A trail of tragedy. When Eddie Montgomery's 19-year-old son died over the weekend, it became another hardship in the singer's life, something that he's unwittingly all too familiar with. Sadly, the Montgomery Gentry singer's personal life has been filled with catastrophe over the past five years.

Eddie has dealt with everything from cancer, death, divorce, bankruptcy and even natural disasters.

His trying five-year stretch of bad luck began in 2010 when he revealed that he had been diagnosed with prostate cancer. The cancer, he said at the time, was discovered very early on, a rare win considering his life. While undergoing surgery on the cancerous tumor, his wife of 20 years served him with divorce papers. They would divorce shortly after.

"U find out u got cancer then u found out ur wife can't handle that so she files for a divorce," he wrote in a now-deleted tweet in December 2010.

Tracy, Montgomery's now ex-wife, later told Lexington, Kentucky's LEX 18 News, "Despite what is being said, Eddie's cancer had absolutely nothing to do with my decision. It's what the public doesn't know that finalized an extremely difficult decision that I was forced to make."

Fast forward a few years to January 2014. The "My Town" singer filed for bankruptcy, citing debts of over $13 million from his failed restaurant, Eddie Montgomery's Steakhouse, and his divorce.

Later that same year, it seemed like Eddie's life was turning the corner and he was about to start fresh again. He married his girlfriend of three years, Jennifer Belcher, and the duo was set to begin their happily ever after. However, just days after saying "I do," the singer's home was struck by a tornado, leaving next-to-nothing in its wake.

"We'll I've had an interestin last few days," he tweeted. "I got hitched to THE @JenJenB1 and then got hit by a tornado last night!" The tweet showed a side by side images of he and his new bride next to an image of the tornado's destruction.

This week, though, it's his heart that is destroyed.

On Sept. 27, Eddie's son, Hunter, died after an accident that had him on life support in a Kentucky hospital.

"My son Hunter went to heaven today," the singer said in an emotional statement. "I appreciate all your prayers and love and thank you for giving us privacy as we grieve and say goodbye."

Few details are known about the accident that preceded that death. The Associated Press said details of what happened are being withheld "until the family is ready to release further information."

The band's official Twitter page tweeted its condolences on Sunday, writing, "Our sincerest love, thoughts and prayers are with Eddie today."

Hunter was the youngest of Eddie's four children with Tracy.