Its been 15 years since Michael Jackson died. The one-time megastar fell, and fell hard, in the years ahead of his death, tarnishing a legacy more than four decades in the making.

Ahead of allegations regarding Jackson’s lengthy history of child sexual abuse, he spent years at the head of the musical pack. Considered the King of Pop for much of his career, Jackson is among the best selling musical artists of all time.

Then, starting in the mid-’90s, troubling controversy arose. Jackson was taken to court on several occasions, but was ultimately acquitted on all charges. The blowback from his sordid history haunted Jackson for decades, however, leaving his once-flourishing career floundering. Add to that his untimely death in 2009, which fell just ahead of the star’s comeback tour, and the then-50-year-old’s estate was left in tatters.

How much debt did Michael Jackson have at the time of his death?

By the time he passed away, Michael Jackson had become a hugely controversial figure. Despite his acquittal, many people saw the former star as a child predator, and — while he still had support among certain followers — his fanbase had diminished immensely.

All that may have changed with the singer’s planned comeback tour, but we never got the chance to know. Jackson died before he could attempt to resuscitate his career, and his many court cases, diminished reputation, and the loss of so much revenue during his most difficult years left his bank accounts hugely in the red.

At the time of his death, Jackson was more than $500 million in debt, according to court documents filed in relation to Jackson’s estate. The massive sum was a result of Jackson’s exorbitant spending habits, as well as the massive loans he’d taken out over the years to cover various expenditures.

When he died, Jackson’s estate was hugely saddled by debt, but in the years since its executors have pulled it out of the hole his death left it in. Even after he passed, more than a dozen lawsuits had to be sorted out by the pop star’s estate, totaling millions. These days, his estate is valued over $2 billion, but it took a decade and a half to make its way out of debt, and back into the green.