On Sept. 5, 1989, US president George H.W. Bush made a televised speech from the Oval Office announcing his administration’s escalation of the so-called “War on Drugs.” To illustrate the gravity of situation, Bush held up a bag of crack cocaine on live TV—drugs purchased, he told viewers, just steps from the White House where he now sat.

Bush’s speechwriters hit upon the idea of the visual aid days before the speech. The only problem was reality: There weren’t many drug sales in the area immediately around the White House, as University of Baltimore assistant professor Joshua Clark Davis highlighted recently on Twitter.

To supply the locally sourced crack, agents from the Drug Enforcement Administration had to lure a dealer to a part of Washington well outside his usual territory. (When the story came out, the White House denied that they had ever asked the DEA to set up a sale.) Agents decided upon Keith Jackson, an 18-year-old high-school senior who had never ventured to Bush’s neighborhood before.

“Where the [expletive] is the White House?” he asked undercover agents in a secretly recorded conversation. Undercover agents had been talking to Jackson, a small-time dealer, in the hopes of getting information on a more powerful one. After much cajoling, Jackson met an agent in Lafayette Park just next to the White House, an area whose heavy foot traffic and police presence normally precluded any drug activity.

Jackson collapsed in tears after his conviction. He had no prior criminal record. He was later sentenced to 10 years for this first offense, a sentence reluctantly imposed by US District Judge Stanley Sporkin, who by that time was forced to work off of mandatory minimum sentencing laws passed by Congress in 1988 as part of the War on Drugs.

“[Bush] used you, in the sense of making a big drug speech,” Sporkin told Jackson during his sentencing (paywall). “But he’s a decent man, a man of great compassion. Maybe he can find a way to reduce at least some of that sentence.”

Bush never did. “The man went there and sold drugs in front of the White House, didn’t he?” Bush told reporters (paywall). “I can’t feel sorry for this fellow.”

Since his death on Nov. 30 at age 94, Bush has been praised for his many examples of gracious bipartisanship, particularly in contrast to today’s bitterly divided politics. But the darker parts of his legacy reveal ugly moments when Bush played off divisions—not between his fellow members of the privileged ruling elite, but between the largely white, middle-class voters to whom his policies were designed to appeal and the poor communities of color they targeted.

One of Bush’s most infamous legacies is the “Willie Horton” ad, deployed on TV during his 1988 presidential race against Michael Dukakis. To portray Dukakis as soft on crime, the commercial highlighted the case of Willie Horton, who raped a woman after escaping prison during a weekend furlough program that Dukakis supported. But its lingering focus on a prison photograph of Horton, a black man, was criticized for appealing to white voters’ racism.

Today, in large part due to the legacy of drug sentencing laws, the US has the world’s highest incarceration rate. Nearly 80% of people in federal prison and 60% of those in state prisons for drug offenses are black or Latino, according to the Drug Policy Alliance.

Keith Jackson is no longer one of them—he was released from prison in 1998.