Glenn's already linked to it, so you've already read it, but as the Pope lies ailing
near death, I think this post by Hugh Hewitt does an excellent job of placing John Paul II into the context of 20th century history:

Such an outpouring of deep sorrow I don't think the world will have seen since Churchill died.

With Reagan and Solzhenitsyn, John Paul II represents the three forces of opposition to communism that shattered the evil empire, the Soviet Union --the American-led West, the Eastern European resistance, and the Russian dissident movement. They also represented the three spheres of opposition: political, artistic and spiritual. Each man came into the field of his greatness later in life, and each has endured hard circumstances in their later years. I hope Solzhenitisyn is able to and inclined to write about his colleagues in the struggle that triumphed.

Update: Orrin Judd links to this exceptional editorial in the Australian:

John Paul II has loved God, but he has also loved human beings and regarded each human being as sacred and imbued with innate dignity, and above all deserving of freedom. His remarkable personality was forged in the crucible of the two monstrous ideologies of 20th-century Europe - Nazism and communism. He detested both, he resisted both, he understood both.

What an optimistic and resilient spirit it must have taken to begin studying for the Catholic priesthood in Poland in 1942. But no sooner was the Nazi nightmare over for Poland than the communist nightmare began. It is probably for his role in the downfall of communism that John Paul II will be most obviously remembered. Poland became at one moment the pivot of Europe, and for a time the pivot of history. It was John Paul II's instinctive and sustained support for the Polish trade union movement, Solidarity, and its exuberant and brave leader, Lech Walesa, that was critical in leading to the downfall of communism in Poland. And this in turn had a mesmerising effect on the rest of Eastern Europe. The iron curtain of Stalin's tyranny and despair, which had hung across expanding swaths of Europe since 1917, was torn back as much by the Pope as by any other individual. Indeed, with Ronald Reagan and Lech Walesa, the Pope formed an astonishing triumvirate, allied in the common cause of human freedom and human dignity.

In many ways John Paul II has been the first wholly modern Pope. Nazism and communism were quintessentially expressions of a deformed modernism and this the Pope understood profoundly. His adroit leadership during the fall of the Polish communist government answered forever Stalin's sneering question: "How many battalions has the Pope?" The Cold War seems a long way away now, but it is right to pause to remember the radical evil that communism, the true ideological twin of Nazism, represented and the immense historical project involved in its consignment to the dustbin of history.

This is not the only political challenge the Pope has had to manage in his long reign. He has always been the friend of freedom, denouncing apartheid, opposing dictatorships and yet doing so in a way which would not increase the persecution of innocent people. But of course the Pope has not seen himself primarily as a political figure. Nor would it be fair to evaluate him as such. He has been, in his own words, a sign of contradiction, a great paradox of a leader. For his kingdom was not of this world. He has always believed in the importance of this world because of its relationship to the higher order of the spiritual world. In that sense, the Pope has been two separate leaders, an astute political figure central to the power equations of his time, and a deeply contemplative and intellectual spiritual leader, whose criterion of judgment was eternity.