Dominion of New York

Social Justice

July 12, 2012

Law Review Article Analyzes Jay-Z’s 99 Problems

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Written by: Kelly Virella


ou know the knack that some writers have for dissecting pop-culture news with an air of professorial authority, for turning Brittany Spears into a worthy topic for dissertation? Well this week, America met a new such a writer in the form of Southwestern Law School professor Caleb Mason who has written a paper analyzing the Jay-Z song “99 Problems.” It’s a brilliant, and eye-opening much-blogged-about introduction to the thinking of criminal defense lawyers. Until I read it, it never occurred to me that criminal defenders are essentially an organized force of resistance to the Drug War.

“In one compact, teachable verse (Verse 2), the song forces us to think about traffic stops, vehicle searches, drug smuggling, probable cause, and racial profiling, and it beautifully tees up my favorite pedagogical heuristic: life lessons for cops and robbers,” Mason says before launching into a line-by-line exegesis of the verse.

What’s eye-opening is seeing Mason give avowed drug dealers advice about fighting their charges. Here’s his take on this Jay-Z line: “In my rearview mirror is the motherfucking law/I got two choices y’all, pull over the car or/Bounce on the double put the pedal to the floor.”

Mason says:

The calculation Jay-Z has to make is whether, knowing that the car contains concealed contraband, he’s better off trying to flee or hoping that the police won’t find the drugs during the stop. This may be the hardest choice perps face (until they have to decide whether or not to cooperate), but there’s only one answer: you are always better off having drugs found on you in a potentially illegal search than you are fleeing from a potentially illegal search and getting caught. The flight will provide an independent basis for chasing and arresting you, and the inadequacy of the quantum of suspicion supporting the initial attempted seizure will not taint the contraband discovered if there is an intervening flight. Law students: practice explaining the preceding sentence to a layperson. Smugglers, repeat after me: you have to eat the bust, and fight it in court.

The Drug War opponent in me applauds Mason’s advice and is grateful that low level dealers have an escape valve. The Puritan in me is appalled and wants to see them punished. Go figure.

Jay-Z’s 99 Problems, Verse 2: A Close Reading With Fourth Amendment Guidance for Cops & Perps

About the Author

Kelly Virella
Kelly Virella lives in an East Harlem walk-up with her husband, her bicycle and her books. She's worked as a journalist for 11 years and started this website during the summer of 2011. She fell in love with New York City during her first visit here as a 16-year-old and finally made good on her promise to move here in April 2010.


New York City Mayor Michael Bloomberg and NYPD Commissioner Ray Kelly, left to right. Photo courtesy of Flickr/Azipaybarah