What makes Chapman's case groundbreaking, lawyers say, is his decision to waive trial and sentencing by a jury, and then nearly beg to be sentenced to death. Professors who teach criminal law have found Chapman's case - and its potential implications for future defendants - disturbing.
His own lawyers say Chapman is trying to use the legal system to commit "suicide by court."
On Thursday, the Kentucky Supreme Court is set to hear arguments on the legality of Chapman's request, part of the automatic appeals process in all death penalty cases.
The case has the unusual twist of putting prosecutors and Chapman on the same side arguing for the death sentence while Chapman's court-appointed defense attorneys seek to stop the lethal injection.
"This is a defense lawyer's worst nightmare," said Michael Mello, a University of Vermont law professor and former lawyer for death row inmates in Florida.
Chapman, who has turned down multiple interview requests, pleaded guilty in December 2004 to killing 7-year-old Chelbi Sharon and 6-year-old Cody Sharon in their home in the northern Kentucky community of Warsaw. Chapman also admitted stabbing 10-year-old Courtney Sharon, who survived, then raping and trying to kill their mother, Carolyn Marksberry, during the 2002 assault. A judge granted his request to be sentenced to death.
The Associated Press does not name victims of sexual assault in most cases, but Marksberry has discussed her ordeal in local and national television broadcasts.
Nationally, volunteering for a death sentence is not new. Since 1977, when Gary Mark Gilmore waived his appeals and stepped before a firing squad in Utah, 124 inmates in 26 of the 38 states with a death penalty law have waived appeals and asked to die, according to the Death Penalty Information Center in Washington. Texas, with 26 people volunteering, leads the nation in inmates giving up the fight against a death sentence.
One of the two people executed in Kentucky since 1976 waived the remainder of his appeals and was executed in 1999.
Michael Hoffheimer, a criminal law professor at the University of Mississippi, said a ruling giving deference to a convicted man's decision to seek a death sentence could be troubling because it would take away multiple legal safeguards to ensure that only a competent, guilty person is put to death. Without those safeguards, there's a chance someone who is not guilty, but suicidal, could be executed, Hoffheimer said.
"Permitting defendants to make decisions that increase the risk of wrongful convictions is bad policy," Hoffheimer said.
Cornell University law professor John Blume, who wrote an analysis of death penalty volunteers for the University of Michigan Law Review, said attorneys have no obligation to aid a client in dropping appeals. However, he said a court must make sure there are no questions about guilt and competence, and that "the desire to drop the appeals is not a desire to end their life but rather they are motivated by an acceptance of responsibility for their crimes."
Mello, who once represented serial killer Ted Bundy, said the decision should remain that of the man on death row, provided he is competent. "The heart of the matter is, whose life is it?" Mello said.
Chapman's court-appointed attorneys, Donna Boyce and Randall Wheeler, and Vicki Glass, a spokeswoman for the Kentucky Attorney General's Office, have all declined to comment.
In briefs with the high court, Boyce and Wheeler argue that the trial judge mishandled the case and that Chapman was depressed and seeking to use court proceedings to commit suicide. They want a new sentencing hearing after Chapman has been treated for depression.