Carmela Marocchino lived near the friary at the house of Mary Pyle, the American who had become his disciple. Carmela's brother, Padre Vittore, was a beloved priest until his sudden death in January of 1958. Wondering if he had saved his soul, she went to Padre Pio a few days later. She began to cry, and so did Padre Pio. She asked the Padre why the Lord had taken her brother. He explained that the Lord entered a garden where there many beautiful flowers. Walking over to the most beautiful flower of all, he picked it. This is exactly what happened to Padre Vittore. Carmela then asked if her brother was saved. Padre Pio answered in the affirmative, but added that we must pray.
Some months later, hoping that Padre Vittore would now be in Paradise, she asked Padre Pio in the confessional if her brother was now in heaven. He replied, “My daughter, we priests have more responsibility before God, and when we appear before Him, it is with fear and trembling. Therefore, let us pray.” Then, about a year after her brother's death, she again asked Padre Pio about him. This time his answer was, “He is in Paradise.” Carmela was overjoyed. But she began to consider that even though he had been a priest, and was a student of Padre Pio's, he still had to spend 11 months in Purgatory. This was because of the responsibility of so many souls under his spiritual direction.
On yet another occasion, Carmela asked Padre Pio if she should still pray for her deceased parents. He replied, “Even if your parents are in heaven, we must always pray. If they no longer need prayers, they are applied to other souls.”
One time in 1949 Padre Pio was talking with a certain doctor who was very close to him. They were discussing prayers for the dead. Padre Pio said to him, “Maybe you don't know that even now I can pray for the happy death of my great-grandfather!” But the doctor remarked that he has been dead for many, many years. Then Padre Pio explained, “For the Lord the past does not exist. Everything is an eternal present. These prayers had already been taken into account. And so I repeat that even now I can pray for the happy death of my great-grandfather!”
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Based on accounts in Padre Pio Mistero e Miracolo, by G. Giacometti and P. Sessa, pp. 225-35, and also The Holy Souls, by Padre Alessio Parente, pp, 103-104 and pp. 177-179.