisle, C.S.B. delivered the address.
March 18, 1930
Fr. Morrissey resigned from the parish and the Archdiocese. He transferred to the Diocese of Raleigh, North Carolina where he served as a chaplain at Duke and North Carolina universities.
1930 – 1953: Msgr. William A. Egan, Third Pastor

March 25, 1930
Fr. William A. Egan was appointed the pastor. The church was under construction, with rising costs and the stock market crash greatly reducing the invested parish funds. The debt inherited by Fr. Egan was estimated to be between $250,000 and $300,000, said to be the largest in the Archdiocese. He saw his pastorate as one of nurturing the spiritual growth of the parish and paying of the massive debt. Through his business acumen and fiscal conservatism the debt was paid off in 20 years.
June 15, 1930
At 11:00 a.m., Archbishop Neil McNeil presided over the opening and blessing of the new church and celebrated the first Mass. The Solemn High Mass was sung, accompanied by the choir of St. Michael’s Cathedral directed by Fr. J.E. Ronan, Rev. Dr. Leo O’Reilly of St. Augustine’s Seminary delivered the morning address. In the evening at Solemn Benediction the speaker was Fr. S.A. Corrigan of St. Mary’s Cathedral, Kingston.
April 4, 1937
The new organ was officially inaugurated when, the Catholic Register reported, “the church was filled almost to capacity”. Healey Willan, the distinguished composer, organist, choir director and educator, played the new organ, and Fr. J.E. Ronan spoke about the role of music in the liturgy of the church. Solemn Benediction followed. The organ was a Franklin Legge-Eaton instrument built in 1905 for the People’s Church on Bloor Street East. The church bought it for $5000 on the recommendation of Dr. Willan.
December 3, 1937
Archbishop James Charles McGuigan ordained six men of the Scarboro Foreign Mission Society at the church. One was an OLPH parishioner, Fr. John H. McGoey, S.F.M. His mother lent the family’s living room rug to cover the terrazzo floor in the sanctuary. After the ordination, Mrs. McGoey remarked that it wasn’t the first time she had seen her son lying on the rug.
April 22, 1946
Fr. Egan was invested in the robes of Domestic Prelate, with the title of Rt. Rev. Monsignor.
Late 1940s
The first large stained glass window was installed in the nave. The Annunciation was the work of Marjorie Nazer, a textile designer and stained glass artist. Many parishioners did not like the window, finding it too “modern”. Nazer’s commission was cancelled even though she had completed the sketches for the other five windows. The firm of Thomas G. Browne Church Interiors decorated the interior; a highlight was a painting of the Crucifixion in the domed ceiling of the sanctuary.
1952-53
The rectory at 78 Clifton Road was demolished and a new rectory, designed by architect Robert A. Servos, was built on the site. During the demolition and reconstruction, the clergy and the domestic staff resided at 57 Rose Park Drive, a house owned by the church. The new rectory cost about $120,000, half of which was raised by a parish building committee established for that purpose.
March 1, 1953
Msgr. Egan died at age 76. He did not live to see the completion of the new rectory.
1953-1978: Msgr. Lucius F. Barnett, Fourth Pastor

September 9, 1953
Fr. Lucius F. Barnett was appointed pastor, and arrived in the parish on September 12. It was his only pastorate. Fr. Barnett had been a professor at St. Augustine’s Seminary, and had held several key positions on the Toronto Marriage Tribunal.
1955-1965
Five large stained glass windows, designed by F. Mayer of Munich, were installed in the nave. Several smaller stained glass windows were installed throughout the church and in the sacristy.
September 9, 1957
Fr. Barnett was invested in the robes of Domestic Prelate, and on September 28, 1957 was appointed Vicar Forane (Dean) of North Toronto. In 1970 he was elevated to Prelate of Honour.
1960
Architect Harold Rambusch of New York City designed a major renovation of the church, in association with Roy Orlando of Toronto. Highlights were the marble altars, communion rail and baptistry, and the lindenwood statues of St. Anthony, St. Anne and St. Joseph. Also installed were the gold-leaf carvings of the Statues of the Cross, the large medallion of Our Mother of Perpetual Help, and the massive light fixtures. Rambusch and Orlando also renovated the sacristy in 1961.
Around 1965
The carving of Pontius Pilate was stolen from the first Station of the Cross. The replacement did not quite match the other figures in scale or finish, nor was it as imposing a figure of authority.
1972
The sanctuary was renovated. A new freestanding marble altar table was built, and the old altar was redesigned to become the Blessed Sacrament altar.
June 10, 1973
The parish celebrated the 50th anniversary of its founding by inviting Archbishop Philip Pocock to celebrate a Mass of Thanksgiving and deliver the homily. No other functions marked the occasion.
September 12, 1978
Msgr. Barnett retired, 25 years to the day of his arrival in the parish.