The combination of an upper level impulse and southward sagging frontal boundary out of the Ohio Valley brought a line of strong to severe thunderstorms across eastern Kentucky. The most intense of these storms moved through far eastern Kentucky, including Prestonsburg where a 70-80 mph downburst blew half the roof off of a hock shop building.
A man driving on West Court Street was crushed by this roof, resulting in his death. Damage stretched for about 1 mile through the city. Severe winds blew out a few of the windows of a 2 story building on West Court Street, while a large healthy poplar tree was uprooted.
Elsewhere, from West Liberty and Jackson eastward through Pike County, mainly tree damage was sustained. In Letcher County, a rotating supercell produced quarter to golf ball sized hail near Jenkins, while Somerset experienced isolated damage from a thunderstorm wind gust on the southwest flank of the line of storms.

Hail in MORGAN, KENTUCKY
From 29-MAY-19 12:09:00 to 29-MAY-19 12:09:00 (EST-5)
Location: CROCKETT
Magnitude: 0.75 
Property damage: 0.00K
Crop damage: 0.00K
Reported by: 911 Call Center

Dispatch reported penny sized hail in Crockett.

Thunderstorm Wind in FLOYD, KENTUCKY
From 29-MAY-19 13:23:00 to 29-MAY-19 13:23:00 (EST-5)
Location: SALISBURY
Magnitude: 53.00 EG
Reported by: Fire Department/Rescue

Fire Rescue officials observed trees and limbs downed south of Arkansas.

Thunderstorm Wind in MAGOFFIN, KENTUCKY
From 29-MAY-19 12:52:00 to 29-MAY-19 12:52:00 (EST-5)
Location: MASON
Magnitude: 53.00 EG
Reported by: 911 Call Center

Dispatch reported multiple trees blown down along Kentucky Highway 7 south of Salyersville near the Mason area.

Thunderstorm Wind in FLOYD, KENTUCKY
From 29-MAY-19 13:15:00 to 29-MAY-19 13:15:00 (EST-5)
Location: ALLEN
Magnitude: 57.00 EG
Property damage: 25.00K
Reported by: Trained Spotter

A trained spotter observed a tree blown over onto a house in Allen.

Hail in PERRY, KENTUCKY
From 29-MAY-19 14:37:00 to 29-MAY-19 14:37:00 (EST-5)
Location: LEATHERWOOD
Magnitude: 0.75 
Property damage: 0.00K
Crop damage: 0.00K
Reported by: Trained Spotter

A SKYWARN Spotter observed penny sized hail northeast of Leatherwood.

Thunderstorm Wind in MORGAN, KENTUCKY
From 29-MAY-19 12:12:00 to 29-MAY-19 12:12:00 (EST-5)
Location: ELDER
Magnitude: 50.00 EG
Reported by: 911 Call Center

Dispatch reported trees blown down west of West Liberty, including near the intersection of Tabernacle Road and Kentucky Highway 705.

Thunderstorm Wind in BREATHITT, KENTUCKY
From 29-MAY-19 12:44:00 to 29-MAY-19 12:46:00 (EST-5)
Location: ELKATAWA
Magnitude: 51.00 EG
Reported by: Public

Citizens reported trees blown down in and southwest of Jackson.

Thunderstorm Wind in FLOYD, KENTUCKY
From 29-MAY-19 13:08:00 to 29-MAY-19 13:10:00 (EST-5)
Location: WEST PRESTONSBURG
Magnitude: 56.00 EG
Property damage: 25.00K
Reported by: Emergency Manager

Emergency Management reported tree damage southwest of Prestonsburg, including one falling on a house as well as the top of a pear tree being broken off.

Thunderstorm Wind in FLOYD, KENTUCKY
From 29-MAY-19 13:30:00 to 29-MAY-19 13:30:00 (EST-5)
Location: BOLDMAN
Magnitude: 51.00 EG
Reported by: Broadcast Media

Broadcast media relayed a report of a tree being uprooted in Harold.

Thunderstorm Wind in MAGOFFIN, KENTUCKY
From 29-MAY-19 12:53:00 to 29-MAY-19 13:00:00 (EST-5)
Location: CYRUS
Magnitude: 52.00 EG
Reported by: NWS Employee

An NWS Employee and local media relayed reports of trees and large limbs blown down from Cyrus through Ivyton.

Thunderstorm Wind in FLOYD, KENTUCKY
From 29-MAY-19 13:11:00 to 29-MAY-19 13:13:00 (EST-5)
Location: PRESTONSBURG
Magnitude: 70.00 EG
Property damage: 155.00K
Crop damage: 10.00K
Reported by: NWS Storm Survey

A National Weather Service Meteorologist surveyed localized downburst winds in Prestonsburg. These winds caused sporadic damage throughout the community. The highest wind gust estimated was in downtown Prestonsburg on West Court Street
where one half of the roof of a hock shop building was lifted off. This roof landed on West Court Street, including on multiple vehicles, fatally wounding one person in a moving vehicle. Glass was also broken on multiple windows on the north side of the building. There were a number of other buildings and homes with minor roof
or gutter damage nearby, as well as a couple of uprooted trees near the downtown area. A HAM radio tower that had been mounted on the top of the annex building beside the jail and behind the courthouse in downtown Prestonsburg was also destroyed by thunderstorm wind gusts. The winds snapped the support wires that had been holding up the tower causing the tower to break in half and fall onto the roof of the building it had been mounted on and the ground next to the building. Wind speeds that uprooted a tree at a residence on South Highland Avenue were estimated to be in the upper end of the 70 to 80 mph range.

Thunderstorm Wind in PIKE, KENTUCKY
From 29-MAY-19 13:35:00 to 29-MAY-19 13:38:00 (EST-5)
Location: BROAD BOTTOM
Magnitude: 55.00 EG
Property damage: 5.00K
Reported by: Emergency Manager

Local Emergency Management reported a roof blown off of a carport on Venters Lane north of Pikeville, along with numerous trees blown down throughout Pikeville.

Thunderstorm Wind in PIKE, KENTUCKY
From 29-MAY-19 13:38:00 to 29-MAY-19 13:38:00 (EST-5)
Location: HATFIELD
Magnitude: 52.00 EG
Reported by: 911 Call Center

Dispatch reported a tree was blown down onto a power line near Hatfield Station.

Thunderstorm Wind in PULASKI, KENTUCKY
From 29-MAY-19 13:39:00 to 29-MAY-19 13:40:00 (EST-5)
Location: NANCY
Magnitude: 50.00 EG
Reported by: Emergency Manager

Local Emergency Management reported trees were blown down and onto Kentucky Highway 80 between Nancy and Somerset. A pontoon boat was blown off of Lake Cumberland at Pulaski County Park.

Thunderstorm Wind in PIKE, KENTUCKY
From 29-MAY-19 13:56:00 to 29-MAY-19 13:57:00 (EST-5)
Location: SIMERS
Magnitude: 51.00 EG
Reported by: Broadcast Media

Local media and dispatch relayed reports of trees blown down near Johns Creek east of Kimper and in the Mudlick community northeast of McAndrews.

Thunderstorm Wind in PIKE, KENTUCKY
From 29-MAY-19 13:58:00 to 29-MAY-19 13:58:00 (EST-5)
Location: MC VEIGH
Magnitude: 56.00 EG
Reported by: Emergency Manager

The county Emergency Manager reported a large oak tree was blown down by thunderstorm wind gusts west of Phelps. The tree fell onto the guide wires of a large radio tower nearby, causing the tower to fall to the ground as well.

Thunderstorm Wind in LETCHER, KENTUCKY
From 29-MAY-19 14:12:00 to 29-MAY-19 14:12:00 (EST-5)
Location: EAST JENKINS
Magnitude: 50.00 EG
Reported by: Trained Spotter

A tree was blown down and onto Kentucky Highway 805 northeast of Jenkins, blocking the road.

Hail in LETCHER, KENTUCKY
From 29-MAY-19 14:12:00 to 29-MAY-19 14:14:00 (EST-5)
Location: BEEFHIDE
Magnitude: 1.75 
Property damage: 0.00K
Crop damage: 0.00K
Reported by: Trained Spotter

A trained spotter and local media reported quarter to golf ball sized hail northeast of Jenkins, including along U.S. Highway 23.