Phillips, 43, was convicted in 1993 and sentenced to death for raping and murdering Sheila Marie Evans, his girlfriend’s 3-year-old daughter, according to court documents and records that describe Phillips brutally assaulting the young child again and again.

He had appealed to the U.S. Supreme Court for a last-ditch stay, questioning the state’s planned method of execution and arguing that he “bears no resemblance to that teenager” sentenced to death decades ago.

Late Tuesday, the Supreme Court denied his requests to stay the execution. The justices did not offer any explanation, though two said they felt Phillips should have had a chance to further question Ohio’s execution method.

An undated photo of Ronald Phillips. (Ohio Department of Rehabilitation and Correction via AP)

Phillips’s execution marks a rare lethal injection with significance resonating beyond the Buckeye State. Executions in the United States are increasingly unusual, as infrequent as they have been in decades and confined to a small handful of states. In part, this is because numerous states are no longer in the business of capital punishment, banning the practice outright or effectively halting it. Other states, like Ohio, have sought to carry out executions, but have been repeatedly delayed by an ongoing shortage of execution drugs along with court-ordered stays.

If that changes in Ohio, it could lead to a small uptick in executions nationwide this year. There still will be fewer executions in 2017 than in most years dating back to the early 1990s, but Ohio already has made plans for additional executions, including three set for later this year and 23 more scheduled to take place between 2018 and 2020.

Given a nationwide decline in executions, the planned Ohio executions, should most or all of them occur, could account for an outsize share of the country’s lethal injections in the coming years.

Ohio has 139 inmates on death row, among the largest such populations nationwide. For most of this young century, it also has been among the country’s most-active executioners: Between 2001 and 2014, Ohio executed at least one inmate each year, a rate matched only by Texas and Oklahoma during that span, according to the Washington-based Death Penalty Information Center.

In January 2014, unable to obtain its preferred drug for an upcoming lethal injection, Ohio turned to a new two-drug protocol, pairing midazolam and hydromorphone. The two drugs, which had never before been combined to carry out an execution in the United States, were used to execute Dennis McGuire, who had admitted to raping and murdering Joy Stewart, a pregnant newlywed, in 1989. (Officials had originally intended to first use the new combination on Phillips two months earlier, but his lethal injection was postponed.)

According to witness accounts, McGuire appeared to gasp several times during the execution and, at multiple points, made loud snorting sounds. It took McGuire 26 minutes to die, the Columbus Dispatch reported. One witness later wrote of McGuire’s death: “I came out of that room feeling that I had witnessed something ghastly.”

The Ohio Department of Rehabilitation and Correction issued a report pushing back on accounts of McGuire’s execution, concluding that the drugs “had their intended effect and that McGuire did not experience any pain or distress.” The agency also said it had decided to keep using the drug pairing but to ramp up the doses going forward.

Several months later, Ohio reversed course, stating in January 2015 that it would switch to a different drug combination, which meant rescheduling executions. The first inmate with a scheduled lethal injection postponed at that point was Phillips, who had been set to die about a month later. Not long after the January announcement, Ohio said it would postpone even more executions because it needed time to obtain new lethal injection drugs.

Ohio’s delays occurred while midazolam, one of the drugs used in McGuire’s execution (as well as in the Oklahoma and Arizona executions that same year), became increasingly controversial for its use in lethal injections. The sedative also cropped up in executions that prompted questions in Alabama last year and, earlier this year, Arkansas.

Much like Ohio, Arkansas was resuming executions after a years-long lull, hurrying to schedule an unprecedented eight lethal injections in 11 days. Authorities said the schedule was needed because their lethal drugs were about to expire and they were not sure they could obtain more. Ultimately, four of the eight executions in Arkansas were halted and the other four carried out; witnesses said the inmate lurched and convulsed during the final execution in that series.

Ohio, meanwhile, has been slowly moving toward resuming executions. Last fall, state officials announced another lethal injection combination, declaring that they would utilize midazolam along with rocuronium bromide and potassium chloride for Phillips’s execution and two others to follow, according to court records. While Phillips and other inmates challenged the new protocol, a federal judge stayed the executions, postponing them yet again, but a divided federal appeals court last month reversed that stay.

“Ohio intends to fulfill its statutory obligation of carrying out court-ordered executions in a lawful, humane and dignified manner,” JoEllen Smith, the spokeswoman for the Ohio Department of Rehabilitation and Correction, wrote in an email Tuesday.

Phillips’s brother witnessed the execution Wednesday, as did the aunt, uncle and half-sister of his victim, according to the Columbus Dispatch.

Phillips had petitioned to the U.S. Supreme Court in an effort to stay his execution. In one filing, he questioned Ohio’s lethal injection protocol, and in another argued that he should not be executed for a crime committed while he was a teenager. His attorneys also said he has changed since being convicted and sentenced.

“He has grown to be thoughtful, remorseful, generous, and reflective,” they wrote in a filing this week. In response, state officials dismissed his argument and urged the justices not to call off the execution.

The Supreme Court denied his stay requests in orders released late Tuesday, offering no further explanation. Justice Sonia Sotomayor, joined by Justice Ruth Bader Ginsburg, dissented from one order and said Phillips and other inmates should have gotten a chance to pursue their claim that “Ohio’s execution protocol is a cruel and unusual punishment.”

Attorneys for Phillips extended condolences to Evans’s family as well as Phillips’s relatives on Wednesday, echoing the arguments made in court filings that the inmate put to death was a different person.

“Ron Phillips committed an unspeakable crime when he was 19 years old, and was himself the product of a home filled with abuse and neglect,” Timothy F. Sweeney and Lisa M. Lagos, the attorneys, said in a joint statement. “But the grown man who woke up this morning at age 43, ready to face his punishment, did not in any way resemble that troubled and broken teen. He had grown to be a good man, who was thoughtful, caring, compassionate, remorseful, and reflective. He tried every day to atone for his shameful role in Sheila’s death.”

Evans’s half-sister addressed reporters at the prison after the execution:

Anti-death penalty groups called for the lethal injection to be halted, but state authorities had already denied Phillips’s earlier requests to avoid execution. The Ohio Parole Board rejected Phillips’s clemency request last year, and Gov. John R. Kasich (R) said he backed that decision.

“Given the extremely brutal nature of the offense committed against an innocent three-year-old child, I agree with the Ohio Parole Board’s recommendation that clemency is not warranted in this case,” Kasich said in a statement.

This story, first posted at 6 a.m., has been updated with details from the execution.