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After Earning $91M in the NFL, DeSean Jackson Has a $1B Blueprint in Magic Johnson
Welcome to Gridiron Wallet — where NFL players don’t just chase rings, they chase bags. From million-dollar grills to side hustles that slap, we’re decoding how football’s finest make it, spend it, and sometimes… fumble it. 🏈🔥
The latest edition of our newsletter covers DeSean Jackson:
DeSean Jackson’s Billionaire Blueprint
DeSean’s Early Steps: Coaching, Real Estate, and Media
What Comes Next? Ownership and Strategic Equity
✍️Paper Play
DeSean Jackson’s Billionaire Blueprint
DeSean Jackson retired from the NFL three years ago after an illustrious 15-year career that included three Pro Bowl nods and 11,263 receiving yards. But he wants his second act to be even bigger than his first.
Jackson wants a billion-dollar empire like the one that Los Angeles Lakers legend Magic Johnson has built. “I’m not playing for just millions anymore. I’m aiming for a billion-dollar portfolio,” he said, per Andrew Petcash.
The wideout did pretty well for himself in the league, making $91 million over his decade and a half of service. But that money is not nearly enough to satisfy Jackson.
As early as 2023, right after he retired, the speedster said that he wanted to get on “some Magic Johnson-type sh*t” while appearing on the No Jumper podcast.
“The hustler I am, I ain't satisfied with the money I made in the NFL. I would meet you today, and you wouldn't even think I made 100-plus million in [the] NFL,” Jackson had said.
“Because guess what? That money right there, that's going to make my future cool for my kids. But right now, I still need bread, so I'm out here getting all types of stuff, going private equity, real estate ... Sh*t, f**k the NFL. That sh*t was cool, but what's next? I'm trying to go touch some Magic Johnson-type sh*t,” he added.
Right there, he already mentioned a few of the things he had begun to dabble in to start building on the near-$100 million he made as a pro athlete. But the most important — and the first — thing he did was hire his mother, Gayle Jackson, to advise and guide him in this ambitious financial journey.
“She cares for me, doesn’t really trust anybody, and understands money. So she’s very familiar with contracts and numbers,” said Jackson, who has his mother at his side and has Magic Johnson’s off-court career as a guide.
That’s a pretty good start. Johnson has invested in many products, companies, and services over the years. Some of his largest, most well-known investments include the MLB’s Los Angeles Dodgers and the NFL’s Washington Commanders. He has also invested in Starbucks and real estate. So there’s the blueprint.
Jackson was an all-or-nothing, boom-or-bust player. And he was ‘boom’ a lot more than ‘bust’. He is perhaps the greatest deep threat of all time. His 17.6 career yards per reception mark sits first among WRs with 500+ receptions since 1980. He was all about big-risk, big-reward plays.
But he is a picture of contrast in his second career as a businessman.
Jackson has already started building his empire with smart and safe moves. He created his podcast, Fade The Booth, which is a low-cost endeavor with high potential. He’s been an angel investor in Betr and Fanatics, two fast-growing businesses.
Jackson has also already invested $35 million in a large portfolio of real estate holdings, following Johnson’s footsteps. And he founded a holding company, J&D Investments Ventures, to help him navigate everything.
And in between all of this, Jackson is also going into his debut season as a head coach. His first coaching job has taken him to Delaware State in the MEAC for the upcoming 2025 campaign. He indeed is attempting to have it all.
💸Bit by Bit
DeSean’s Early Steps: Coaching, Real Estate, and Media
DeSean Jackson, who seems to be following in the footsteps of Deion Sanders, was recently announced as the new head coach of Delaware State University. It’s the former NFL wideout’s first coaching job after serving as the offensive coordinator for Woodrow Wilson High School in Long Beach, California.
Jackson was hired to get Delaware State back to winning ways. They’ve gone 2-21 over the past few seasons. However, they are a program that has won nine conference championships, including six in the MEAC from 1985-2007. They’re currently in Division 1 FCS, just a step below the FBS.
Ever since retiring, Jackson has also started investing in real estate in areas like Los Angeles and Long Beach, where he grew up. He owns properties ranging from commercial to residential, and flips them for good profit.
Jackson is especially focused on purchasing and redeveloping affordable housing, inspired by how Magic Johnson redeveloped black neighborhoods in LA. Additionally, similar to Deion, his insertion into the Delaware State community could do wonders for them financially. Whether it’s a nationally televised game or an increase in attendance, Jackson will surely attract attention.
In addition to coaching and real estate advancements, Jackson has also quietly started advancing in the film and digital content space. He greenlit a documentary on himself in 2023. He has also partnered with various brands since retiring, including Pineapple Wellness.
Jackson even hinted at a podcast in the works. He starred alongside his former teammate LeSean McCoy for about a year in their podcast, The 25 10 Show. But it never took off, and the two stopped when McCoy became a host with The Facility. Now, he’s looking for a show that sticks.
Regardless, through media ventures, along with the real estate advancements, Jackson has managed to stay financially prosperous even after his playing career. It’s something we’re seeing more and more nowadays after players retire. The modern-day media landscape allows it to happen.
But Jackson doesn’t want to be just another retired player in the media. He wants to be like Deion and Magic in the space, and build an empire off the field while giving back in the process. It’s an admirable ambition for a player who was a fan favorite during his playing days.
💡 Gridiron Wallet Trivia
Did you know?
🌿 DeSean Jackson once bought a custom $250,000 bulletproof Maybach. Early in his NFL career, he had the luxury car armored for safety—reportedly inspired by his upbringing in South Central L.A.
It wasn’t just flashy—it was tactical. Jackson spent big, but always with a reason, blending street smarts with star power.
🏈✨Eggs In All Baskets
What Comes Next? Ownership and Strategic Equity
Based on his NFL career and multiple investments listed so far, it’s evident that DeSean Jackson is not the kind to rest on his laurels. This is why, even after earning $91 million during his NFL career, plus millions more from endorsements, Jackson has transitioned from elite wide receiver to a determined investor, entrepreneur, and media figure.
But now, as he edges closer to the $100 million net worth mark, the question is, what’s next for the three-time Pro Bowler? While there is no clear answer to this question, it looks like he is eyeing his boldest moves yet. It involves sports ownership and long-term strategic equity plays.
Though he hasn’t publicly confirmed specific negotiations, Jackson has openly expressed admiration for Magic Johnson’s business blueprint — one built on minority ownership stakes in marquee franchises, including the Los Angeles Dodgers, Washington Commanders, and ventures like Starbucks.
Given that, it's reasonable to anticipate that Jackson may explore ownership stakes in major sports franchises. As of now, NBA or MLS teams appear to be likely targets, especially since these leagues have, of late, been the investment haven for ownership groups, including athletes, celebrities, and private equity firms.
Similarly, while no specific deals have been announced, Jackson’s business pattern, investing through J&D Investment Ventures, Fanatics, and in real estate, suggests a continued focus on scalable, long-term opportunities.
Considering this, it’s fair to expect him to pursue ventures such as health brands serving underserved communities, entertainment projects centered around urban storytelling, or tech platforms that bridge access gaps. These areas also align with his Magic-inspired generational wealth strategy.
But unlike many athletes-turned-investors, Jackson is approaching this phase with notable restraint. So far, he has kept his ventures largely private, avoiding the media blitz that often accompanies celebrity investments.
Rather than appearing on podcasts and at business meets and sharing his investment stories, Jackson has meekly gotten into coaching at Delaware State while silently making his business moves.
This quiet approach intriguingly mirrors the early years of Magic’s off-field empire, filled with calculated moves behind the scenes that focused on results over headlines.
And last but not least, on the philanthropic front, he continues to channel his efforts through the DeSean Jackson Foundation, inspired by his mother, Gayle, and aimed at battling pancreatic cancer and supporting youth programs.
Jackson is prioritizing patience and precision, putting himself in a position to make an impact in the next decade. And rightly so, because he’s chasing equity — the kind that endures.
📆 NFL Money Stat of 1970
The average NFL salary in 1970 was just $23,000—less than the average American household income at the time.
Many players had offseason jobs to make ends meet—working as teachers, salesmen, even bartenders.
By contrast, today’s NFL minimum salary is $795,000, and some kickers earn more in one game than stars from the 70s made in an entire season.