Executions in Oklahoma and Alabama, sched­uled just hours apart on September 26, high­light issues of pro­por­tion­al sen­tenc­ing and exper­i­men­tal meth­ods of exe­cu­tion. Emmanuel Littlejohn, who was exe­cut­ed at 10:17am CT, had received a rec­om­men­da­tion of clemen­cy from Oklahoma’s Pardon and Parole Board because of con­flict­ing evi­dence about whether he or a co-defen­dant actu­al­ly killed the vic­tim. Alan Miller, sched­uled to be exe­cut­ed in the evening of September 26, sur­vived a botched lethal injec­tion exe­cu­tion in 2022 and would be the sec­ond per­son in U.S. his­to­ry killed by nitrogen hypoxia.

Mr. Littlejohn (pic­tured) was the fourth per­son exe­cut­ed in Oklahoma in 2024. He was con­vict­ed and sen­tenced to death for his involve­ment in the rob­bery and mur­der of a con­ve­nience store clerk in 1992, but there is doubt about who pulled the trig­ger. During a 1993 tri­al, pros­e­cu­tors argued that Mr. Littlejohn’s code­fen­dant, Glenn Bethany, was respon­si­ble for killing Kenneth Meers, and he was sen­tenced to life in prison with­out the pos­si­bil­i­ty of parole. In Mr. Littlejohn’s 1994 tri­al, pros­e­cu­tors argued the oppo­site, insist­ing that Mr. Littlejohn was the shoot­er, not Mr. Bethany. The jury, which was unaware of the sen­tence hand­ed down to Mr. Bethany a year ear­li­er, sen­tenced Mr. Littlejohn to death, which was lat­er over­turned on appeal because of improp­er tes­ti­mo­ny from a jail­house wit­ness. He was resen­tenced to death in 2000.

During Mr. Littlejohn’s clemen­cy hear­ing, Assistant Federal Public Defender Callie Heller ques­tioned is it jus­tice for a man to be exe­cut­ed for an act that pros­e­cu­tors argued anoth­er man com­mit­ted when evi­dence of guilt is incon­clu­sive?” At the hear­ing, Mr. Littlejohn admit­ted to his pres­ence at the crime scene, but insist­ed he did not kill Mr. Meers. His clemen­cy peti­tion high­lights sev­er­al ways in which his death sen­tence is the oppo­site of reli­able” and indi­cat­ed that Mr. Littlejohn pos­es no threat to the prison com­mu­ni­ty” because of his good behav­ior, con­nec­tion to his fam­i­ly, and debil­i­tat­ing health issues” from a recent stroke and diag­no­sis of pro­gres­sive white mat­ter dis­ease.” The clemen­cy peti­tion states that if giv­en the chance to live out his remain­ing years in prison, Manuel will con­tin­ue to pro­vide famil­ial sup­port, mod­el good behav­ior, and live with remorse.”

Without issu­ing a pub­lic state­ment, Governor Kevin Stitt denied clemen­cy for Mr. Littlejohn just min­utes ahead of his exe­cu­tion. In a phone con­ver­sa­tion with NPR’s Chiara Eisner, ahead of his clemen­cy denial, Mr. Littlejohn urged Gov. Stitt to not kill [him] for the heck of it.” He told Ms. Eisner that he was scared. I have nev­er been so scared in my life. To have some­body have your life in their hands and you can’t do noth­ing about it, it mess­es with a per­son. It mess­es with them and you are going to take it up to the last sec­ond, but I will respect your deci­sion either way,” Mr. Littlejohn said. He added, I want to live and I don’t believe I deserve to die for this.”

The state of Alabama is sched­uled to exe­cute Alan Miller by nitro­gen hypox­ia — just the sec­ond time the state will attempt this method of exe­cu­tion. In September 2022, Alabama attempt­ed to exe­cute Mr. Miller by lethal injec­tion, but failed to do so when per­son­nel could not estab­lish IV lines for the lethal drugs. This exe­cu­tion attempt was one of three botched exe­cu­tions in Alabama that year. Mr. Miller was con­vict­ed in 2000 for a work­place shoot­ing that left three indi­vid­u­als dead. At tri­al, Mr. Miller’s defense pre­sent­ed a foren­sic psy­chi­a­trist who diag­nosed him with a delu­sion­al dis­or­der, which caused him to believe that the vic­tims were spread­ing rumors about him. Despite this diag­no­sis, the foren­sic psy­chi­a­trist deter­mined that Mr. Miller’s men­tal ill­ness did not meet Alabama’s stan­dards for an insan­i­ty defense. Jurors took just 20 min­utes for delib­er­a­tion and vot­ed in favor of Mr. Miller receiv­ing a death sentence.

Following his failed lethal injec­tion exe­cu­tion, Mr. Miller and the state of Alabama reached an agree­ment that any oth­er exe­cu­tion attempt would be by nitro­gen hypox­ia. In a fed­er­al law­suit, Mr. Miller claimed that the state’s cur­rent nitro­gen hypox­ia could cause him undue harm and suf­fer­ing, vio­lat­ing the Eighth Amendment pro­tec­tion against cru­el and unusu­al pun­ish­ment. Parties reached a con­fi­den­tial agree­ment, but Attorney General Steve Marshall tout­ed that this res­o­lu­tion proves the sound­ness of the method. The res­o­lu­tion of this case con­firms that Alabama’s nitro­gen hypox­ia sys­tem is reli­able and humane,” Mr. Marshall said in a statement.

If Mr. Miller is exe­cut­ed, he will be the 1600th per­son exe­cut­ed in the United States since the resump­tion of cap­i­tal pun­ish­ment in 1976.