Well, golly. It seems like one can play this game forever. Steven E. Landsburg, a professor of Economics at Rochester, penned a piece for Slate entitled "Hail to the King," in which he likens a) Jimmy Carter to Henry VI, b) Ronald Reagan to Edward IV, c) George H. W. Bush to Richard III, and d) Bill Clinton to Henry VII. (Thanks to the Newstok article for the link.)
Because Landsburg is writing in 1999, he attempts to predict who will be our Henry VIII. The punch line is good:
"If history repeats itself, we ought to be able to figure out who's destined to succeed Bill Clinton in the White House. Henry VII was followed by Henry VIII, a man best remembered for his gargantuan appetites, his dissipative lifestyle, his troubled marriages, and his rocky relationship with the Catholic Church. The message is clear. Ted Kennedy, your time has come at last."
Gerard Manley Hopkins and Shakespeare
3 hours ago