Although we thought that the signature moment of George W. Bush’s presidency would have been his standing in a flight suit before the “Mission Accomplished” banner on an aircraft carrier after the initial invasion of Iraq in 2003, this episode may well have been booted to the side by the scene of the president being insultingly pelted with an Iraqi journalist’s footwear.

This embarrassing saga illustrates that the Bush presidency has trod from tragedy to farce. The president’s well-heeled upbringing has led to the “rich boy” syndrome, in which throughout Bush’s life his wealthy father bailed out this footloose and fancy-free loafer. Thus, Bush began to believe that his “bold” (read: reckless) actions would always turn out OK. Also, Bush can be labeled a “sneaker” for his post-9/11 fabrication of a link between Saddam Hussein and al Qaeda or 9/11, in order to invade a second, unrelated Muslim nation. Meanwhile, he merely temporarily shooed away Osama bin Laden—allowing a worldwide radical Islamist movement, strengthened by non-Muslim footsteps in Iraq, to possibly threaten the United States another day.

Of course, the invasion of Muslim lands by non-Muslim armies was far more insulting to the Islamic world than failing to remove your shoes when entering a mosque. Hence the ultimate symbolic rejoinder of wing tips flying through the air at the Baghdad news conference—a slight that has proved wildly popular throughout the Muslim world.

Bush has tried to spit and polish the entire Iraq affair by emphasizing that violence has been reduced to 2004 levels (which we thought were horrendous back then), but after more than five long years of war, more than four thousand American casualties, tens or even hundreds of thousands of Iraqi casualties, and the wasting of hundreds of billions of dollars, this is like trying to shine up an old, worn out sole that the dog has dragged in. And no amount of Karl Rove’s fancy footwork in the public relations realm to repair Bush’s legacy will eventually rehabilitate him as a modern day Harry Truman—especially if the other shoe drops and a massive ethno-sectarian civil war breaks out after U.S. troops hoof it out of that country.

But Iraq is not even the worst part of the Bush record. Concomitant to his “war on terror,” he trampled civil liberties by eliminating habeas corpus for terror suspects, trying them in kangaroo military tribunals, and flagrantly violating criminal statutes by torturing them and spying on Americans without warrants. Prior to Bush’s taking office, the imperial presidency had created big shoes to fill, but all of these policies swelled Bush’s ankles (along with his head) so that they easily burst the seams. Creation of a hyper-imperial presidency may be Bush’s most lasting footprint.

And what about Bush’s post-9/11 “improvements” in homeland security? If journalists are now required to remove their shoes, for security reasons, at presidential press conferences, maybe they will write more critical stories about the ridiculous removal of footwear that average airline passengers have to endure every time they fly. Frankly, such unconstitutional searches in the name of faux airport security, with no probable cause of criminal behavior, smell.

History will also remember that the federal government’s preparation and response to Hurricane Katrina required the residents of New Orleans to have hip waders—both to combat the rising flood waters and to deal with the Bush’s hogwash about Brownie doing a swell job.

In addition, the sheen of Bush’s legacy will be forever smudged by the severe economic meltdown that occurred after eight years of runaway federal expenditure that made Imelda Marcos’s spending look restrained. (Birken)stocks plummeted and a Republican brand of socialism—which would have made even the shoe-banging Nikita Khrushchev proud—gained a renewed foothold in the American economy.

Even the few times that Bush tried to do the right thing—by attempting Social Security and immigration policy reform—he either barely and unsuccessfully dipped his toe in the water or did a shabby job, respectively.

In short, Bush’s presidency has tracked mud all over the American reputation abroad and driven a stiletto (heel) into the heart of the American republic at home. As Barack Obama goes through the boot camp of the presidential transition, he needs to learn from Bush’s shoddy presidency.