Two austere ostriches, Osgood and Osbad, who lived near an old gum tree somewhere in the Australian outback, ran a successful business buying cattle prods made by Cow Poke, Inc., located in Kankakee, Illinois, and selling them to cattle farmers in Australia. One day they received an order from the kookaburra who lived in their old gum tree for one of their cattle prods. He even offered cash in advance and said that he would have many other orders in the future.
Osgood looked quizically at the kookaburra and wondered why a kookaburra might need a cattle prod, but decided not to ask. As it was an unusually warm afternoon, he decided to cool off by burying his head in the sand.
Osbad, dreaming of future orders and hoping to buy a bus trip to Perth for a holiday weekend, asked the kookaburra to hand over the money and promised to bring him a cattle prod right after he paid the money, which he did.
“Don’t you wonder,” said the kookaburra, “what on earth I could possibly do with a cattle prod?”
“No!” said Osbad, “I DO NOT!! It’s quite hot and I think I’ll join my mate Osgood and cool off by burying my head in the sand.”
“Actually,” said the kookaburra, “I’m selling them to my customers in Iran,” but by the time he had said the word “Iran,” Osbad’s head was completely covered with sand and he couldn’t hear a word that the kookaburra was saying.
When the Cow Poke Cattle Prods were discovered in Iran, investigators for the Bureau of Industry and Security (“BIS”) traced them back to Osgood and Osbad. The Australians served a provisional arrest warrant on the two ostriches who were subsequently extradited to the United States for trial. Once the jurors heard that Osgood and Osbad buried their heads in the sand, it was all over for poor birds, and they were convicted and sentenced to 6 years in a maximum security prison.
On appeal to the Seventh Circuit, Judge Posner upheld the conviction of Osbad and reversed the conviction of Osgood. He noted
There is no evidence that suspecting he might be [helping the kookaburra sell cattle prods to Iran, Osgood] took active steps to avoid having his suspicions confirmed. Suppose [the kookaburra] had said to him “let me tell you [where the cattle prods are really going],†and he had replied: “I don’t want to know.†That would be ostrich behavior (mythical ostrich behavior—ostriches do not bury their heads in the sand when frightened; if they did, they would asphyxiate themselves). An ostrich instruction should not be given unless there is evidence that the defendant engaged in behavior that could reasonably be interpreted as having been intended to shield him from confirmation of his suspicion that he was involved in criminal activity. [This is exactly what Osbad did, which is why we reverse for Osgood and uphold the conviction for Osbad.]
Osbad remained in maximum security prison, while Osgood was allowed to return to the outback in Australia. On his return, Osgood found a letter from BIS indicating that it had entered a thirty-year export denial order and fined him $250,000 for the sale of the cattle prods to Iran, noting that while ignoring red flags, without more, might save you from jail, it would not save you from the wrath of BIS.
Morale: If you’re going to bury your head in the sand, do it before the kookaburra sings.
The Seventh Circuit opinion in United States v. Macias, which I adapted here, makes clear that simply ignoring red flags is not enough to support the criminal intent necessary for  a conviction. The failure to engage in further due diligence in the face of red flags is not, in Judge Posner’s view, sufficient. Instead, there must be some “active avoidance” of learning the facts that the red flags suggest may be probable.  Another example of active avoidance given in the opinion involves a hypothetical situation where a landlord, fearing he has rented his property to drug dealers, changes his normal commuting route to avoid driving by the house, fearing he might see drug activity if he did.  The “active” in the “avoidance” here is changing the route.
A fuller and more serious discussion of United States v. Macias, written by my colleague Mark Srere and me, can be found here.
[Apologies to James Thurber.]