About Teddy's letter to the pope
1. The great majority of Teddy's letter (aside from the platitudes) strikes me as an exercise in self-justification.
2. A small part of the letter, however, could be construed as expressive of some level repentance and of a desire to be reconciled with the Church: "And though I have fallen short [in my efforts to be a faithful Catholic] through human failings I've never failed to believe and respect the fundamental teachings of my faith. I continue to pray for God's blessings on you and on our church and would be most thankful for your prayers for me."
Obviously, Teddy's language here does not demand such a generous interpretation, but it would support a plausible case being made for same.
3. That said, looking at it alone, I doubt that this letter (which was not made public till after the funeral Mass), sufficed canonically as a "sign of repentance" sufficient to win Kennedy a Catholic funeral, for there seems to me little actual repentance expressed in it, and whatever was expressed (to the pope) seems inadequately conveyed to count precisely as a "sign" of repentance for the wider community. No, Teddy's request for Catholic funeral was licitly granted on other evidence, as I have argued elsewhere.
4. But if I made add one more observation: Recall that the letter was written at least six weeks before Kennedy's death. Now, if one were to describe Teddy qua Catholic politician as the paradigmatic man who over many decades has dug himself into a dreadfully deep pit, then one might see in his letter some indications that Teddy has at least stopped digging, and that he might even be coming to sense that he needs help from his Church in climbing out again.
If that's true, then another six weeks of terminal brain cancer, spent apparently lucidly, might have spurred Teddy toward the means to escape from his past that all good Catholics want to see for him. The pope obviously did not want to crush what might have been the smoldering embers in Ted's letter and so, I think, despite his having precious little to build on, the pope nevertheless answered Teddy's letter and asked God grace upon him.
Whether Teddy in fact repented is known to him and God alone (and, I repeat, the fact of repentance is not an issue in the decision to grant a manifest sinner an ecclesiastical funeral), but I wonder whether his letter might not, at the end of time, be seen rather like the arrogant but utterly lost driver who, after so many hours of driving the wrong way, finally pulls over and considers asking for directions. + + +
Some other interesting posts:
1. Mark Brumley on "Signs of Repenance or of the Status Quo"
2. Carl Olson on "The funeral and the letter"
3. A longish exchange on Kennedy's right to a Catholic funeral