Oscar Ray Bolin Jr. was executed by the State of Florida on January 7, 2016, for the murder of Teri Lynn Matthews, a 26-year-old bank worker taken from outside a post office in Land O' Lakes, north of Tampa, on the morning of December 5, 1986. He had also been convicted of killing two other women that year in Hillsborough County: Natalie Blanche Holley, 25, a restaurant manager, in January, and Stephanie Collins, 17, a high school student, in November. All three were stabbed, the Associated Press reported.
The killings went unsolved until July 1990, when the new husband of Bolin's former wife called Crime Stoppers in Indiana. By then Bolin was in prison in Ohio for kidnapping and rape. What followed in the Florida courts lasted more than 25 years. The Florida Supreme Court reversed his convictions again and again, mostly because his former wife had been allowed to repeat what he had told her in private during their marriage. Each time a new jury heard the case, it found him guilty. The AP counted ten guilty verdicts from ten juries in three cases. He married a former member of his defense team in 1996 in a wedding carried on television, and he went to his death saying he had never met the three women.
Bolin was born on January 22, 1962, according to the Florida Commission on Capital Cases, which tracked death penalty cases for the Florida Legislature. Little has been reported about his early life beyond what his lawyers presented as mitigation at his sentencing hearings. In the Collins case the trial court accepted, and gave some weight to, evidence that he had been abused as a child. It also accepted, and gave little weight to, the effects of his mother's alcoholism and of his own substance abuse, a poor and unstable childhood, and a sporadic and minimal education. He earned a high school equivalency diploma in prison and had skills in welding, electrical work, plumbing and small machinery, the court found. He was 24 in 1986 and was working at the time. Once, the court accepted, he had saved another person's life.
In the Matthews case the sentencing judge found that he had a somewhat difficult childhood and improper care as a child, some evidence of minor brain damage or mental illness, a history of several suicide attempts, and some alcohol and drug use as a minor without dependency. A defense psychologist testified in the Collins case that Bolin suffered from mental illness, including psychosis, but he could not link it to the night of the killing, and the court rejected the claim that Bolin's capacity had been substantially impaired.
Patch, the local news site, described him as a former carnival worker and long-haul trucker. In 1986 he was married and lived in the Tampa Bay area. His wife at the time later became the most important witness against him.
Natalie Blanche Holley was 25 and worked as a manager at a fast-food restaurant in Tampa. In the early hours of January 25, 1986, she left work after closing. Her body was found later that morning, and her car was found abandoned elsewhere, the Florida Supreme Court recorded. The AP reported that she had been abducted after leaving her job.
One detail from the night stayed in a sheriff's file for years. The evening before, a deputy had run a license tag check on one of two cars parked on the same corner. The car was registered to Bolin and his wife.
Her mother went on to attend many of Bolin's trials alongside the mothers of the other two women. She died in 2012, the year of the last trial in her daughter's case, according to the AP.
Stephanie Collins was 17, a high school student in Tampa, according to Patch. On November 5, 1986, she stopped by the drugstore where she worked, and then she disappeared. That afternoon two witnesses saw her in the passenger seat of a white van with a man they could not identify, the Florida Supreme Court recorded. Patch said she was taken from a shopping plaza.
Her body was found in Hillsborough County on December 5, 1986, a month after she went missing. The medical examiner found that she had been beaten and stabbed. Her purse held a note that read "724-BYL, Ray." The numbers and letters matched the tag of Bolin's pickup truck, and Ray was the name he went by, according to the court.
After the execution her mother said the family missed Stephanie every day but would keep their fond memories of her, Bay News 9 reported.
Teri Lynn Matthews was 26. She worked nights at a bank in Tampa and had recently taken up scuba diving, taking lessons during the day, NBC News reported in 2016. She had been a high school cheerleader, and her mother remembered that she was always smiling. She had a serious new boyfriend and had just bought a mobile home, which she was fixing up so that she could move out of her parents' home in Pasco County.
On the morning of December 5, 1986, she did not come home from work at the usual time. Her mother assumed she was with her boyfriend until he telephoned the house looking for her. He retraced her route from the bank toward the post office in Land O' Lakes where the family kept a mailbox, and he found her car in the lot, still running, with the headlights on and her wallet on the seat. The court record says her purse was untouched in the car and her mail lay scattered on the ground nearby.
By the time her parents arrived, a sheriff had news that an unidentified young woman's body had been found in rural Pasco County. Deputies showed her mother a pair of earrings taken from the body. She recognized them: she had bought them for her daughter so that she would stop borrowing her own.
A hospital sheet found with her body, tire tracks and her car keys became evidence. She had been stabbed and beaten. Collins's body was found the same day, in neighboring Hillsborough County.
The three cases sat unsolved for more than three years. When they were reopened, almost everything began with the woman who had been Bolin's wife in 1986; she had divorced him and remarried by 1990. The Florida courts later set out her accounts in detail, though how much of them a jury could hear became the central legal question of the whole case.
In the Holley case she said she had been with Bolin when he looked over the restaurant where Holley worked, and that she fell asleep after they got home. At about 2 a.m. he woke her and told her he had abducted and killed the woman. She helped him clean Holley's car, and he got rid of his tennis shoes and Holley's purse. In a deposition played at the 2012 trial, she said he changed shoes that had blood on them, threw a purse and shoes out of the car window on a highway, and washed the car thoroughly the next day, Bay News 9 reported.
In the Collins case she said that on November 5, 1986, Bolin picked her up from a restaurant and, on the drive home, tried to explain that there was a dead body in their travel trailer. He told her he had killed a girl by hitting and stabbing her. She said she rode with him when he took the body away, and later showed police where. Back at the trailer she saw signs of a cleanup and a knife. She also supplied hospital sheets like one found with Collins's body; in the Matthews case she identified a hospital sheet resembling the one found with Teri Lynn Matthews.
The AP reported that she said Bolin had told her about the killings in 1986. She did not go to the police. She went instead, years later, to the man she had married next.
In 1987, the year after the Florida killings, Bolin kidnapped a 20-year-old woman near Toledo, Ohio, according to the AP and the Florida Supreme Court. He pleaded guilty in 1988 to kidnapping and rape. While he was held on that case he tried to escape and attacked a jail guard, and he pleaded guilty in 1988 to felonious assault and escape. The AP reported his Ohio sentence as 22 to 75 years; ABC News in 2015 gave it as 25 to 75 years. The woman he kidnapped survived.
The AP also reported that Bolin was officially linked to the 1987 strangling of Deborah Diane Stowe, 30, in Greenville, Texas. A cousin told authorities that he and Bolin abducted her outside a convenience store and that Bolin killed her. Texas prosecutors declined to seek an indictment. The killing was never tried, and no court has linked Bolin to it.
In July 1990 her new husband called a Crime Stoppers line in Fort Wayne, Indiana, with what his wife had told him about the Collins killing. Investigators from Florida interviewed her, and she implicated Bolin in the Collins and Holley cases. Through her, investigators came to Bolin's half-brother, who had been a teenager in 1986, and to the Matthews case. The AP reported that authorities learned only later that the anonymous caller was her new husband, and that defense lawyers would point out that she had received Crime Stoppers reward money.
A Hillsborough County grand jury indicted Bolin on August 1, 1990. In the Holley case the charges were first-degree murder, armed robbery and kidnapping; in the Collins case, first-degree murder, attempted robbery and kidnapping. A Pasco County grand jury indicted him for the first-degree murder of Teri Lynn Matthews on February 19, 1991. He was brought from Ohio to the Hillsborough County jail to stand trial.
On June 22, 1991, while he was awaiting trial, Bolin tried to take his own life in the jail. In his cell investigators found a stamped envelope on a cardboard box, addressed to Captain Gary Terry, the chief investigator, who had built a rapport with Bolin in earlier interviews. Terry opened it. In the letter Bolin discussed the investigation and told Terry that anything more he wanted to know he would have to ask his former wife, because she knew nearly everything he had been involved in, according to the Florida Supreme Court. At the 2012 Holley trial prosecutors read jurors a passage in which, Bay News 9 reported, he wrote that the idea to dump the body had been hers.
The letter would be argued over for the next 20 years. Prosecutors said it showed he had given up the marital privilege, the rule that lets a spouse keep private conversations from a courtroom. The defense said he had never meant to waive anything.
The Holley case was tried first. On July 11, 1991, a Hillsborough County jury found Bolin guilty of first-degree murder, armed robbery and kidnapping. The jury voted 11 to 1 to recommend death, and on July 31, 1991, Judge M. William Graybill sentenced him to death for the murder, to 30 years for armed robbery and to life for kidnapping, according to the Commission on Capital Cases.
On October 11, 1991, a second Hillsborough jury found him guilty of the first-degree murder of Stephanie Collins and of the lesser offense of false imprisonment, and acquitted him of attempted robbery. The jury recommended death 12 to 0, and he was sentenced to death.
In Pasco County, a jury found him guilty of the first-degree murder of Teri Lynn Matthews on October 12, 1992, and recommended death 12 to 0 two days later. Judge Stanley Mills sentenced him to death on October 30, 1992.
His former wife did not live to see the later trials. She died in 1992, Bay News 9 reported; because she was terminally ill, her testimony had been recorded on videotape, according to the Florida Supreme Court, and later juries watched it.
On April 21, 1994, the Florida Supreme Court threw out the Holley convictions. The trial judge had ruled that Bolin waived the marital privilege when his lawyers took his former wife's discovery deposition, and so allowed her to tell the jury what he had told her. The justices called the question one of first impression in Florida and held that merely taking a discovery deposition does not waive the privilege. Because her account of his statements had played a significant part in the state's case, the error was not harmless. The court ordered a new trial (Bolin v. State, 642 So. 2d 540).
The Collins conviction fell for the same reason. The court reversed it the same day and, after rehearing, issued a revised opinion on February 9, 1995, again ordering a new trial (650 So. 2d 21). The same day it reversed the Matthews conviction on related privilege grounds (State v. Bolin, 650 So. 2d 19). In the Collins remand the court left open whether the jail letter might itself be a waiver.
Before the Collins retrial, the trial court suppressed the letter. The Second District Court of Appeal reversed in 1997, holding that Bolin had no reasonable expectation of privacy in his cell (State v. Bolin, 693 So. 2d 583). The Florida Supreme Court declined to review that ruling, and the United States Supreme Court denied certiorari.
During the retrials Bolin's life took a turn that drew more attention than the cases themselves. Rosalie Martinez was a paralegal at the Hillsborough County Public Defender's office and worked on his defense team. She was married to a prominent Tampa lawyer. The two fell in love while Bolin was on trial, the AP reported. She told ABC News in 2015 that she had brought him depositions and asked him to mark the inconsistencies, and that long study of the record convinced her he was innocent. She dated her campaign for him to February 3, 1995.
She divorced her husband, and in 1996 she married Bolin. The AP described it as a wedding on live television. ABC's 20/20 covered it: she wore a wedding dress, a photograph stood in for the groom, and the vows were exchanged over a speakerphone, since he was on death row. NBC News reported that they were married by telephone with cameras present. She told the AP at the time: "Oscar came into my life and I thought, 'This is bigger than anything I've ever done.'" In place of a honeymoon, she told ABC, the couple were in a courtroom when he was sentenced to death in one of the cases.
Teri Lynn Matthews's mother said the wedding "made kind of a mockery of the whole thing," BuzzFeed News reported, and she later told NBC News that the attention should be on the victim.
As Rosalie Bolin she went on to work as a licensed private investigator and mitigation specialist, according to ABC News, and she became one of the most outspoken opponents of the death penalty in Florida, according to the AP. She maintained that her husband was innocent of the Matthews killing. They never lived together, she told ABC in 2015; she visited him twice a week, and he sent her letters and hand-drawn cards nearly every day.
The Matthews retrial came first. On August 21, 1996, a Pasco County jury again found Bolin guilty of first-degree murder and recommended death 12 to 0. He was resentenced to death on October 9, 1996. On June 10, 1999, the Florida Supreme Court reversed again, this time because the trial judge had refused to question jurors who had been exposed to news coverage individually and apart from the rest of the panel (Bolin v. State, 736 So. 2d 1160).
The Holley case was retried in Hillsborough County in February 1999. On February 18 the jury found him guilty on all counts and on the next day voted 11 to 1 for death. The Collins retrial ended on April 8, 1999, with guilty verdicts for first-degree murder and false imprisonment and a 12 to 0 recommendation of death. On June 4, 1999, Judge J. Rogers Padgett resentenced him to death in both cases.
In both, the trial court had found that the jail letter waived the marital privilege, and the jurors had heard his former wife's videotaped account of what he told her. On July 13, 2001, the Florida Supreme Court reversed the Collins conviction (Bolin v. State, 793 So. 2d 894). The justices found no competent, substantial evidence of a voluntary waiver. He had written the letter after a judge had already ruled that his privilege was gone, so at most he was going along with that ruling; the letter pointed the investigator toward other matters rather than releasing her earlier testimony; he had never handed it over to anyone; and his renewed objection would have revoked any waiver in any case. Her testimony about his private statements had been the central focus of the state's case, so the error was not harmless. On August 30, 2001, the court reversed the Holley convictions on the same reasoning (Bolin v. State, 796 So. 2d 511).
The court drew a line that would shape the later trials. What she had seen with her own eyes was not privileged. Only what he had told her in confidence was.
The third Matthews trial ended on October 24, 2001, with a verdict of guilty as charged. Bolin waived a jury recommendation on sentence and the presentation of mitigation, and on December 28, 2001, he was again sentenced to death. The judge found three aggravating factors, among them that Matthews had been taken from the area of the post office.
The state's evidence at that trial was summarized by the Florida Supreme Court in later opinions. His half-brother, who was 13 in 1986, testified that Bolin woke him in the night in early December 1986 and had him help move a body. A classmate of the half-brother testified that the boy took him to the area and that he saw what looked like blood on the grass. A former employer, the wife of one of Bolin's cousins and DNA experts also testified. The wife of the cousin, Courthouse News Service reported, told the jury that in 1987 Bolin had said he killed a girl in Florida while his half-brother watched. The court said a biological sample recovered from Matthews's body matched Bolin's blood.
The half-brother had recanted before the final trial and then reaffirmed his account, saying that family members had pressured him to take it back, according to Courthouse News; the AP described the same pattern of recanting and reversing. His former wife's videotaped testimony was used for the parts that were not privileged, including the hospital sheet.
The Florida Supreme Court affirmed the conviction and death sentence on February 5, 2004 (Bolin v. State, 869 So. 2d 1196), and the United States Supreme Court declined review on October 4, 2004. His motion for postconviction relief, filed in October 2005, was denied after a hearing that ran from November 2006 to November 2007. On July 1, 2010, the Florida Supreme Court affirmed, rejecting claims that his trial lawyers should have objected to the classmate's testimony and should have called his father, a witness the lawyers, and Bolin and his wife, doubted would help (Bolin v. State, 41 So. 3d 151). A federal district court in the Middle District of Florida denied his habeas corpus petition on July 1, 2013.
The third Holley trial came in 2005. On October 7 the jury found Bolin guilty of second-degree murder, a lesser offense, and on October 11, 2005, he was sentenced to life in prison. That verdict ended the death sentence in the Holley case.
It did not end the case. On March 20, 2009, the Second District Court of Appeal ordered a fourth trial, because retired Circuit Judge Barbara Fleischer had not properly instructed the jury on a lesser included offense (Bolin v. State, 8 So. 3d 428), the Times reported.
The fourth Holley trial opened in Tampa in April 2012, 26 years after her death. Jurors again watched the deposition of his former wife, who had been dead for 20 years. The defense pointed out that she had been legally blind. One of Bolin's cousins testified that Bolin confessed to him, quoting him as saying, "I did that girl," Bay News 9 reported. The jury found him guilty of second-degree murder, and he was again sentenced to life.
The third Collins trial was heard by Judge Barbara Fleischer. The Florida Supreme Court's 2013 opinion dates the guilty verdict for first-degree murder to November 2, 2006, and says Bolin waived a penalty-phase jury. The Commission on Capital Cases recorded the verdict as November 30, 2007, with a 12 to 0 jury recommendation of death, and a death sentence on December 5, 2007; the Times reported in 2009 that he received his third death sentence for Collins in December 2007.
The evidence at that trial went beyond his former wife's own observations. An FBI hair examiner testified that a hair on a towel found with the body matched Bolin's, and an FBI agent testified that mitochondrial DNA from Bolin's hair and saliva matched a profile found on the body. Collins's mother identified her daughter's clothing. Two witnesses described seeing her in the white van, and a friend of his former wife and her new husband said he had seen Bolin use a white van years before. The note in her purse matched his truck.
For the sentence the court found one aggravating factor, his earlier convictions for violent felonies: the Matthews murder, the Ohio kidnapping and rape, and the Ohio assault and escape. It weighed against it the mitigation, including child abuse and an 11-year marriage, and found that the aggravation far outweighed it.
On February 21, 2013, the Florida Supreme Court affirmed the conviction and death sentence (Bolin v. State, 117 So. 3d 728). The justices held that playing the redacted testimony from the first trial did not violate his right to confront witnesses, because his lawyers had cross-examined her thoroughly then; that the jail letter had been lawfully seized and properly admitted; that the evidence supported premeditated murder; and that the death sentence was proportionate.
Bolin spent 23 hours a day alone in a six-by-nine-foot cell at Florida State Prison, ABC News reported in 2015. Death row allowed no conjugal visits. In an interview for 20/20 that August, he denied the killings and could not say where he had been on the nights they took place. Of the Ohio crime, to which he had pleaded guilty, he said: "I was a very angry man 27 years ago. Twenty-seven years later, would I do the same thing? No." He told 20/20 that the victims' families had never heard evidence that he believed would clear him, the AP reported.
In 2014 an inmate in Ohio contacted Rosalie Bolin about another Ohio inmate, S.K. (he was never charged), who was said to have confessed to killing Teri Lynn Matthews. On September 26, 2014, Bolin filed a new postconviction motion based on that confession, according to the Florida Supreme Court. S.K. took his own life before a scheduled evidentiary hearing; the AP placed his death in late 2014. The inmate who had passed on the story refused to testify, and another witness testified that S.K. had told him the confession was false. Prosecutors said S.K. had falsely confessed to other crimes, NBC News reported.
The courts also ordered DNA testing. The results, completed on August 26, 2015, excluded S.K. and did not exclude Bolin, the Florida Supreme Court recorded. The circuit court denied the amended motion on October 19, 2015, after a hearing.
A second line of argument concerned Michael Malone, a former FBI hair and fiber examiner whose work had been discredited in other cases. Prosecutors said the problems with his work had been known since a 1997 report by the Justice Department's inspector general; Bolin's lawyer, Bjorn Brunvand of Clearwater, said a 2014 government notice had listed Bolin's case for review, NBC News reported. The Florida Supreme Court found the claim untimely and without merit, because Malone's work in the Matthews case had been limited and no analysis by him had been presented to the jury.
Governor Rick Scott signed Bolin's death warrant on October 30, 2015, for the murder of Teri Lynn Matthews, and set the execution for January 7, 2016. On December 30, 2015, the day she would have turned 55, her mother brought flowers with a copy of the signed warrant rolled inside, NBC News and Patch reported. "It's the last thing I can do for her," she said. She was 78, widowed, and had outlived three of her children. She told NBC that she was always prepared for Rosalie to pull a rabbit out of a hat.
On December 17, 2015, the Florida Supreme Court affirmed the denial of relief (Bolin v. State, No. SC15-2149, reported at 184 So. 3d 492). It held that the S.K. confession would probably not produce an acquittal or a lighter sentence given the strength of the evidence, that neither the confession nor the Malone material had been suppressed by the state in a way that mattered, and that the governor's choice of when to sign the warrant did not violate due process. A federal district court also denied a stay. On Monday, January 4, 2016, a three-judge panel of the Eleventh Circuit Court of Appeals refused to halt the execution, CBS Miami and the News Service of Florida reported.
Teri Lynn's mother said the families had been put through hell by the years of appeals, and she blamed Rosalie Bolin in part, the AP reported. She would consider forgiveness, she said, only if he admitted his guilt or showed remorse.
The day before his execution Bolin told the Tampa station Fox 13 that he was innocent. "I didn't know 'em, never seen 'em, never met 'em," he said of the three women, according to the AP. He said the evidence had been tampered with and planted. "My conscience is clear," he said, according to Inside Edition. "Florida's just killing me."
On his last day he visited with his wife and his spiritual adviser, and corrections officials described him as calm, the AP reported. His last meal was steak, a baked potato, salad and lemon meringue pie.
The execution was set for 6 p.m. at Florida State Prison in Starke. It waited for nearly four hours while the United States Supreme Court considered his final petition and application for a stay. Shortly before 10 p.m. the court denied both without comment (Bolin v. Jones, Nos. 15-7662 and 15A699). Asked whether he wished to make a final statement, Bolin said, "No, sir." The procedure took about 12 minutes, and he was pronounced dead at 10:16 p.m., according to the governor's office. He was 53. It was the first execution in the United States in 2016, the Death Penalty Information Center records; Florida used a three-drug protocol beginning with midazolam.
Teri Lynn's mother and Stephanie's family were among the witnesses. Afterward several dozen relatives and friends of the three women gathered outside the prison. Teri Lynn's mother said the execution was not a celebration but that she felt relief, and that she would die knowing she had closure. It did not matter to her that he was executed for only one of the three killings, she said, because "he only dies once. He dies for all of our girls."
Brunvand wept as he spoke to reporters. He said he could not imagine the families' pain, but called executions barbaric and said, "This is not the solution." In an emailed statement Rosalie Bolin accused the state of executing an innocent man on the strength of perjury, police misconduct and tainted FBI evidence, and called the execution "barbaric in a civilized society."
Oscar Ray Bolin Jr. is dead; he was executed on January 7, 2016. At his death the death sentence in the Collins case also stood, affirmed in 2013, and the life sentence in the Holley case was in force. No court has set aside any of the three final convictions.
Proven by final judgment: the first-degree murders of Teri Lynn Matthews (verdict October 24, 2001; affirmed 2004) and Stephanie Collins (affirmed 2013), and the second-degree murder of Natalie Blanche Holley (verdict April 2012; life). In Ohio he pleaded guilty in 1988 to kidnapping and rape and to felonious assault and escape.
Never charged: the 1987 death of Deborah Diane Stowe in Greenville, Texas. The AP reported that a cousin told authorities he and Bolin abducted her and that Bolin killed her, and that Texas prosecutors declined to seek an indictment. It is attributed, not proven. Patch wrote in 2015 that he was suspected in other killings across the country; no such case has been named in the reporting.
Denied by Bolin: all three Florida killings. His claim that an Ohio inmate committed the Matthews murder was rejected by the Florida courts and the federal courts, and DNA testing in 2015 excluded that inmate.
Details that vary between sources: whether Collins disappeared in November 1986 (court records, November 5) or October 1986 (some AP stories); the date of the third Collins verdict (November 2, 2006, in the Florida Supreme Court's 2013 opinion; November 30, 2007, in the Commission on Capital Cases summary) and whether a jury recommended death at that trial; the Ohio sentence (22 to 75 years, AP; 25 to 75 years, ABC News); the number of trials (ten guilty verdicts from ten juries, AP; "seven murder trials," ABC News, 2015); whether Matthews's car was found that morning (NBC News) or the next day (Florida Supreme Court, 2010); and the spelling of her surname, which some court and commission records give as Mathews.
January 22, 1962: Oscar Ray Bolin Jr. is born.
January 25, 1986: Natalie Blanche Holley, 25, is abducted after leaving work in Tampa; her body is found that morning.
November 5, 1986: Stephanie Collins, 17, disappears in Tampa.
December 5, 1986: Teri Lynn Matthews, 26, is taken from outside the Land O' Lakes post office; her body is found in rural Pasco County, and Collins's body is found in Hillsborough County the same day.
1987: kidnapping near Toledo, Ohio; death of Deborah Diane Stowe in Greenville, Texas (never charged).
1988: guilty pleas in Ohio to kidnapping and rape, and to felonious assault and escape.
July 1990: his former wife's new husband calls Crime Stoppers in Fort Wayne, Indiana.
August 1, 1990: indicted in Hillsborough County in the Holley and Collins cases.
February 19, 1991: indicted in Pasco County in the Matthews case.
June 22, 1991: suicide attempt in the Hillsborough County jail; the letter to Captain Gary Terry is found.
July 11, 1991: guilty verdicts in the first Holley trial; death sentence July 31.
October 11, 1991: guilty verdict in the first Collins trial; death sentence.
October 12, 1992: guilty verdict in the first Matthews trial; death sentence October 30.
1992: his former wife dies.
April 21, 1994: Florida Supreme Court reverses the Holley convictions.
February 9, 1995: Florida Supreme Court reverses the Collins and Matthews convictions.
1996: marries Rosalie Martinez in a wedding carried on television.
August 21, 1996: guilty verdict in the second Matthews trial; death sentence October 9.
February 18, 1999: guilty verdicts in the second Holley trial.
April 8, 1999: guilty verdicts in the second Collins trial.
June 4, 1999: death sentences in the Holley and Collins cases.
June 10, 1999: Florida Supreme Court reverses the second Matthews conviction.
July 13 and August 30, 2001: Florida Supreme Court reverses the second Collins and Holley convictions.
October 24, 2001: guilty verdict in the third Matthews trial; death sentence December 28.
February 5, 2004: Florida Supreme Court affirms the Matthews conviction and death sentence.
October 7, 2005: third Holley jury returns second-degree murder; life sentence October 11.
November 2006 or November 2007: guilty verdict in the third Collins trial; death sentence December 2007.
March 20, 2009: Second District Court of Appeal orders a fourth Holley trial.
July 1, 2010: Florida Supreme Court affirms denial of postconviction relief in the Matthews case.
April 2012: fourth Holley jury returns second-degree murder; life sentence. Holley's mother dies the same year.
February 21, 2013: Florida Supreme Court affirms the Collins conviction and death sentence.
July 1, 2013: federal district court denies habeas corpus in the Matthews case.
September 26, 2014: new motion based on another Ohio inmate's confession.
August 26, 2015: DNA results exclude that inmate and do not exclude Bolin.
October 30, 2015: Governor Rick Scott signs the death warrant.
December 17, 2015: Florida Supreme Court affirms denial of relief.
January 4, 2016: Eleventh Circuit refuses a stay.
January 7, 2016: the U.S. Supreme Court denies a stay; Bolin is executed at Florida State Prison and pronounced dead at 10:16 p.m.