It’s estimated he’s spent $30 million on legal defense over the past decade, disputing a variety of charges. He’s able to afford these staggering bills due to the success of his rap career, which includes lucrative brand endorsements as well as chart-topping music.

Mill granted a revealing interview to Rolling Stone from prison this week, in which he discusses some of these issues, as well as the judge whom many feel has treated him unfairly and has a personal grudge against him. The day the interview came out, a motion was filed by prosecutors stating there is a “strong likelihood” the rapper’s conviction would be reversed.

Unsurprisingly, trying to untangle the story of where his troubles began can be confusing. Here’s a timeline to help sort things out.

2004: A teenage Meek, after several years battle-rapping on the streets of Philadelphia, joins rap group the Bloodhoundz.

2008: Meek is charged with illegal possession of a firearm and drug possession after police find a gun on him while he is walking to the corner store. He claims he is violently beaten, but he is charged with assault in return by the police.

2008: Meek meets his nemesis, Judge Genece Brinkley, for the first time. He faces 19 counts; Brinkley finds him guilty of seven, most of them gun-related. He is given an unusually harsh sentence of two years in jail and eight on probation. Several days later, his first solo mixtape, Flamers, comes out.

2009: Meek is released to house arrest and signs a management deal with former Will Smith bodyguard Charlie Mack, who assists with his legal issues. He releases and appears on a series of mixtapes, eventually putting out his first album in 2012.

https://www.youtube.com/watch?v=S8gfqs1-NuE

2012: En route to the airport while promoting the new album, he’s pulled over by police because of his tinted windows. They believe they smell marijuana coming from the car. After refusing to allow them to search his car, Meek is arrested and held overnight.

A month later, he faces a violation of probation hearing, in which Judge Brinkley orders drug tests (he passes) and forbids him to continue his tour. He continues booking dates anyway, so he appears before the judge again in December and is ordered to stay home for the holidays.

2013: Meek appears in court in March for a hearing related to a possible probation violation as alleged by his probation officer, who says he left the state without providing a detailed itinerary. The rapper explains this by saying that his schedule changes rapidly. He asks for a new probation officer, but that request is denied.

In June, he faces similar violation issues. Additionally, the judge orders that he take etiquette courses after references to his probation officer on social media drive fans to send the officer death threats.

2014: Judge Brinkley revokes Meek’s parole as a result of behavior that is deemed “questionable,” and which reportedly includes his social media activity as well as testing positive for Percocet (he claims he used it following oral surgery). He ends up serving five months in jail.

2015: In December, Meek is found guilty yet again of violating probation. Brinkley forbids him to work or perform until his sentencing in February 2016.

2016: He avoids a prison term at the sentencing but is forced to endure 90 days of house arrest instead, during which he is again forbidden to work.

2017: About a year later, Meek gets into a fight when an airport employee attempts to take a picture with him. He’s charged with misdemeanor assault, but the charges are eventually dropped.

A few months later, some videos capturing Meek doing stunts on a dirt bike go viral on social media, resulting in police charging him with reckless endangerment. This charge — a felony — is also dropped on condition he stay out of trouble for a few months and do community service.

However, the cumulative effect of these incidents spurs a parole hearing, in which Brinkley hands down a sentence of two to four years in prison for violating probation. Brinkley is clearly exasperated, saying she’d been trying to help Meek for years but that he keeps “thumbing his nose” at the court. Meek’s lawyers vow to appeal the decision.