If both died in a state of unrepented mortal sin, neither of them has any chance. If both died in a state of grace, both will certainly enter heaven. All souls which depart this life in a state of grace will eventually enter heaven. However some souls need more purification in purgatory than others. The question, then, is whether the wealthier man will secure the more rapid purification, and enter heaven more easily than the poor man. Not necessarily. The $1 may easily have been the greater generosity relatively than the $1,000. The dispositions of the poor man could easily have been more pleasing to God than those of the rich man. The very poverty and suffering of the poor man in this life was already expiation; so much so that Christ practically says that heaven belongs almost by special right to the poor, declaring that the rich with their life of comfort and self-indulgence will enter heaven with great difficulty. The poor man might scarcely need the few Masses he asks, whilst the rich man, with all his Masses, may have far more to expiate. Then, too, the departed can benefit by Masses and prayers within certain limits only. Anything over and above those limits would be applied to other souls. St. Augustine clearly taught in the 4th century, “There is no doubt that our prayers can benefit those who so lived as to deserve to be benefited by them.” He recommends sacrifice on their behalf, whether of the altar, or of prayers, or of almsgiving, adding, “Although they do not benefit all for whom they are offered, but those only who deserved during life to benefit by them.” But we can safely leave the adjusting of all these things to God.
Radio Replies Volume 1 by Rev. Dr. Leslie Rumble MSC and Rev. Charles Mortimer Carty