99 Problems and This Bench Is One: Meek Mill's Decade-Long Battle - Aaron Delgado & Associates

99 Problems and This Bench Is One: Meek Mill's Decade-Long Battle

by Aaron Delgado
08/27/19 (Updated: 01/05/22)

Meek Mill, aka Robert Williams, a popular rapper hailing from Philadelphia, has spent the last decade dealings with bars, both lyrical and physical.  While many rappers seem to take inspiration from—if not pride in—their run-ins with the law, Meek's legal woes are uniquely epic. Meek's arduous journey through the criminal justice system has become a cause célèbre, uniting a diverse assortment of celebrities and activists from all walks of life in advocation for criminal justice reform.

Meek's supporters include fellow rappers such as billionaire entrepreneur and MC Jay-Z, professional athletes like the provocative Colin Kaepernick, and non-Grammy winning billionaire entrepreneurs Michael Rubin, Robert Kraft, and Daniel Loeb—who, inspired by Meek’s tumultuous legal experience, have all rallied to his cause. This star-studded super group led to the creation of REFORM Alliance, a criminal justice reform initiative that has already received over $50 million in pledges. For now, the initiative has its sights set primarily on the probation system—the mechanism through which Meek Mill was trapped in the criminal justice system for over a decade, because of a mistake he made as a teenager. To understand why Meek Mill has become such a symbol for criminal justice reform, let's take a look back at the timeline of his experience in the justice system.

Meek Beginnings for a Young Rapper

This legal minefield that Meek has been navigating for over a decade all stems from an arrest when he was only 19 years old (he is currently 32). On January 23, 2007, a member of the Philadelphia Narcotics Field Unit (NFU), Reggie Graham, claimed that he saw Meek selling crack cocaine to an informant. The next day, the NFU obtained a warrant to search Meek’s home, and he was ultimately arrested as a result of the search and encounter.

Graham claimed that during the search, Meek had pointed a gun at him. Meek admitted to carrying a gun at the time for protection, but insists that he "ditched it" when he saw the police and never pointed it at them. Meek had also claimed that the officers used excessive force in the encounter, using his head as a battering ram to open a door, leaving his blood on the floor and ceiling. Meek was facing 19 charges when he went in front of Judge Genece Brinkley, who would go on to be a key player in Meek’s lengthy legal troubles. After Meek waived his right to a jury trial (reportedly to save legal costs), Judge Brinkley found him guilty of seven of the charges, and sentenced him to two years incarceration followed by eight years of probation.

The Arresting Officer & Possible Corruption

Reginald Graham—the officer who arrested Meek, wrote the search warrant, and testified as the sole prosecution witness at Meek’s trial—has since left the force and come under heavy fire for allegations of corruption.

In 2018, the Philadelphia District Attorney’s Office placed Graham on their “blacklist” of police officers who should not be summoned to testify as witnesses due to their questionable trustworthiness. This was likely (in part) because Graham had recently been the subject of a federal investigation into corrupt police conduct. Additionally, another officer who was at the scene of Meek’s 2007 arrest, Jerold Gibson, has written a sworn statement contradicting Graham’s account and claiming that Meek did not point a gun at them.

As of this writing, a Philadelphia judge has already dismissed three cases (unrelated to Meek) that hinged on Graham’s testimony.

From Early Release to a Biased Judge

Meek was released early for good behavior, began serving his eight-year probation sentence, and did well for several years until an encounter with police on Halloween in 2012. Meek was on his way to the airport when he was stopped by police, claiming they smelled marijuana in his car. Meek maintains he was arrested for refusing to allow the police to search his car. He was released the next day and charges were never filed.

Despite charges not being filed, Meek found himself before Judge Brinkley again. He had apparently tested positive for opiates in 2011, but was unable to have a hearing until this date due to being on tour. Judge Brinkley ordered two drug tests—there’s conflicting information regarding whether Meek tested clean or never took the tests, but either way Judge Brinkley prohibited Meek from touring until his next hearing. When she found out he had continued scheduling tour dates, the Judge ordered him to stay in the state until his next hearing. Touring is the primary source of income for many artists, so this prohibition significantly affected Meek’s career.

At his next hearing, in March 2013, Meek’s probation officer claimed the rapper violated the travel restrictions of his probation. Meek argued that his schedule is incredibly hectic and can change quickly, asking for leniency. He claimed that it was simply a matter of needing to change his approved travel plans last minute when Hurricane Sandy struck New York. Judge Brinkley nonetheless found Meek in violation of his probation and refused his request to grant him a new probation officer. Additionally, because references Meek made on social media about his probation officer allegedly incited fans to send the officer death threats, Judge Brinkley ordered Meek to take etiquette courses as part of his probation.

In July 2014, Meek once again found himself in front of Judge Brinkley for a violation of probation hearing. The Judge sentenced Meek to three to six months in jail for failing to get her permission to travel for concerts. She also referenced a drug test where Meek tested positive for Percocet (which he began taking after having his wisdom teeth removed) and scolded him for negative tweets about his probation officer and being “combative” and “disrespectful” to probation staffers. As a result of this violation, Meek was in jail until December 2014 and was sentenced to an additional five years of probation.

In December 2015, Meek was in front of Judge Brinkley for a hearing on probation violation once again. It was alleged that Meek failed to report to his probation officer, disobeyed travel restrictions, and submitted cold water for a urine test. Brinkley prohibited Meek from traveling and performing until his sentencing hearing in February 2016. At the sentencing hearing, Judge Brinkley sentenced Meek to 90 days of house arrest and six more years of probation.

More Probation Time, More Problems

While serving this newly-lengthened term of probation, Meek had two more run-ins with the law. On March 15, 2017, Meek was charged with misdemeanor assault following an altercation in a St. Louis airport with an airport employee who tried to take a picture of Meek. On August 17, 2017, Meek joined some kids riding dirt bikes on the street in New York, and a video of him popping a wheelie was captured on his Instagram. The next day, the NYPD stopped him and arrested him for a felony charge of reckless endangerment.


Although all charges related to these incidents were ultimately dismissed, Judge Brinkley cited these arrests during Meek’s November 6, 2017, hearing for violation of probation. In addition to these arrests, she listed a failed drug test (supposedly for Percocet) and failure to comply with an order restricting his travel as additional reasons for the violation. She sentenced Meek to two to four years in prison for violating the terms of his probation. Notably, both the prosecutors and Meek’s probation officer were opposed to a sentence of incarceration, but the judge imposed one nonetheless. Meek’s legal team filed several motions to get him released on bail while they appealed the sentence, but Judge Brinkley denied the bail motion. She claimed that Meek “is and continues to be a danger to the community” and that he poses a significant flight risk, as the grounds for her denial of bail.

The Light at the End of the Tunnel

After years of being railroaded by the system in which he had become trapped, Meek finally secured a victory when, on April 24, 2018, the Supreme Court of Pennsylvania ordered the lower court to grant Meek unsecured bail immediately. This ruling seemed to be a shift in tides for Meek, as on July 24, 2019, he was finally able to overturn his conviction from 2008 and attain not only a new trial, but a new judge as well.

This was a momentous victory for Meek. Not only did he finally get a reversal on his 2008 conviction that was tainted by Graham’s questionable testimony, but he is now no longer under the thumb of Judge Brinkley, who seemed to ensure that he remained on probation for the past decade while showing a peculiar interest in his case. Her decisions themselves seem to suggest partiality, such as imprisoning Meek largely for technical probation violations against the wishes of the prosecutor and probation officer. But there are more direct claims of impropriety as well.

Meek’s attorneys claim that during a meeting in her chambers with Meek and then-girlfriend Nicki Minaj, Brinkley requested that Meek remake the Boys II Men song “On Bended Knee” and give her a shout out in the song. Brinkley even made a “surprise visit” to the homeless shelter where Meek was performing community service, which is highly unusual for a judge to do. Philadelphia District Attorney Larry Krasner even filed a brief with the Pennsylvania Supreme Court in May 2019 urging the high court to grant Meek a new trial and accusing Brinkley of demonstrating bias from the outset of Meek’s case. Mr. Krasner took particular issue with Brinkley’s visit to the homeless shelter and the way she relied upon her own observations to resolve factual disputes to revoke Meek’s probation.

After over a decade trapped in the criminal justice system, Meek Mill has finally received justice. Free from the scrutiny of Judge Brinkley, and with the questionable testimony of Graham no longer relied upon, Meek was given a fair shot this time around. On August 27, 2019—about a month after his original conviction was overturned—Meek plead guilty to a misdemeanor gun possession charge in exchange for all other charges being dismissed. Recognizing the injustice that Meek had suffered up to this point, District Attorney Larry Krasner accepted the plea, hoping it could help right this lengthy series of wrongs. As part of the deal, Meek will not serve any more time incarcerated or on probation. Now, at 32 years old, for essentially the first time in his adult life, Meek Mill is free. No more court dates, no more drug tests, no more check-ins with his probation officer, no more scrutinization of his every action. He is now able to travel where and when he pleases, to pick up his son from school, to live his life without the constant anxiety of probation hanging over his head. For the first time in over a decade, he is free.

Meek’s Case Brought Attention to the Criminal Justice Problem

Throughout this entire ordeal, Meek has spent an estimated $30 million dollars on legal defense. Most people don’t have that luxury, which is why Meek’s case has become so polarizing as a call for criminal justice reform. As Jay-Z put it in his op-ed with the New York Times, “What’s happening to Meek Mill is just one example of how our criminal justice system entraps and harasses hundreds of thousands of black people every day.” The fact that Meek went through all this despite his affluence further emphasizes how difficult it is to escape the system once it has you in its grasps. This highly publicized railroading of a young black man has forced many people to confront what happens behind prison and courtroom walls across the country every day.

It’s easy to bury your head in the sand and think that something like this could never happen to you. But Meek’s story paints such a vivid picture of how easily someone can get caught up and trapped in this vicious cycle, it forces people to confront these harsh realities. It also accentuates how unforgiving the system can be; a single mistake from your teen years has the potential to keep you trapped well into adulthood. In addition to highlighting the perils and pitfalls inherent in the criminal justice system, Meek’s story demonstrates the importance of navigating those perils with an experienced criminal defense attorney by your side.

Probation: The “Delayed Entry Program” to Prison

As experienced criminal defense attorneys, we know the dangers of probation—whether you’re Meek Mills or John Smith, probation can be a trap for the unwary. "Penitentiaries is packed with promise-makers" who made a promise to abide by the Department of Corrections' rules and regulations, only to fall short in some way—whether it was being outside of the county without permission, financial issues, or a new arrest (2Pac).

If you are considering pleaing to probation on a minor offense, you should ask your attorney about your alternatives—sometimes a weekend in jail now is way better than six months of probation and its accompanying risks.  Most lawyers think this, but how many are willing to tell their client the hard truth to do a short jail sentence and be done? We keep it as real as possible.

Your Criminal Defense Attorney Can Make All the Difference

Epilogue by Criminal Trial Lawyer Aaron Delgado:

At Aaron Delgado & Associates, we understand the role culture places in the justice system, for better or worse. Race and class are inescapable. It should be otherwise, but until it is, it is crucial to understand how culture can play a huge role in criminal defense work, from trial verdicts to sentencing.  We take the time to get to know our clients so that our knowledge is not just academic, but based on real experiences of our real clients.

As a fat, middle-aged white guy in a late model sedan, I do not get treated like my clients do. I have not grown up in a culture where casual racism is common place. I have learned how that affects clients and juries, and I think it has made me a better lawyer.  At Aaron Delgado & Associates, we are real people representing real people, many of whom become our friends. We are proud to be part of our community and to be champions of people, regardless of race or creed. If you or someone you know needs legal representation because they have been arrested injured or wronged, give us a call 24/7.

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