We are all familiar with the modern spectacle of funerals as immediate canonizations rather than occasions for prayer and penitence for the deceased. Contemporary discomfort with the doctrines of hell and purgatory—and a profound lapse in catechesis on the gravity of sin—has transformed funeral masses into a "celebration of life," in such a way that the bereaved are not enjoined to pray for the dead. Everybody just seems certain that grandma is among the choirs of angels and doesn't give it a second thought.
This approach is woefully uncatholic. It is terribly sad when you have an occasion where everyone is gathered together in memory of the deceased and they fail to take the opportunity to pray for his soul, often with the complicity of the parish priest. It is another example of how modern theological errors have corrupted even our view of death.
That being said, I have noticed that traditional Catholics are prone to erring in the opposite way, by acting like we can never assume someone has made it to heaven. There seems to be this attitude that we can simply have no clue one way or another; that Christians are meant to have a disposition of complete uncertainty when it comes to the eternal destiny of our loved ones. Confronted with the holy life and abundant fruits of grace of the deceased, at most they will venture to say is a timid, "I hope they made it," quickly followed up with, "but I will pray for their soul," lest their hearer assume they have adopted the heresy of universalism.
This is not a Christian attitude either. While we admit that there's always the possibility of secret vices (e.g. that our pious Grandma Doris was secretly a mule for the cartels, or daily Mass-goer Uncle Randy had a hidden gay lover), in general, the historic attitude has been that we can be assured of the salvation of those whose lives clearly manifest the work of grace, as demonstrated through their piety and virtues.
Church history is replete with such examples, not only among the saints, but among regular people whose lives manifested the fruits of a godliness. There are many written testimonies to this effect, but by way of example, I would like to present a letter written by Fr. Gaspar Meneses, Jesuit Superior at Vera Cruz, Mexico, addressed to his brethren in Spain announcing the death of one of their comrades, Fr. Juan Rogel, in January of 1619:
"At last good Father Rogel has reached the end of his labors and his temporal life, having spent sixty-five of his ninety years in the Society of Jesus. He entered two years before the death of our Blessed Father, St. Ignatius, being then at twenty-five a Master of Arts and a Bachelor of Medicine. From his entrance to his death he was an example to us all. Busied in ministrations to all sorts of people, his fervor and devotedness made him universally venerated and loved, and 'the saint' was the name thye gave him. He was a truly humble man; and from his humility, sprang a great spirit of obedience, even in an advanced age, which would ordinarily make it a burden...
Here in Vera Cruz since 1580, he was insatiable in his hunger for souls. Day and night he was in the confessional and teaching the children or the ignorant and visiting the needy and afflicted. Devoting himself especially to the poor and lowly and the Negroes, he attracted to his instructions people of the highest consequence, and he won the hearts of all, molding their lives for God.
...Chatting and smiling with his wonted joyousness at table, January 19, he abruptly rose from his chair with shining countenance, joined his hands, raised his eyes to heaven, and then turning smiling eyes upon his host as if to thank him for his charity, he closed them and was dead. His soul, we believe, had winged its flight to be at the Heavenly Table forever.
...His body was interred in a cedar coffin, the last offering of his honored host; his angel guardian, as we hold, had led his saintly soul to its Creator. I recalled what the Scripture said of Abraham, 'He died ina good old age, and being full of days was gathered to his people.' Father Rogel was one of the ancients of the Society and a venerable servant of God, and his holy life assures us that he is enjoying the clear vision of the Divine Majesty."
Fr. Gaspar Meneses, SJ
Vera Cruz, Jan. 29, 1619*
Fr. Juan Rogel is not a saint or even a blessed; to my knowledge, he has never had a cause opened. Fr. Rogel was simply a Jesuit priest who fulfilled his duties and lived a life of virtue. Because of this, his companions assumed he was in heaven and had no scruple about saying so.
Did Fr. Meneses and the other Jesuits pray for the repose of the soul of Fr. Rogel? I am certain they did, and herein lies the difference between the attitude of Fr. Meneses and today's Catholics. There would have certainly been masses and prayers offered for the repose of Fr. Rogel, not only in the days after his death but likely on the anniversary of his passing for many years. He would have also been included in the prayers and masses of the Society for its deceased members and benefactors as well. Fr. Meneses assumed Fr. Rogel had gone to heaven, but he understood that this did not absolve him from his responsibility to due his duty and see to the well-being of the dead. He understood that, despit ehis assumption, Fr. Rogel could be in Purgatory and in need of prayers. Modern Catholics are not so wise; if they are assured their loved one is in heaven, it is taken as a sign that nothing further need be done.
Modern Catholics also tend to assume a loved ones have gone to heaven regardless of what their external life was like. We see Fr. Meneses, on the other hand, grounds his assumption squarely on the incontrovertable, external evidence of piety demonstrated by Fr. Rogel. In other words, Fr. Meneses would not have made such claims about just anyone; he did so for Fr. Rogel because he had objective grounds for his assumption.
But the point is that it is not wrong to assume a pious deceased has gone to heaven, so long as it does not detract from our obligation to pray for them. If a person demonstrates all the external signs of living a life pleasing to God, we are right to assume he has received his reward. Christian virtue is not so interior, so secretive that it can't be observed. Faith blossoms into a great tree, so vast that "the birds of the air made nests in its branches" (Luke 13:19). In the case of Fr. Rogel, "his holy life assures us that he is enjoying the clear vision of the Divine Majesty." Such is it with anyone who lives and dies leaving such a wholesome example.
Is this ironclad logical certitude? No, of course not; but it is assurance—moral certainty. This is what the virtue of hope is supposed to give us. Hope is the virtue by which we desire heaven and expect to receive it; it anchors our faith to the expectation of reward. It is like proceeding down a road towards a destination: while we know it is possible to lose our way and go off the road, we also have assurance that, provided we stay on the road, we will reach our destination. Similarly, we can have confidence that, provided we sincerely avail ourselves of God's grace, we will reach our heavenly destination.
So, when our loved ones die after a life of piety, let us pray and have Masses said for their soul, but let us also maintain confidence in our Lord's promise "Blessed are the pure in heart, for they shall see God" (Matt. 5:8).
*The letter of Fr. Gaspar Meneses can be found in its entirety in Michael Kenny, The Romance of the Floridas (New York: AMS Press, 1970), pp. 303-305