Chesney said despite their storm losses, the islanders still have heart: "They can not take away our heart and our spirit and how resilient everybody is, and that's one of the things that really drew me to the Island in the first place".
Chesney's home on the island of St. Thomas was destroyed when Hurricane Irma - a Category 5 storm at the time - hit St. John on Saturday (Sept. 9).
Irma, a Category 5 hurricane with 180 miles per hour winds, struck Puerto Rico on Wednesday after colliding with other Caribbean islands, and killed at least 23 people there.
"That place and the people mean so much more to me than my house".
Chesney has had homes in St. John for years - he got married to his now-ex Renee Zellweger there in 2005 - though he's normally based in Nashville and was not on the island when it was hit.
Most of the country has followed the storm on the news and on the internet, but people who live in Florida and the Caribbean islands have dealt with the storm firsthand. And I know the No Shoes Nation is mighty. "I think we're all going to come together and we're going to do so much to rebuild". Those lives have changed and will never be the same. But I want to help.
"We thought it was a very safe place for everyone because it was built with stone, concrete and bricks in an area of the island where we didn't feel like we were going to get direct wind", Chesney told HLN.
Just days after Hurricane Harvey swept through Texas, destroying and flooding everything in its path, the USA had a new storm to worry about: Hurricane Irma.
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