In December of 2008, Tribune Media Services, my syndicate at the time, commissioned me to draw an illustration featuring Barack Obama and several of our other presidents, for a special Inaugural Edition to be published by The Chicago Tribune.

Recently, I’ve been asked why there are two versions of this illustration? The one posted to the right was the original illustration. Tribune Media’s managing editor and I had agreed on the concept, and the final rough draft had been approved. When I sent the finished art, as an e-mail attachment, it, too, was approved.

And so the story might have ended. But, a couple of days later, the managing editor called me to say there was a problem. Tribune Media’s president did not like the fact that there was a pair of shoes speeding in the direction of outgoing president George W. Bush’s head. This little joke, in what was otherwise a rather sober illustration, was playing homage to the famous “shoes-heard-’round-the-world” last autumn, when an Iraqi journalist hurled his shoes at President Bush during a news conference in Baghdad with Prime Minister Nuri al-Maliki. Assorted videos of the shoe assault, from every imaginable angle, were broadcast the world over, for weeks.

(As an aside, I have to admit that I was much impressed with President Bush’s nimbleness in ducking the leather projectiles. At age 62, the president didn’t miss a beat, and took it all in good humor. Meanwhile, al-Maliki was equally impressive, being absolutely unflappable as the shoes sailed between himself and the president. Of course, al-Maliki is a man who doesn’t sweat the small stuff. During some previous press conferences, the Iraqi prime minister delivered his opening remarks, or took questions, while bullets flew or bombs detonated in an adjoining room. He’d stand there passively, hardly so much as blinking, while ministerial aides and journalists dove for cover).

But back to the point of today’s blog. Tribune Media’s president told the managing editor that the shoes had to go! The president’s concern was that the dig at Bush might scare off advertisers from peddling their wares, for hefty fees, in the Obama Inaugural Edition. This was especially important, given that The Chicago Tribune is Obama’s “hometown” newspaper. Not to mention that the Tribune had recently filed for Chapter 11 bankruptcy.

So, what to do? I balked a bit at having to make the change, though complaining is something I rarely do when working on freelance jobs. I thought his concern about the flying shoes was silly, but I knew I’d have to give in. I suggested to the managing editor that I could substitute another president for the shoes, but wasn’t sure which president to choose. The managing editor said she’d leave that up to me, but hoped I’d be able to make the correction in a couple of days.

Given George W. Bush’s placement in the foreground of the illustration, I knew I’d have to choose a short president, and preferably hefty one, to fill the gap. That ruled out William Howard Taft, of course, who was 6-feet-tall and weight over 300 pounds. It also ruled out James Madison. Our shortest president, Madison was also the teeniest — just over 5-feet, and weighing barely 100 pounds. Many other presidents, regardless of size, just weren’t “household faces,” and might have puzzled readers.

John Adams, therefore, was the obvious choice. Because I draw at a drafting table, rather than on a computer tablet, I was going to have to trace part of the original art, and carefully construct a patch, with both John Adams and a re-drawn George W. Bush. Once completed, I could literally glue the patch into place, or scan the patch and “paste” it onto the JPEG image of the original art. I opted for the latter, so as to preserve the original piece with the hurtling shoes. Or, rather, I would opt for asking my wife to handle the digital surgery for me. She’s an expert with Photoshop. I’m basically a digital idiot.

Once the patch was inserted, I sent the revised file to Tribune Media Services. Everyone there breathed a sigh of relief. A funny thing happened, though, on the way to the printer. The special Obama Inaugural Edition was full of large editorial cartoons by some of Tribune Media’s best cartoonists. And my own illustration was given good play, as well. The only thing is, the special edition contained NO ADVERTISING WHATSOEVER! Even without the flying shoes, Tribune Media was unable to enlist a single advertiser for the suppliment. The shoe crisis was really much ado about nothing. It was also another example, however small, of the sad shape of today’s newspaper industry.

Still, I can’t complain. My illustration took up half a page of the special edition in Barack Obama’s hometown newspaper. No clunky advertisements were there on the page to compete with my art (an ad for shoes would have been wonderfully ironic). And, in my opinion, the revised illustration makes for a better composition. Also, my revision of Bush, I believe, was better than the first version. Curiously, I’ve always found George W. Bush a struggle to caricature well. Comparatively, Barack Obama’s face is a breeze to draw.

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