Symbols have a way of escaping the intentions of those who use them. A Catholic himself, and a vocal critic of Obama's public policy, Scalia most likely wore the hat as a silent protest against Obama's presumptive exercise of Presidential authority. On this reading, Obama assumes the role of Henry VIII, who usurped the spiritual authority of the church by making himself head of the English Church. Scalia plays the part of More, whose protests earned him a martyr's crown, and, in due time, sainthood.
There is a second possible way to interpret Scalia's actions, albeit a much less likely one. It has to do with his claiming common cause, not merely with a political martyr, but with a bonified saint enrolled in the ecclesiastical calendar of the Catholic Church.
It is remotely possible that Scalia has absolved Obama for his outrages against both himself and God's church. That's what saints who are martyred do--saints like Saint Thomas More. They swiftly forgive their executioner, commend the souls of all present to God, and patiently wait for the axe to fall, the hammer to drop, the rope to snap, or what have you. That's what Christ did in Luke 23, as he hung on the cross.
Let's explore the later possibility just a little further, just for the sake of argument.
The renaissance scholar Desiderius Erasmus' In Praise of Folly (Moriae Ecomium) is usually published with a letter written to More. The letter is a reflection on the apparent etymological connection between Folly and More, which is still preserved in our word moron. The letter commends Erasmus' panegyric on folly the protection of More, against its detractors, who mistook its praise of folly for a frivolous defense of idiocy.
The wisdom of Folly:
"Briefly, no society, no association of people in this world can be happy or last long without my help; no people would put up with their prince, no master endure his servant, no maid her mistress, no teacher his pupil, no friend his friend, no wife her husband, no landlord his tenant, no soldier his drinking-buddy, no lodger his fellow-lodger -unless they were mistaken, both at the same time or turn and turn about, in each other."A dose of foolishness helps us bear with each other.
If Scalia did laid claim to the foolish saintly aspect of More's legacy, he is entirely unjustified. Peter Ackroyd's The Life of Thomas More beautifully chronicles More's the inner turmoil as he groped to understand whether obedience to the king was necessarily disobedience to God.
When he had made up his mind to oppose the king, More determined to let the ways of the world to have their way with him. He is even recorded to have said to his executioner, 'Thou wilt give me this day a greater benefit than ever any mortal man can be able to give me. Pluck up they spirits, man, and be not afraid to do thine office. My neck is very short: take heed, therefore, though strike not awry for saving thine honesty.' Much like Christ, again, who goes willing to the cross.
This kind of foolishness Scalia most likely did not intend. If indeed it was a replica of More's hat that sat on his head, his symbolic appropriation debases the memory of More's saintly martyrdom. In death, saints do not so much confront the worldly powers with another worldly power sanctioned and 'sanctified' by a Church. In their own persons, the demonstrate the futility of all worldly exercises power, including their own. Saints transcend mere political grandstanding, however subtly that is enacted.
Justice Scalia is not a this kind of moron. That's why, we can hope, it wasn't More's hat he was wearing.