Credit: Greg Houston

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With slim hope of overturning his 25-year prison sentence, Keith Antoine Jackson offered a Hail Mary all-or-nothing appeal that hinged on one issue: his tattoo.

In his recent case before the D.C. Court of Appeals, Jackson argued that he should have been allowed to use makeup during his murder trial to conceal his tattoo, a teardrop etched in black ink below his eye.

Jackson claimed his constitutional right to be presumed innocent at trial was undermined because a teardrop tattoo can signify that the wearer has killed someone. In a masterful use of a double negative, his court-appointed attorney argued that the tattoo’s prejudicial impact on the jury “cannot be said to have not contributed to the manslaughter guilty verdict,” an appeal brief states.

Jackson was a 17-year-old, unemployed, high-school dropout in 2002 when he opened fire with an assault rifle, killing a man outside a Southeast apartment complex in a feud over a $50 debt for some used tires, court records state. After being tried as an adult, he was convicted for manslaughter and several firearms offenses, leading to his 25-year sentence and his appeal.

The D.C. Court of Appeals isn’t known for racy opinions. Judges tend to write dry dissertations on fine points of the law, so the April 3 decision in Jackson’s case was definitely unusual. It may be the first time the court has debated the West Coast gang origins and alternative meanings for a teardrop tattoo.

“We have no trouble agreeing with Jackson that the teardrop tattoo had at least some potential to portray Jackson—in the eyes of any jurors who might have been aware of what defense counsel characterized as the tattoo’s ‘West Coast’ meaning—as an individual who had killed before,” the unanimous decision states.

But the panel of three judges didn’t agree with much else. It was a downhill trip for Jackson, in part because the teardrop tattoo has strayed from its gang roots and is open to new meanings. Even Amy Winehouse, the pasty-white British singer and frequent rehab patient, sported a teardrop tattoo last year after her husband went to prison.

At a hearing before Jackson’s trial in 2004, public defender Anthony Matthews asked D.C. Superior Court Judge John Bayly Jr. to let Jackson conceal his teardrop tattoo during his trial because of the tattoo’s original meaning. “In some circles, the presence of a teardrop tattoo means that the person wearing it has killed somebody,” Matthews said at the hearing. “That is sort of gang understanding from the West Coast, and many people in the [D.C.] community are aware of that interpretation.”

But Matthews acknowledged that people often get teardrop tattoos to mourn the loss of a loved one. Other reasons for a teardrop include a long stint in prison by the wearer or a loved one. The tattoo’s meaning also can shift if the tear is empty or filled with ink.

Bayly shot down Jackson’s makeover request after a prosecutor said a witness might need to identify Jackson by his tattoo. At his trial, Jackson offered his own reason for getting inked, which was the innocent version.

“I got it for the loss of my dead relative that was close to me,” he testified. “I got it resembling shedding a tear for them, that I miss them.”

The D.C. Court of Appeals found the tattoo didn’t affect the guilty verdict, so the court affirmed all of Jackson’s convictions. “If the jury viewed Jackson as violent or aggressive, there is no reason to believe that this belief was caused (or bolstered in any significant way) by seeing and interpreting his tattoo, rather than by hearing the evidence of his ownership of an assault rifle and the evidence about the violence of the May 1, 2002 incident itself,” the decision states.

That night began without any signs of trouble at the Rockburne Estates apartment complex in Southeast. Jackson and a group of men were drinking screwdrivers from plastic cups when Jackson agreed to sell a set of used tires for $100 to Lorenzo “Lo” Benning, court records state.

Benning paid $50 for the tires and promised to pay the remaining $50 later, which prompted an argument between Jackson and 24-year-old Clinton “Black” Hodges, Benning’s friend, who was helping change the tires on Benning’s Chevrolet Caprice. Jackson walked away, but he delivered a dire warning, according to court records.

“I will get my gun and shoot you,” Jackson said. “I will be back. It’s not a game.”

A short time later, Jackson returned, swinging a Type 56 assault rifle, a Chinese knockoff of the Russian AK-47 assault rifle and an uncommon sight on the streets in D.C., where handguns predominate.

As Jackson approached the group working on the Caprice, several men scattered. Jackson leveled the assault rifle and began firing, according to witness statements. Two bullets ripped through Hodges’ back, while another slammed into his head from close range.

As he pulled the trigger, Jackson said, “What’s up now, Black?” or “How do you like me now, Black?” court records state.

Jackson offered a very different version of events. He testified that he shot Hodges in self-defense “out of fear and shock” because Hodges had threatened him and swung a tire wrench. Jackson testified that he ran away after the killing “because I just shot someone and I never shot anyone.”

Even though Jackson’s self-defense claim was contradicted by witness testimony and other evidence, it was enough to convince the jury to acquit him of first-degree murder, second-degree murder, and several other charges. But he was convicted for manslaughter and firearms charges related to the assault rifle.

Sydney Hoffmann, a private attorney appointed by the court to represent Jackson on appeal, says she has no reason to doubt Jackson’s stated reason for getting the tattoo, but she says he may have just wanted to look tougher on the street. Jackson had no adult criminal record before the killing, and his juvenile record was limited to one minor charge, she says.

“He was not someone who was on the radar screen as far as criminality at all,” she says.

Teardrop tattoos have spilled over in court cases in other jurisdictions. James Lee Henderson, a Crips gang member, was sentenced to death for the 1993 murder of an 85-year-old woman during a break-in in Palestine, Texas. Henderson got inked with a teardrop tattoo in the county jail in Dallas after the killing, which resulted in the tattoo being used as evidence at his trial, where he was forced to step up to the jury so they could see the permanent tear below his left eye. Henderson is still on death row after several unsuccessful appeals.

In another Texas death-row case, Michael Dean Gonzales argued that a police detective shouldn’t have been allowed to testify that Gonzales’ two teardrop tattoos represented the number of people he had killed. Gonzales was convicted for stabbing his two neighbors to death, and a federal court rejected his appeal in 2006, stating there was so much evidence against him that the tattoo testimony didn’t really matter.

As for Jackson, he is incarcerated in a medium-security prison in New Jersey. His projected release date is in 2024, when he will be 40.