During his first US visit in 1979, JP II gave an outdoor Mass at Grant Park in Chicago. I was a senior at Notre Dame at the time, and I covered the Mass for the student radio station.
It was almost 2 years before the assassination attempt, so security wasn't that tight. There were no screenings even though he walked just past the press area on his way to the altar. Things changed considerably when I saw his motorcade pass in Miami in 1987. Security was much tighter by that time.
His homily in Grant Park was doctinarily extremely conservative. He repeatedly used the term "E Pluribus Unum" to argue, in essence, that all Catholics must rally around the papal flag. That homily set the tone for his approach on matters of Church discipline over the course of his papacy.
This pope had so many good things to say on so many subjects--the war in Iraq, the death penalty, and Third World debt relief being the most classic examples. Unfortunately, his insistence on hierarchical supremacy often tended to, in the final analysis, undercut those views. Unlike Paul VI, who made a remarkable series of episcopal appointments in the US, JP II tended to promote obedient careerists here.
Many American bishops tacitly supported W in 2004, and some of them (e.g St. Louis and Denver--both in swing states) weren't the least bit tacit about their views. The Catholic vote went 52-47 for Gore in 2000, it went for W by the opposite margin in 2004. That swing was, arguably, decisive.
In other words, the American hierarchy, all of which was appointed by JP II, helped a president who promoted a war that violates fundamental Church teachings obtain a second term. Along the way, they generally dissed the only Catholic to obtain a major party nomination in the last 44 years. Regardless of what one thinks on the difficult topic of abortion, the Church's treatment of Kerry last year was inexcusable.
The true tragedy of JP II was that he often took actions that undercut his words. I feel a senses of sadness at his death, but I also feel a sense of regret that things couldn't have turned out differently.