James Dailey: 1985 Killing, Jailhouse Informants, and Appeals

The James Dailey death row case is a Florida capital prosecution in which a man has spent nearly four decades awaiting execution for the 1985 murder of 14-year-old Shelly Boggio, based on a conviction that rested almost entirely on three jailhouse informants — including a serial informant later described by police as a “con man extraordinaire” — with no physical or forensic evidence tying Dailey to the killing, and with his co-defendant Jack Pearcy repeatedly claiming, then retracting, sole responsibility.¹

The 1985 Killing and What Tied Dailey to It

On an evening in May 1985 near St. Petersburg, Shelly Boggio, her twin sister Stacey, and a friend were hitchhiking when they were picked up by James Dailey, Jack Pearcy, and Dwayne “Oza” Shaw. The group went to a bar. Stacey and the friend went home. Shelly returned with Dailey and Pearcy to the house where the two men were living.²

By Shaw’s later account, he drove out with Pearcy and Boggio, was dropped at a phone booth, and Pearcy and Boggio drove off alone. When Pearcy and Dailey came back to the house together later that night, Boggio was no longer with them, and Shaw noticed Dailey’s pants were wet.² Boggio’s nude body was found in the water near Indian Rocks Beach. She had been stabbed repeatedly, strangled, and drowned. The murder weapon was never recovered.³

Pearcy was tried first, in 1986, and convicted of first-degree murder. He received a life sentence.³ Dailey was tried separately in 1987 in Pinellas County. There were no eyewitnesses, no fingerprints, and no forensic evidence connecting him to Boggio’s death. The lead prosecutor later conceded in a filing: “It was a circumstantial case, it’s not like there was an upstanding citizen eyewitness to the case. So speculation is all we have as to what happened.”⁴

The state’s case rested on three pieces: Shaw’s testimony about the wet pants, a post-arrest statement from Pearcy implicating Dailey, and testimony from three jailhouse informants who said Dailey confessed while awaiting trial.³ The jury convicted, and Dailey was sentenced to death on August 7, 1987.⁵

The Three Jailhouse Informants

The inmates who said Dailey confessed were James Leitner, Pablo DeJesus, and Paul Skalnik. Leitner told the jury Dailey said, “I’m the one that did it” and “Man, I just lost it.” DeJesus said Dailey called himself “the one that killed the girl.” Skalnik testified that Dailey described the victim as “screaming, staring at me, and would not die.”⁵

Another inmate, Travis Smith, later testified he had seen DeJesus and Leitner “trying to collaborate a story together” for sentence reductions, and that it was widely known in the Pinellas County Jail that Detective John Halliday was seeking testimony against Dailey. Both Leitner and DeJesus received plea deals letting their Florida sentences run concurrently with sentences from other states, so they served no additional Florida time.⁶

Paul Skalnik

Skalnik’s role is the most contested. A former police officer turned serial fraudster and registered sex offender, he provided testimony or information in at least 37 cases in Pinellas County between 1981 and 1987, contributing to four death sentences.⁷ Between January and June 1987 alone, he obtained alleged confessions in four first-degree murder cases.¹

The benefits Skalnik received were substantial. A molestation charge was dismissed. He was paroled midway through a five-year sentence despite being classified as a “high risk of further unlawful behavior.” Detective Halliday wrote to the parole board on his behalf, something Halliday acknowledged he had never done for any other inmate. None of these benefits, and none of Skalnik’s expectation of receiving them, were disclosed to Dailey’s defense at trial.⁶¹ The prosecution cited Skalnik’s testimony more than a dozen times during closing arguments, calling him “honest” and “reliable.” Five days after Dailey was sentenced to death, Skalnik was released from jail.⁸

Defendants in cases where Skalnik testified frequently said they had never met or spoken with him. By 2015, when Skalnik was arrested for failing to register as a sex offender and possessing fraudulent documents, a sheriff’s investigator stated: “I would never be able to say on the stand that I believed the information he gave me was true and credible.”⁷ ABC News later reported that original prosecutor Robert Heyman acknowledged the prosecution knew a sexual assault charge was in Skalnik’s criminal history, which contradicted Skalnik’s trial testimony that he had never been involved in rape or violence. Prosecutors did not correct that testimony.⁹

Jack Pearcy’s Shifting Confessions

Whether Dailey was even present at the killing turns largely on his co-defendant, whose story has changed repeatedly. At the time of his arrest, Pearcy told authorities that Dailey killed Boggio and that he himself had been asleep in his car.¹⁰ He refused to testify at Dailey’s 1987 trial.¹¹

In April 2017, Pearcy signed an affidavit stating: “James Dailey was not present when Shelly Boggio was killed. I alone am responsible for Shelly Boggio’s death.” At a later evidentiary hearing, he testified the affidavit was not true and invoked the Fifth Amendment, making himself unavailable for cross-examination.¹¹

In December 2019, Pearcy signed a second declaration: “James Dailey had nothing to do with the murder of Shelly Boggio. I committed the crime alone. James Dailey was back at the house when I drove Shelly Boggio to the place where I ultimately killed her.” At a February 2020 deposition, he denied that declaration too, saying he had lied to prevent Dailey’s execution and to keep Dailey’s attorneys working the case in the hope they might turn up evidence useful to Pearcy’s own exhausted appeals.²

At an evidentiary hearing on March 5, 2020, Pearcy refused to testify at all. He told the judge: “I’ve done 35 years for a crime I didn’t commit and I don’t plan on testifying against somebody else to help the state kill them.”¹²

Where the Appeals Stand

Dailey’s post-conviction fight has run through both state and federal courts, centered on three arguments: that Pearcy was the sole killer, that prosecutors withheld exculpatory evidence, and that the informant testimony was unreliable.

In 2019, the Florida Supreme Court rejected Dailey’s first post-conviction challenge based on Pearcy’s 2017 affidavit, ruling the affidavit was inadmissible hearsay that did not qualify as a statement against interest and did not meet the standards for third-party guilt admission under Chambers v. Mississippi.¹³

After Pearcy’s 2019 declaration, Pinellas-Pasco Circuit Judge Pat Siracusa granted a new evidentiary hearing on February 20, 2020.⁹ That hearing collapsed when Pearcy refused to testify and his deposition recanting the declaration was weighed against it. The trial court denied the motion for a new trial on May 29, 2020.¹⁴

On September 23, 2021, the Florida Supreme Court denied Dailey’s post-conviction challenge for the final time at the state level. The court held that Pearcy’s written declarations were inadmissible and that his February 2020 deposition “completely invalidates” the claim that Pearcy alone was responsible. It also rejected claims that prosecutors knowingly elicited false testimony from Skalnik about his criminal history. Justice Jorge Labarga dissented, writing that the conviction was “compromised by a cloud of unreliable inmate testimony” and pointing to the total lack of forensic evidence corroborating the informants.¹⁵

In federal court, the U.S. Court of Appeals for the Eleventh Circuit denied Dailey’s application on January 30, 2020 to file a second or successive habeas petition, finding he had not made a sufficient showing on actual innocence and prosecutorial misconduct. Chief Judge Ed Carnes acknowledged in the ruling that Skalnik’s trial testimony was “likely false” but concluded that the statutory burden for actual innocence was not met.¹⁶¹⁷

Dailey’s legal team, which includes attorney Josh Dubin and the Yale Law School Supreme Court Advocacy Clinic working with Mayer Brown LLP, has petitioned the U.S. Supreme Court for certiorari. Their filings argue that excluding Pearcy’s confessions violates due process and that the state’s failure to disclose exculpatory evidence, including a statement from former prosecutor James Slater that Pearcy had confessed and evidence that Detective Halliday offered inmates favorable treatment for incriminating Dailey, violated Brady v. Maryland. Amicus briefs supporting Dailey have come from former prosecutors and attorneys general, the U.S. Conference of Catholic Bishops, and Conservatives Concerned About the Death Penalty.¹⁸¹⁹

The 2019 Death Warrant

Florida Governor Ron DeSantis signed a death warrant on September 26, 2019 scheduling Dailey’s execution for November 7, 2019.²⁰ The U.S. District Court for the Middle District of Florida granted a stay of execution on October 23, 2019.¹⁴

Current Status

Dailey remains on Florida’s death row. The Florida Supreme Court denied his post-conviction challenge in September 2021, and his federal habeas efforts through the Eleventh Circuit have been unsuccessful.¹⁵ No new execution date has been publicly reported since the 2019 warrant was stayed. The American Bar Association, an interfaith coalition, and other organizations have called on Governor DeSantis to grant clemency, though no formal clemency hearing has been reported.²¹

Why the Case Draws National Attention

Dailey’s case has become a reference point in the broader debate over jailhouse informants. The National Registry of Exonerations reports that 7% of more than 2,500 wrongful convictions are tied to informant testimony. Several states have moved to tighten oversight: Connecticut created a statewide tracking system for jailhouse informants in 2019, Illinois in 2018 began requiring pre-trial hearings on informant reliability, and Texas now requires prosecutors to keep records of an informant’s testimony history and any benefits provided.³

A joint investigation by ProPublica and The New York Times Magazine, published in December 2019, focused on Skalnik’s career as a serial informant and helped bring the Dailey case to national attention.¹⁷

1
Death Penalty Information Center. James Dailey Faces Execution Based on Testimony of Serial Jailhouse Informant
2
Florida State University Law Library. Dailey v. State, No. SC20-1529
3
ABC News. Death Row Inmate’s Fight for Life Shines Light on Jailhouse Informants
4
Florida State University Law Library. Dailey v. State, Initial Brief on Merits
5
U.S. Supreme Court. Dailey v. Florida, Petition for Writ of Certiorari
6
Death Penalty Information Center. Dailey Motion for Post-Conviction Relief
7
Innocence Project. Jailhouse Informant Paul Skalnik
8
ProPublica. A Liar Put Him on Death Row. His Co-Defendant Could Help Set Him Free
9
Death Penalty Information Center. Florida Court Grants Hearing to James Dailey on Innocence Claim
10
ABC News. Death Row Inmate Facing Execution Based on Lying Jailhouse Informant
11
FindLaw. Dailey v. State (2019)
12
Fox 13 News. Killer Refuses to Clear Co-Defendant of Teen’s 1985 Murder
13
FindLaw. Dailey v. State (2019)
14
Death Penalty Information Center. James Dailey Case Updates
15
Death Penalty Information Center. Florida Supreme Court Denies James Dailey’s Innocence Challenge
16
FindLaw. In re James Dailey (11th Circuit, 2020)
17
ProPublica. A Liar’s Testimony Convinced a Jury to Convict a Man of Murder
18
Yale Law School. Supreme Court Clinic Files Brief on Behalf of James Dailey
19
Death Penalty Information Center. Prosecutors, Catholic Bishops, and Conservative Group Submit Brief for James Dailey
20
Florida Phoenix. Exonerated Death Row Men Will Ask Gov. DeSantis to Cancel Scheduled Execution
21
American Bar Association. James Dailey Continues to Seek Review of Innocence Claim