60-year old John Jacques of Wisconsin owned, in some kind of unintentional effort to reinforce every stereotype of pedophiles, a van. That van advertised "Jacques Computer Services," and Jacques billed himself as a Web developer and a programmer—though, if he really knew the Internet as well as he claimed, he would've realized that 13-year-old girls using Yahoo Instant Messenger and sending him blushing emoticons when he offered them dirty pictures were probably not 13-year-old girls.

And, of course, they were not. "Annie" and "Ashliee" were the online aliases of a local Wisconsin detective who hung in what the court calls "romance" chat rooms, where Jacques made contact with both of them. Over the next two months, he chatted with the two "girls," escalated the sexual nature of the chats until they involved various webcam activities unbecoming to either 60-year-old men or 13-year-old girls. Eventually, he asked "Annie" to meet in real life and then to spend the night at his apartment. She agreed. When Jacques showed up for the meetings, cops arrested him.

Jacques was convicted in 2008, but his case then took a curious turn. Working as his own lawyer, Jacques filed an appeal of the verdict on the grounds that he had been "entrapped" by the various animated emoticons "Annie" and "Ashliee" had used in their replies to him.

These emoticons, which included a blushing face whenever the discussions turned towards sex, did not appear in their fully animated glory at Jacques' trial. Instead, his LaCrosse County Court jury saw only printed transcripts of his instant messaging chats (his username: "jackjacq") in which the blushing faces were mere static images. The full effect of that animated blush, it was alleged, led Jacques down the broad way that leads to destruction, a way he would not have walked on his own.

As the state of Wisconsin pointed out (PDF) while arguing the appeal, law enforcement officials are allowed to engage in “some inducement, encouragement, or solicitation in order to detect criminals.” But courts have previously ruled that this crosses the line into impermissible “entrapment” when the officer uses “excessive incitement, urging, persuasion, or temptation, and prior to the inducement, the defendant was not already disposed to commit the crime."

Blushing emoticons, in the state's view, did not excessively incite Jacques to hang out in "romance" chat rooms, contact the girls, masturbate in front of his own webcam, send nude pictures, or invite someone he believed to be 13 to spend the night at his apartment.

"In short," the state concluded, "Jacques' 'emoticons made me do it' theory of exoneration lacks any support."

The state Court of Appeals concurred. In a terse opinion (PDF) last week, the court concluded, “Our confidence in the outcome is not undermined because the jury did not view animated emotions.”

Jacques will continue to serve his 15-year prison sentence in a LaCrosse jail.