Whether or not a person can hang their metaphorical jersey in the rafters or their surname only succumbs to a headstone in the graveyard, the timestamp of their stay is bolded for everyone to see.
You win some, you lose some, but you can try again next time. There’s always a next time—always seconds—second tries, second chances, and second guesses because every redo is unlike the original. The definition of winning is more than the outcome. I have won, even in defeat.
Our professional wins and losses are recorded on résumés, CVs, and portfolios. Oh, how funny that we emphasize what we want others to perceive about us in these professional documents. Even more amusing, removing the accent marks from the “e,” the word “résumé” becomes “resume,” which is what our lives and the world around us will do anyway.
Growing up, a career was considered a permanent calling, so naturally, I wouldn’t consider a second career if my first was meant to be my vocation. Some kids didn’t have a choice in their calling, doing what they had to do to give their families a better future, but that doesn’t mean the calling wasn’t for them.
“At the age of 11, you know, 12, 13, basketball became a job,” said retired NBA veteran, Brandon Jennings.
Second chances aren’t the same as new beginnings. Resurgence is similar, but the act is incumbent upon the person. When I consider the fate of my future, I know new beginnings will be on my horizon, second chances will be scarce, and resurgence will take place when I’m good and ready. These edicts are cherished because they temporarily discard my past.
Depending on historical impact, it’s exciting when a trend from the past resurfaces. Folks who experienced the original iteration quickly let the youngsters know it was theirs to witness first. Yet, there is still an eagerness to indulge in resurgence.
In 2008, hip-hop duo The Cool Kids released their debut album The Bake Sale, highlighted by the now cult classic single “Black Mags.” The sounds of big bassy rhythmic tones accompany a black and white music video. The song immediately hits the listener with nostalgia, when nostalgia was widely crafted into how we know it today. The music video shows the Midwest hip-hop duo sporting vintage pieces from the late ’80s and early ’90s. In the opening verse, rapper Chuck Inglish brags, “I got this ’89-’90, Pistons champ flat/Bill black Starter cap with the hologram tags.” The song is riddled with flexes to their procurement of nostalgic flyness as it relates to BMX riding, which was gaining popularity in its own right around this time. The Cool Kids weren’t the only hip-hop group giving off this penchant as Kid ’n Play imitators.1 There was a niche camp of hip-hop artists bringing back hip-hop's golden age, and it was very infectious for a brief moment in time. I remember my high-school friends wearing the likes of Reebok Pumps, Starter snapbacks, and neon-colored windbreakers to prove our affinity to the subculture. We couldn’t afford Cazal frames so we sported the other tell-tale sign of an early 90s hip-hop appreciator – the hi-top fade.
The second pass of clippers gliding over coiled curls completes the clean look for a hi-top fade, or flat top, as some people call it.
Each of us grew our hair for a hi-top fade and a chance at getting closer to the heaven of heavens. Brandon Jennings came even closer as I witnessed his hi-top come inches to kissing the rim from a windmill attempt. The Gardena, CA native could easily windmill and tomahawk standing at just 6’1”, a small guard by NBA standards.
Jennings attended Oak Hill Academy, a prep school basketball powerhouse. By the end of his senior year, he averaged 35.5 points and 6.4 assists per game, scored a single-game school record of 63 points, and was named Naismith High School Basketball Player of the Year. He capped off his stellar high school career by starting in the 2008 McDonald's All-American game in Milwaukee, WI.
Many future NBA players took the court in the 31st annual rendition of the game. Demar DeRozan, Kemba Walker, and Jrue Holiday became Burger Boys the same year, but all eyes were on Jennings. Viewers couldn’t deny the star power he showcased during the game, and star power is something you can’t quantify. It wasn’t the number of points he scored (12); it was how he scored them; it wasn’t how many assists he recorded (9); it was how the assists gradually became flashier with each second passed.
Jennings showcased energy and passion for the game, mimicking the tenacity of former LA resident who once donned purple and gold.
After that game, the kid with the loose-fitting jersey and the hi-top fade solidified his legendary prep career. During the game’s telecast, a graphic showed where all the top players were heading to college. Many of the players shown committed to some of the top schools in the nation, but it was hard not to notice Jennings’ commitment to Arizona. It was a flip from his original verbal commitment and resident university, USC. Ultimately poor SAT scores halted his college hoop dreams.
Pivot /ˈpivət/: A pivot is when a player stands still and steps with one foot. The foot that stays on the ground is called the pivot foot.
His next decision would change the pipeline to the NBA forever. Foregoing his NCAA eligibility, Jennings became the first American player to skip college to play professionally overseas. At just 19 years old, he began his career.
Career consumes us, as we often spend more time working than at home. Our careers are tethered to our being, with the immense pressure to abide by the occupational rules or fail. There’s a eureka moment when we recognize the tether connecting our identity and career. We go from dreaming our wildest dreams to shaping them into reality as best we can. Before a person comprehends their fear of heights, they dream of flying.
After his stint overseas, Jennings would be drafted by the same team that called the Bradley Center home, a second chance to flash his greatness in the city of Milwaukee. It wasn’t just the explosiveness, left-handedness, and quickness that drew me to Jennings’ style of play, which is similar to AI; it was his aura. So, cousins, you must excuse me when I tell you that I thought the young point guard who wore No. 3 for the Milwaukee Bucks in 2009 was the second coming of The Answer.
On November 14, 2009, rookie Brandon Jennings exploded for 55 points against Stephen Curry’s Warriors, setting an NBA record as the youngest person to score 50 points in a game. Bleacher Report journalist Dwayne Montell wrote:
“Like his favorite player, Allen Iverson, he is extremely quick and fearless, though he has a better shot than AI did in his rookie season. The Bucks have themselves a franchise player and he is already proving to be one of the best point guards in the league.”
Jennings didn’t become the franchise player we all hoped for. In a few short years, he became the second option to a 19-year-old athletic freak from Greece. Then the flashy guard was traded to the Detroit Pistons.
On January 15, 2015, at the Bradley Center, Jennings returned to face his former team. Going into the game, he had a productive year, showcasing career highs in Field Goal percentage and Free Throws. His matchup for the night was Brandon Knight, who was a part of the trade deal that sent Jennings to Detroit. Late in the 3rd quarter, with the Pistons down by 14 points, Jennings pressed Knight before a Jared Dudley inbound pass. As Knight pushed off Jennings to free himself up for the pass, Jennings fell to the hardwood in pursuit. If you didn’t know any better, you’d think Brandon on Brandon crime occurred the way Jennings went down in pain, unfortunately, he tore his achilles tendon, ending his season.
It was during his time in recovery when Jennings lost his passion for the game. Jennings had to come to terms with the relationships around him and being laid up in the bed meant he couldn’t evade the off-the-court chaos that would catch up to him.
“I needed that time to sit down and realize who I am,” Jennings told All The Smoke podcast hosts, Matt Barnes and Stephen Jackson.
After his surgery, he made a few stops around the league but ultimately ended up back where he started, playing overseas. While playing for the Brave Dragons in China, he was inspired to begin his second career as an entrepreneur and fashion designer for his clothing brand named, Tuff Crowd.
“There’s different opportunities, different things that we might not know we’re really good at until we really just take a risk,” Jennings asserted. “Take a chance at it.”
The road to recovery is tough, and the clothing brand's name coexists with Jennings’ outlook on life from that point forward. There will always be a tough crowd, a “them” who is against “us” to critique the uncertainties of life’s timeline. The clothing brand was a fresh start.
A clean slate provides comfort in the company of my procrastination. The daily demands surrounding the sentient road guarantee mistakes. Furthermore, rumination of the past pushes my mind to fatigue. Fresh starts allow for reprieve.
As it concerns our questionable affairs, I’d love to tell you that good balance is achievable, but to be frank, they are either balanced or imbalanced. Maybe you’ve heard of work/life balance, but that doesn’t exist; it's just life balance, which is still questionable sometimes. So, I spew answers while looking for the correct solution.
Jennings is also a co-host on Gil’s Arena, a podcast about basketball hosted by NBA veteran Gilbert Arenas. Like most podcasts, the goal is to discuss the current news cycle and provide outrageous takes that are more about spiking ratings than sincerity.
While on Gil’s Arena podcast, Jennings claimed Jayson Tatum was the “softest Boston Celtics superstar ever.” His co-hosts pressed him about the take as he continued to double down, spewing answers, even mentioning Tatum not being among the top 5 Boston Celtics players ever. Brandon Jennings became the tough crowd/Tuff Crowd.
Doubling down also gives us a second chance. When a person doubles down on their original answer, whether helpful or hurtful, pride comes into play. Doubling down is a second chance where we are completely in control of our offenses, but so is walking things back, possibly allowing us to retract from the very thing we despise.
Providing a second answer doesn’t promise we’ve found a solution. Problem-solving is similar but the act is incumbent upon the person, sending them down a different path. The issues of the world help keep me in check. I search and search, chronically online, until many results quickly come across my screen. Thankfully, I still get my questions answered by the elders around me. The only difference is that their answers come back slower and without hyperlinks. Nevertheless, the sincerity in their vocal comeback makes up for the lack of haste, as they conjure up their past experiences to impart wisdom.
Brandon Jennings was included in Oak Hill Academy’s second Hall of Fame class. During his induction speech, a visibly emotional Jennings sent a message to the current basketball team, reminding them to be grateful because eventually, things come full circle.
He designed the Hall of Fame jackets worn by the new class, which are complimentary of his brand Tuff Crowd. Full circle, indeed.
©Cole Henderson. All Rights Reserved.
I believe this hip-hop subculture was the launching pad to the Cali Jerkin’ movement a few years later.
Bro, you’re such a beautiful writer. It really feels like I’m playing ball when I’m reading. You really know how to shift between the story, stats, and song of a piece. Keep going.
Loved this piece! You're one of the few writers that really captures the magic of having a favorite player and watching them be in the moment.
If you haven't already, I would recommend watching some episodes of the 'Pivot' podcast because it usually has a segment where the guest talks about when they had to turn things around and take that second chance at life.
Carmelo Anthony's '7pm In Brooklyn' is similar in that regard but it's more about moments when people had to lock in and take charge of their life / careers