Officials lowered a curtain to shield his body from onlookers as he was examined. They pronounced him dead 11 minutes later, at 12:15 a.m.
Among the witnesses were relatives of Gilbert Lambertson, 80, and his wife, Clara Lambertson, 73, the couple whom Bailey was convicted of killing in 1979 in their rural Kent County farmhouse.
The gallows area in the prison yard at the Delaware Correctional Center was surrounded by prison guards with shotguns and police dogs during the hanging.
``I thought this hanging would be shocking,'' said Richard Savin of the Gazette Newsmag of Wilmington. ``But it wasn't really because it happened so quick.''
Bailey, 49, went to the gallows after a meal of steak, baked potato, peas and vanilla ice cream.
Other witnesses included Bailey's attorney, Edmund D. Lyons Jr.; Saxton and Delbert Lambertson, sons of the victims; seven reporters; and several present and former police officers, including Thomas W. Robbins Sr., the state trooper, now retired, who arrested Bailey.
When the state abandoned hangings in favor of lethal injection in 1986, Bailey and two others facing death sentences were given the option of the new method. Bailey declined, saying he found the choice ``barbaric.''
Bailey's decision forced Delaware corrections officials to relearn the hangman's macabre craft from officials in Washington state - the only other state to perform a hanging in the last 30 years - and a 1969 U.S. Army manual.
For Bailey, who weighs 200 pounds, the manual recommends a drop of 5 feet 4 inches. Lyons said his client's stocky build and bull neck raised the possibility that prison officials might botch the job.
Done properly, hanging is supposed to kill quickly by slicing the spinal cord. A miscalculation can result in either decapitation or an agonizingly long death by suffocation.
Since the U.S. Supreme Court reinstated the death penalty in 1976, most states have adopted lethal injection as their preferred method. Besides Delaware and Washington state, only Montana and New Hampshire still have hanging as an option.
Bailey's method of execution made him a cause celebre for Amnesty International and generated news coverage as far away as Britain and Germany.
As the state prepared to hang him last night, about 60 death penalty opponents held a candlelight vigil in an icy wind outside the Delaware Correctional Center while a state police helicopter patrolled overhead. Bailey became the first person hanged in Delaware in 50 years.
Sally Milbury-Steen, co-president of the Delaware Citizens Opposed to the Death Penalty, said her group had attracted more supporters with each of the state's six executions since 1992.
``This one in particular has people disoriented and unsettled, so the level of discomfort rises. It compels them to take a stand,'' she said outside the prison last night.
Bailey's fate generated little sympathy among the relatives of his victims, or from 20 people who demonstrated in support of the death penalty.
Bill Lambertson, 42, a grandson of the victims who was among the death penalty supporters keeping vigil, said that hanging was an appropriate punishment ``when there's no question of doubt. They caught him . . . guns in his hand.''
On that day in 1979, Bailey fled a work-release program in Wilmington after learning that a prosecutor intended to have him classified as a ``habitual criminal'' - a designation carrying a life term - on a forged check charge.
After telling his foster sister he would kill himself before returning to prison, a crying and drunken Bailey held up a liquor store, where he tried to shoot a clerk. His gun, a .25-caliber pistol, jammed.
Next, Bailey went to the Lambertsons' nearby farmhouse, where police said he intended to steal a truck.
Instead, Bailey ran away after shooting the couple to death with the pistol and Lambertsons' single-barrel shotgun.
Saxton Lambertson is angry it took so long for Bailey to receive his punishment.
``He was caught 300 feet from the house with both guns. There was no question of guilt,'' Lambertson said.
Delaware's first recorded hanging was in 1662.
Bailey's may be the last. William Flamer, who is scheduled to die Jan. 30, chose injection; the other convict given an option, James Riley, will not make his choice until he has been given an execution date.
At a three-hour hearing Friday before the Delaware Board of Pardons, Bailey's sister and foster sister begged that his death sentence be commuted to life, citing his history of physical abuse as a child. One of 23 children of a poor family, Bailey had lost both parents by age 10 and lived in a series of institutions starting at age 12.
The board rejected Bailey's request. Friday night, Lyons learned that the U.S. Supreme Court, his last hope, had rejected his request for a hearing.
Lyons informed Bailey of the decision Saturday morning by phone.
``He was disappointed but overall fairly stoic,'' Lyons recalled.
When Lyons visited Bailey at the prison Monday and Tuesday, he searched for a joke to lighten the mood.
``Bill's a smoker and chain-smokes, and I told him one time that smoking was bad for his health. A couple weeks ago he said, `I'll make you a deal. If they don't execute me, I'll quit smoking.'
``I said to him [Tuesday], `At least you don't have to quit smoking.' And we both laughed.''