Dylan Dougherty Stanley is the oldest of the three Florida half-siblings known as the Dougherty Gang, who carried out a week-long crime spree across Florida, Georgia, and Colorado in August 2011. He was 26 at the time, fired an AK-47-style rifle during both a Florida police chase and a Georgia bank robbery, shot at Colorado troopers from a fleeing car, and later tried to break out of a Colorado jail. He drew a 32-year Colorado prison term and a 428-month federal sentence, part of which was later vacated on appeal.
Background and Why the Siblings Ran
Dylan lived in Lacoochee, a small Pasco County community in Florida, with his half-siblings Lee Grace Dougherty, then 29, and Ryan Edward Dougherty, then 21. Their mother, Barbara Bell, said Dylan had “the shortest police record” of the three, though between them the siblings had 20 felonies on their records for offenses including drug possession, battery, and burglary.1BBC News. Dougherty Gang Siblings2ABC News. Report: Dougherty Sibling Planned Jailbreak
The trigger for the run was Ryan’s legal exposure. He had been convicted of sending explicit text messages to an 11-year-old girl and was on sex offender registration and probation.3ABC News. Fugitive Dougherty Gang Sighted in Colorado In later court statements, the siblings said they planned to flee the country, with accounts varying between Belize and Mexico, so Ryan could escape those obligations. Before leaving Florida they packed a Subaru Impreza with ten guns and roughly 2,000 rounds of ammunition, and Ryan cut off his court-ordered ankle monitor.4NBC News. In Court, Dougherty Siblings Explain Cross-Country Crime Spree
What Dylan Did During the Spree
Zephyrhills, Florida: Shooting at a Patrol Car
On August 2, 2011, Officer Kevin Widner of the Zephyrhills Police Department tried to stop the white Subaru for speeding. The siblings led him on a five-mile chase at speeds reaching 100 miles per hour and fired roughly 20 shots at his patrol car, flattening one tire in a convenience store parking lot. Widner was not hit and did not return fire. Investigators tied the siblings to the shooting after finding Ryan’s discarded ankle monitor near the scene.5CBS News. Dougherty Siblings Chase Video Released by Police in Fla.6HuffPost. Dougherty Siblings Fugitives
Valdosta, Georgia: Bank Robbery
Later the same day, about 200 miles north, the three walked into a CertusBank branch in Valdosta wearing masks and black clothing. Dylan carried an AK-47-style rifle and fired a round into the ceiling. Lee Grace, with a 9mm machine pistol, also fired into the ceiling. Ryan put $5,168 from the teller drawers into a tool bag.7CNN. Three Siblings Manhunt8CBS News. Dougherty Gang Sentenced to 35 Years for Georgia Bank Robbery
Colorado: Shootout and Capture
Federal warrants went out on August 4, and the siblings’ photos appeared on billboards across the Southeast. On August 9, a Walmart clerk in Cañon City, Colorado, refused to sell them AK-47 ammunition and alerted authorities after recognizing them from the news.9NBC News. Dougherty Gang Ammunition Purchase Attempt
The next morning, a Colorado State Patrol trooper picked up the Subaru south of Pueblo. The chase ran about 20 miles along Interstate 25 at speeds up to 100 miles per hour, with at least one sibling leaning out of the car to fire an AK-47 at the troopers. Prosecutors later said Dylan fired 11 shots at pursuing officers.4NBC News. In Court, Dougherty Siblings Explain Cross-Country Crime Spree The troopers did not return fire during the pursuit.10Daily Camera. Dougherty Gang Captured
The pursuit ended near Walsenburg when the car flipped and came to rest on a guardrail. Lee Grace pointed a machine pistol at Walsenburg Police Chief James Chamberlain, who shot her in the leg. One brother was taken at the crash site; the other ran and was tackled by civilian highway workers. Officers recovered two AK-47 rifles and a MAC-11 pistol from the wreckage.11ABC News. Dougherty Gang Fugitive Siblings Captured by Colorado Highway Workers12CBS News. 3rd Dougherty Sibling Responsible for Crime Spree Sentenced
The Jail Escape Plan
Held at the Huerfano County Jail in Walsenburg while awaiting trial, Dylan plotted a breakout. During a cell search on January 10, 2012, deputies found that he had tampered with a plumbing access panel and used ceiling space to move between cells, and that he had passed a note to Lee Grace in the women’s section. The note described dropping into the detention control room, overpowering the guards, taking their keys, and freeing his sister. Deputies also recovered a homemade knife and a letter addressed to the FBI from his cell.13Denver Post. Document: Dougherty Sibling Planned Colo. Escape He was moved to the Pueblo County Jail and charged with conspiracy to escape and possession of contraband.2ABC News. Report: Dougherty Sibling Planned Jailbreak
Sentencing
Colorado State: 32 Years
On April 30, 2012, Chief District Judge Claude Appel sentenced all three siblings in Huerfano County District Court. Dylan pleaded guilty to one count of first-degree assault for firing at police during the Colorado chase and received the maximum, 32 years in state prison, with credit for 265 days already served. Lee Grace received 24 years; Ryan received 18.14Pueblo Chieftain. Siblings Get Combined 74 Years15Jacksonville.com. 1 of 3 Florida Siblings Charged in Multi-State Crime Spree Gets Prison
Federal: 428 Months for the Bank Robbery
On December 17, 2012, Senior District Judge Hugh Lawson sentenced all three siblings in the U.S. District Court for the Middle District of Georgia in Valdosta. Each got 428 months, roughly 35 years and 8 months, plus five years of supervised release: 228 months for the bank robbery count and 200 months for using, carrying, and discharging a firearm during a crime of violence, running consecutively. The federal system has no parole. The three were jointly ordered to pay $1,738 in restitution to CertusBank.16U.S. Department of Justice. Dougherty Gang Sentencing Press Release As part of the federal plea deal, the Colorado state sentences were vacated, with Judge Appel keeping jurisdiction to reimpose them if needed, so the time could run concurrently across jurisdictions.17Jacksonville.com. Florida Siblings Sentenced to More Than 35 Years in Jail
Florida also charged the siblings over the Zephyrhills shooting, including attempted second-degree murder of a law enforcement officer, fleeing to elude, and grand theft auto. The available research reports the Florida resolution for Ryan but not separately for Dylan.
The Appeal That Undid Part of the Federal Sentence
Dylan appealed. On June 20, 2014, the U.S. Court of Appeals for the Eleventh Circuit vacated his federal sentence, along with Lee Grace’s, finding that the district court had wrongly applied a six-level sentencing enhancement for assaulting a law enforcement officer during “immediate flight” from the bank robbery. The enhancement had rested on the Colorado shootout, which took place eight days later and thousands of miles away. The court wrote that “there’s nothing ‘immediate’ about eight days later” and sent the cases back for resentencing.18Justia. United States v. Dougherty, No. 12-16540 Ryan’s identical sentence was affirmed because he had waived the procedural challenge.19FindLaw. United States v. Dougherty
The available research does not report the revised sentence Dylan received on remand.