Woolsey, charged in a lawsuit with swindling $490,000 from Cale, met her a few years ago when she was in a dispute with her former parish, St. Jean Baptiste on East 76th Street.
Cale had donated $10,000 for renovations, and in return wanted the church to install a small plaque honoring her family, said the colleague, a church official who didn't want to be named.
When the church refused, Cale complained and took up the matter with Woolsey, co-vicar of Catholic churches on the East Side of Manhattan.
Amid her dispute with St. Jean Baptiste, Cale's brother Dominick died and even though she wasn't a member, Woolsey let her have a burial service at his church, St. John the Martyr on East 71st Street, said the official.
Woolsey also helped Cale get back her $10,000 donation to St. Jean Baptiste so she decided to stick with his church.
Cale often sent envelopes with money to the parish's priests, said the official but the checks were made out to the priests, not the church.
Also, Cale regularly brought meals to Woolsey including his favorite dish, broccoli rabe.
They grew closer after Woolsey's mother died.
"He became a son to her," said the church official. "He took on the obligation of a son, and she began calling him at all hours of the day."
A St. John the Martyr parishioner, Flora Aponte, confirmed that Cale and Woolsey were close.
"He never asked for money, but it was her wish to give him money," said Aponte.
Woolsey recently underwent heart surgery, and has been advised not to discuss the matter, said the church official.