It’s hard to overstate how Sean Kingston had girlies of the early 2000s in a chokehold.

The man born Kisean Paul Anderson came from a musical family: his grandfather was famed reggae producer Jack Ruby, who was best known for his work with The Toasters.

But Kingston, himself, was discovered on MySpace, according to Digital Spy, and seemed to be everywhere all at once. With hit songs like “Beautiful Girls” and “Take You There” — not to mention a guest appearance on Natasha Beddington’s “Love Like This” — Kingston’s pop-flavored brand of reggae was inescapable.

Unfortunately, according to Celebrity Net Worth, Sean Kingston is only worth $500,000 today. This, of course, is despite the fact that his songs were all over the charts at one point in the early 21st century.

Kingston’s financial difficulties didn’t come from a shady record deal or from a shady financial adviser. Rather, it came because he over-spent on things he didn’t need — and, in particular, on custom jewelry.

Let’s take a look at how Sean Kingston’s story illustrates the importance of both wealth management and living at or below your means.

Editorial note: The net worth listed in this piece is a speculative estimate drawn from a variety of online sources.

Sean Kingston: What Was His Net Worth At The Peak Of His Career?

At the height of his fame, Sean Kingston was worth $2 million.

Unpaid Bling & Lawsuits

Unfortunately, according to reports, Sean Kingston lost all his money thanks to not one, but two, lawsuits involving unpaid jewelry.

The first lawsuit came in 2014. According to The New York Daily News, the “Beautiful Girls” singer ordered two custom pieces from Avi Davidov, known in Manhattan circles as “Avi the Jeweler.” In total, Davidov claimed Kingston owed him more than $200,000 for the custom bling. Davidov ultimately won that lawsuit.

Just one year later, Kingston was allegedly kidnapped by associates of Avianne Jewelers for failing to pay for the full amount for some custom watches, per Complex.

In 2016, Sean Kingston got tangled up with NYC-based jeweler Aqua Masters, who took Kingston to court over claims that he skipped out on a $300,000 jewelry bill that included even more custom pieces. That case, too, was found in favor of the jeweler, per Complex.

As of 2020, however, a different report for Complex revealed that there was an active arrest warrant out for the Jamaica-by-way-of-Miami native for grand theft. At the time, the outlet revealed that this jeweler — whose identity hasn’t been revealed — delivered custom pieces to Kingston’s home in Florida, but Kingston never paid for the goods.

"I'm Not Broke"

In 2014, however, Sean Kingston insisted that he was still doing quite well for himself.

“People don’t see the story behind it, so they just see on TMZ that ‘Sean Kingston is being sued for jewelry, he’s broke’. How am I broke? TMZ won’t put up the fact that I just bought a house for $8 million, and I actually asked them to, but they’ll put up these lawsuits to sell this idea that I’m broke,” he said to Gulf News.