Judas' betrayal was not his most serious sin

One of my favorite songs is a wistful jazz ballad called “When October Goes”. The lyrics were written by Johnny Mercer and then sat in a desk drawer for a decade or so until Mercer’s widow handed them off to Barry Manilow. Manilow put the words to music and the result was a poignant ode to days gone by, with a final note that haunts the listener long after the song has ended. If you’ve never heard “When October Goes”, then I recommend you listen to the 1991 recording by late jazz great Nancy Wilson. She sings it from the heart.
I think about this song every year around this time because it captures in words and music the unique, melancholic beauty of autumn which, as Catholics, we experience most deeply as October fades into November. During the three days spanning October 31 and November 2—Allhallowtide—a somber veil cloaks the Church as we honor the souls of those who have passed before us—saints and sinners alike.
I made an effort to learn about the history of this three-day observance the first year I taught CCD. I wanted the kids to understand that there is more to Halloween than costumes and candy. More importantly, I wanted them to recognize the fact that Halloween is just a lead-in to the real holidays of All Saints and All Souls. Whether the kids actually did gain a more mature appreciation of Allhallowtide is open to debate; but what I can say with certainty is that I did.
I won’t recount here everything I’ve learned about Allhallowtide; but I will clarify that All Saints Day did not originate as a pagan harvest-time celebration that was coopted by the Church and given a more solemn spin. Catholics have been honoring the saints since the 7th century A.D. However, the holy day at first had been celebrated on May 16th, the anniversary of the date on which Pope Boniface IV in 609 A.D. converted the Parthenon to a church and dedicated it to the Blessed Mother and all those saints who had died for their faith. A little more than a century later, Pope Gregory III moved the holy day to November 1st, expanded it to include all saints, gave it the name by which we know it today, and incorporated it into the official Church calendar. According to some, Gregory transferred the date of All Saints Day to correspond with Samhain, the Celtic festival of the dead, which may be why the holy day has mistakenly been thought to be of pagan origin.
Over the next two centuries, All Saints Day gained in popularity while enthusiasm for Samhain began to dwindle. By the 10th century A.D., the Church instituted All Souls Day on November 2nd. The closer similarity to Samhain was more attractive to the yet-to-be-converted Celts, and thus eventually replaced the pagan festival.
All Souls Day 2020 will be especially somber due to the far too many lives we’ve lost this year. The narrow path has become very, very crowded; and it is our responsibility as Christians to facilitate a speedy passage for those who travel it by offering our sincere and hope-filled prayers. We cannot return to life those who have departed from us; but we can take comfort in the new and better life that awaits them.
That promise of new life with Our Father in heaven is the diamond in the coal mine, the bright light amidst the solemnity of Allhallowtide. We wouldn’t pray to the saints if we didn’t think they could hear us. We wouldn’t pray for our loved ones if we believed they were irretrievably lost. As paradoxical as it may seem, there can be joy in sadness. Our faith gives us hope and affirmation that the pains and troubles of this world are only temporary. Perhaps that’s why we sometimes allow ourselves to partake in sentimental nostalgia or enjoy a wistful, autumn love song that we know will make us cry.