The Bleak Truth Behind My ‘Inspiring’ Path From Oakland to Yale

When I decided to attend Yale five years ago, people held me up as an example of a black student who “beat the odds.” I wish they were more curious about why my brother wound up in prison instead.

An illustration of two men's profiles, back to back.

The day after my 18th birthday, I boarded a plane and left Oakland for Los Angeles, where I was to announce on national TV which university I planned to attend in the fall. It was April 22, 2014. The 45-minute flight was quick, and before I knew it, I was in the green room. Everybody was so kind; the atmosphere was cheerful. I waited backstage for my introduction.

“Despite living in the inner city, our next guest has made his own path to success, earning a 5.0 GPA and scoring a 2100 on his SATs. He has been accepted into many Ivy League schools and proves that, with hard work and support from family, anything is possible. From Oakland, California, please welcome 18-year-old Tunde Ahmad,” Ellen DeGeneres proclaimed.

I gave Ellen a hug as I settled into the guest chair and started talking about how I’d learned to dance. I then shared a few details about my life and the steps I’d taken so that I—a kid from 98th Avenue, in East Oakland—could reach this privileged moment. I did my best to give a vivid sense not only of my years of hard work, but also of Oakland, the city I loved so much. With my parents beaming in the audience, I announced to the world that I'd be spending the next four years as a Bulldog; I was going to Yale. As Ellen began to talk about how expensive college would be, a man appeared onstage with a giant cardboard check from Shutterfly and gave me $15,000 to help me pay for school.

Throughout my life, family, friends, and community members have rooted for me. But in this particular moment, my mind was focused on just one person: my older brother, Azeem, who was at FCI Herlong, a federal prison, where, the next day, when the Ellen episode aired, I thought that he and his friends there would be celebrating me, their “lil homie.”

Ellen and I discussed how my brother had been shot during my junior year in high school. We quickly returned to positive conversation, not mentioning that right then, as I sat there on that stage, he was incarcerated. It was as though his life was a footnote in mine. But that’s not the case at all: In the five years since, I’ve realized that the significance of our story lies in our diametric outcomes, understood together.

For my brother, the day that Ellen episode aired was no celebration. In a reflection he wrote the year after his release and later sent to me, Azeem described his memories of the scene in the federal prison. “I felt myself holding back tears,” he wrote. “It was weird.” He continued:

Part of it came from how happy I was for little bro, but the other part was me reflecting on what I was going through. I was listening to Ellen interview him but I was also taking in my current situation. All the blacks were fixated on the screen, happy for me and patting me on the back; other racial groups looked on with hatred because they realized that it was my little brother when a picture of the two of us appeared on the screen. It was probably the most bittersweet moment of my life. I’m locked down in a concrete refrigerator for human beings, being stored for years at a time in these khaki uniforms printed with shelving numbers. I’m only 22 years old, and I’ve been here for two years already, with nothing to do but read, work out, and wait to be released.

I know now that the media coverage of my rise from the Oakland Public School District to Yale was part of an annual tradition, when journalists write viral stories about high-school seniors from underrepresented backgrounds who gained admission to the nation’s most elite colleges, as one local reporter did about me.

In my case, the coverage focused on the juxtaposition of me and my brother, who was invoked as a stand-in for some stereotype of black men in America. How was it that he was incarcerated in federal prison, his body wounded by bullets fired from an AK-47, while I was choosing among top-tier universities?

In the comments sections below YouTube videos about me, the takeaway I most despised was thriving. "This is evidence that there is no such thing as systemic racism. Anybody willing to work hard enough can do anything in their lives,” one commenter wrote. “I wish more black people were like this guy,” another replied. To those who had this conclusion, I’m afraid you’ve missed the real story here, so let me try my best to tell it my way.

In 2012, during my sophomore year of high school, I got a call from my dad saying that my brother had been arrested. I was originally unclear about how and why he’d been taken into custody, but the Department of Justice later clarified: In a joint press release with the Oakland Police Department, it published the results of Operation Gideon III, a four-month effort to “target and remove violent offenders and to dismantle criminal organization and robbery crews operating in Oakland.” Its aim was “aggressively combating violent crime perpetrated by career criminals.” The operation resulted in the arrest of 60 suspects. My brother was one of them.

The operation was hailed as a success in the media; one headline read: “Operation Gideon III Nets 60 Arrests of the Worst Criminals.” According to the coverage, my brother was something of a career criminal. This made no sense. At the time, he was just 19 years old, had graduated high school, and was working six days a week, alternating between day shifts at the Enterprise car-rental office and night shifts at UPS. He was living at home and saving money to start his own business. He had no criminal record.

So what was he arrested for? Azeem and a friend fell for an “opportunity” to make some money, an offer by someone they later learned was an undercover agent. In Azeem’s telling, he and his friend weren’t sure of what the job would be, but they showed up to see whether it was something they’d be interested in. Once they arrived at the meeting and were asked to commit a robbery of a fictitious stash house, they got into Azeem's car to leave because, as he has always said, they didn’t want any part of it. They were arrested as they were leaving. Federal agents had been surveilling Azeem and his friends for months, via phone taps, hidden cameras, and undercover agents. All they needed to do was provide evidence that he’d ever had knowledge of other criminal acts, or had made verbal agreements to commit a crime himself, regardless of whether he’d followed through with it. Prosecutors claimed that he knew about the robbery in advance, though Azeem says he did not.

He was charged with multiple counts, including conspiracy to distribute cocaine, conspiracy to commit robbery affecting interstate commerce, and possession of a firearm in furtherance of a drug-trafficking crime. Ultimately, he pleaded guilty to the count of conspiracy to commit robbery, because like many individuals in our penal system, he feared the possibility of serving a long sentence if he lost his case at trial. He accepted a sentence of 41 months in exchange for this plea.

I was later informed that my phone had also been monitored because my brother and I were on the same phone plan. How easy would it have been for me to have said the wrong thing in a message, or to have been riding in the car with my brother when they arrested him, or to have had any other minor slip-up that could have landed me in juvenile hall or prison? America’s criminal-justice system catches kids like me on a daily basis.

Before my brother pleaded guilty, my family bailed him out on a house bond. That means we put a lien on our house through the court and signed an agreement that if my brother fled and didn’t attend his mandatory court dates, the state could take our property. Though this never came to pass, the prospect demonstrates the criminal-justice system’s potential detrimental effects on entire families’ economic stability.

On a Sunday in January 2013, while still out on bail, my brother asked me if I wanted to attend a family friend’s birthday party with him. I’d seen the friend the day before and had already wished her a happy birthday, so I decided to stay home and write an essay for my Advanced Placement U.S. History class instead. Around 7:30 p.m., I received a call that my brother had been shot when someone opened fire onto the porch where he and his friends were sitting. Five were wounded. Luckily, there were no fatalities. We still to this day do not understand what prompted the shooting.

The next month, his bail was revoked after failed drug tests, among other violations of his pretrial release agreement. Azeem had been out on bail for almost 10 months without having any bail-revoking infractions, and he says that the drugs he tested positive for were prescribed to him by his doctor as pain relief for his gunshot wounds. He was sent back to prison.

For black boys growing up in urban environments, staying out of the penal system is no easy task—not because we’re inherently troublesome, but because we are targeted by policies and tactics, such as Operation Gideon, that are meant to send us away. One mistake, and your entire life can be altered forever.

The fact is, my brother and I are far more similar than we are different. We are four years apart, but we grew up under the same roof, with the same two parents. We attended the same Oakland public schools, and played baseball and basketball on the same teams. Our parents instilled the same values in us, taught us both about the history of the black diaspora, and gave us both African names to reclaim our heritage and culture.

We are similarly intelligent, both academically and socially. Given the chance, Azeem would also have done well at Yale. Upon meeting us today, a stranger would have difficulty telling who had the Ivy League degrees (I later went to Columbia for graduate school) and who was formerly incarcerated. But for the rest of our lives, he will be stripped of certain privileges, while I will not. It isn’t because he was some monstrous person out to wreak havoc on the world. He was a 19-year-old kid, caught by a system designed to catch him. Since his release from prison, Azeem has become a dog breeder, and is now venturing into real estate.

People look at my story and applaud me and wonder what I did to “beat the odds.” I wish they were more curious about why my brother did not. I wish they would ask, “What trap lay before this talented, bright boy so that he was bound to fall into it?” I wish they would see how difficult it is to grow up a black man in America.

My story is told as though it is a positive one, inspirational. But I see it as a grim one, the tale of a harsh reality that wrecks people. There is nothing positive about classifying me as an exception. When a person is exceptional for doing what I have done, the whole system is cruel to its core.