Simony is one of those medieval sins that has lost favor in modernity, even though anyone who has turned on the 700 club late at night could bear witness to exactly the sort of religious swindling and snake oil salesmen Dante castigates in this circle. The term derives from Simon of Magus, who not so coincidently is introduced in the first lines of Canto 19. Simon was mentioned in Acts as the man who approached the disciples Peter and John and offered them money in exchange for giving him the power to impart the Holy Spirit in anyone he touched. In medieval times, this process was practiced in the infamous practice of indulgences (i.e. corrupt clergymen offering to erase sins from the soul for a not so modest fee). You see examples of this in the never ending slew of religious informercials promising a vial of "blessed" water from the river jordan or a jar of earth from Jerusalem to help purge the sinner of his transgressions, all for the low low price of what$v$r. In fact, most of the shtick that the televanglists perform could be contrued as an act of simony.
Dante, in all his poetic irony, has crafted a devious punishment for Simon and his like minded crew. He and Virgil come across a series of small pools, made to look like baptismal basins popular in San Giovanni at the time. The sinners, though, are immersed upside down. Their feet are afire, and they are writhing in agony so much that "they would have severed withes and ropes of grass". The sinner writhing with the most vigor is Pope NIcholas III, whom Dante obviously believed to be guilty of simony, but who in actuality wasn't the worst guy, having settled a division between more moderate and extreme branches of the Franciscan order and worked tirelessly to help the poor. When Dante approaches him Nicholas actually mistakes him for the contemporary pope of Dante's time, Boniface. He says something interesting, proclaiming that the book has lied to him by several years, revealing that at least some of these sinners have been privvy to the fates of those not passed on to the afterlife yet. It is safe to assume that Dante believes Boniface is headed towards this particular circle of Inferno. But it does lead to an interesting rumination. By this reading, Dante believes that people's fates are fixed. There is no free will. But if that were true, why exactly is he going on the journey. He is lost, he knows he needs to transform his desire. But if its already been written in "the book". isn't it a pointless endeavor (unless, of course, the fates have already preordained his transformation of desire, placing him in whatever circle of inferno purgatorio or paradiso he is destined for and this journey is part of him fulfilling his destiny.)
So where does Dante land in the afterlife. There's a whole doctoral thesis for you, one that cannot really be answered (as if most of them can be).
All of this talk of simony reminds me of the pardoner's tale from Chaucer's Cantebury Tales. Chaucer was a huge Dante fan and there are certainly echoes of his masterpiece in Chaucer's own masterpiece. It is such a saucy read, especially in the prologue, where the pardoner boasts repeatedly of swindling poor souls he believes are undeserving of salvation, and thus his stealing money from them is quite justified. He repeatedly makes use of the biblical phrase "money is the root of all evil", al the while continuing to amass more and more money from these unfortunate and gullible souls. He is devilish in his doings, and yet he is a fairly interesting and complex character, knowing full well the dastardly nature of his trade. If you haven't read the Cantebury Tales, i would highly recommend it, especially if you have digested the Divine Comedy and are yearning for more. It is also extremley funny at times, which is a welcome break from Dante's unrelenting seriousness.
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