99 Problems and a Legal Analysis

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99 Problems Legal Analysis: Drugs, Traffic Stops, Fourth Amendment Search and Seizure

    Since Jay Z wrote 99 Problems in 2004, many legal analysts critiqued and praised the rap song for various aspects of criminal procedure. Professor Caleb Mason of the St. Louis University Law School provides a complete line-by-line analysis arguing that Jay-Z gets most of the legal aspects correct. As a matter of fact, Jay Z published a criticism and commentary on 99 Problems including his own notes on Verse 2.

Mason sets forth, “(i)n 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.”

From our perspective at Tower Legal, the Fourth Amendment is the legal turf that we fight most of our wars for clients. The Amendment and the cases following it are the framework for understanding whether things like police stops, blood and breath tests, search warrants, and dog sniffs are illegal or not. For cops, it’s about how to catch people who are up to something without having the arrest or any evidence thrown out. For the folks that are up to something, it’s the recipe for avoiding capture or, if captured, beating the charge. So, let’s get to Verse 2:

  1. The year’s 94 and in my trunk is raw
  2. In my rearview mirror is the motherfucking law
  3. I got two choices y’all, pull over the car or 
  4. Bounce on the double (devil) put the pedal to the floor
  5. Now i aint tryin to see no highway chase with jake
  6. Plus I got a few dollars I can fight the case
  7. So I … pull over tot he side of the road
  8. And heard, “Son do you know what I’m stopping you for?”
  9. “Cause I’m young and I’m black and my hat’s real low?
  10. Do I look like a mindreader sir, I don’t know>”
  11. Am I under arrest or should I guess some mo?
  12. Well you was doing 55 in a 54
  13. :License and registration and step out of the car
  14. Are you carrying a weapon on you, I know a lot of you are”
  15. I aint steppin out of shit, all my papers legit
  16. Do you mind if I look around the car a little bit?
  17. Well my glove compartment’s locked and so is the trunk and the back
  18. And I know my rights so you gonna need a warrant for that
  19. Aren’t you sharp as a tack, some type of lawyer or something
  20. Or somebody important or something?
  21. Nah I aint pass the bar but I know a little bit
  22. Enough that you won’t illegally search my shit.


In my rearview mirror is the motherfuckin law/I got two choices y’all, pull over the car or bounce on the double put the pedal to the floor.

According to Mason, “the calculation that 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.” The reality of situations like these is that it’s a personal decision based on the value of anything in the trunk, individual criminal background.

Mason believes that this is the hardest choice for people in the situation and concludes that there’s only one right 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.

It’s hard to disagree with Mason here because running from the police provides the police with an independent basis for chasing and arresting you. In short, if the police didn’t have a good or “legal” reason for stopping you before you fled, in fleeing from them you’ve just given them all the reason that they need to arrest you and legal seize the contents of your vehicle as evidence in your prosecution. Mason’s analysis here overlooks Jay Z’s assertion in Line 15 that “all his papers legit” because for some in the same or identical situation this may not be the case.

Mason stresses: “Smugglers, repeat after me: you have to eat the bust and fight it in court.” That’s fine advice if arrest, prosecution and seizure are the biggest concerns that the individual has. However, for some, if the contents of the trunk are illegal they will certainly be seized and whether the seizure was legal or not will not affect whether they can be recovered following a dismissal or not guilty finding.


And I heard, “Son do you know what I’m stopping you for?/“Cause I’m young and Im black and my hat’s real low?/Do I look like a mind reader sir, I don’t know/Am I under arrest or should I guess some mo’?

There are a lot of important things in these three lines. First, there is no constitutional problem for arresting someone for a traffic violation, no matter how minor. And, if you’ve been arrested your car can be impounded and searched to inventory its contents without a warrant. If you’re arrested, all of your belongings will be searched regardless of whether you’ve been suspected of anything. So, if you’re just being pulled over for a minor traffic violation but you’re otherwise up to something and you don’t want your car to be searched, we recommend being polite as possible and cooperating where you can so that you can go on your way. If you’re asked whether “you know why/what you’re being stopped for” just say that you don’t know and that as soon as you saw the lights in the mirror you asked yourself the same question.

However, the police cannot legally search your car unless you’re under arrest unless they have probable cause or you give them permission. If the police ask whether they can search your car you should politely decline. You don’t have to provide a reason but the truth is that unless you’ve maintained complete and total control over the car you’re operating you can’t possibly know what’s inside.

If you haven’t been arrested and the police search your car without your permission the search and anything recovered in that search will be subject to suppression. That’s all well and good. But it’s really important to remember two things: 1) neither you nor your lawyer can control whether the cops will give truthful testimony; 2) if you were illegally arrested and the powder cocaine seized form your trunk determined to have been illegally seized by a judge, you’re not getting your cocaine back.

It’s important to have some sort of proof that you never gave permission if there was no probable cause. The best advice Tower Legal offers in this point is to contact an attorney, preferably us, so that any evidence law enforcement might have such as dash cam or other footage can be preserved for hearing or trial.


“Do you mind if I look around the car a little bit?”/“Well, my glove compartment is locked and so is the trunk in the back,/and I know my rights so you go’n need a warrant for that:

Here Mason is at his best, “If this Essay series no other purpose, I hope it serves to debunk, for any readers who persists in believing it, the myth that locking your trunk will keep the cops from searching it.” There is no warrant requirement for car searches. Let’s say that again, there’s no warrant requirement for car searches.



Mason continues, “You don’t have to arrest the person, or impound the vehicle. You just need probable cause to believe that the car contains evidence of crime. So, in any vehicle stop, the officers may search the entire car, without consent, if they develop probable cause to believe that car contains, say, drugs.”All the action, in short, is about probable cause. Warrants never come into the picture. The fact that the trunk and glove compartments are locked is completely irrelevant. Now, Jay-Z may have just altered the lyrics for dramatic effect, but that would be unfortunate insofar as the song is going to reach many more people than any criminal procedure lecture, and everyone should really know the outline of the law in this area. What the line should say is: “You’ll need some p.c. for that.” Given that we’ve established (it appears) that Jay-Z is not under arrest, and given that the Terry frisk of the car is limited to accessible places a weapon could be hidden, the trunk is definitely off limits at this point. What that means is that if the officer opened the trunk by force, without developing articulable probable cause, the contraband found inside would be suppressed. That is the point of the next line.”


Check back to the Tower Legal blog for updates on this post and other Fourth Amendment posts. Nothing in this post is meant to constitute legal advice. If you’d like legal advice, feel free to contact Tower Legal at 312-619-3536 or info@towerjustice.com

Tower Legal is Chicago’s premier Criminal Defense firm with seasoned attorneys specializing in Fourth Amendment and narcotics defense cases.