• Loading stock data...
Saturday, February 14, 2026

Gradey Dick Wants Drake’s Help With Managing His Money

  • Toronto Raptors first-round pick Gradey Dick learned about taxes at the NBA Rookie Transition Program in Las Vegas.
  • NIL helped Dick learn the “background of a business” while at Kansas, where he had deals with Adidas, Beats by Dre.
Toronto Raptors first-round pick Gradey Dick learned about taxes at the NBA Rookie Transition Program in Las Vegas.
Mandatory Credit: Wendell Cruz-USA TODAY Sports

After being selected 13th overall by the Toronto Raptors in last month’s NBA Draft, former Kansas sharp-shooter Gradey Dick got a DM reading “welcome home” from Drake, the rap icon and world’s most famous Raptors fan.

“He’s on tour right now, so I haven’t got to place a face, but when [Drake’s] back, we might meet up and just talk for the first time,” Dick, who was recently in Las Vegas for the NBA Summer League, told Front Office Sports. “I’m excited to meet him and pick [his] brain. He has a background with all this financial stuff.” 

Drake — who, per Forbes, earned an estimated $49 million in 2020 alone — became a global ambassador for the Raptors in 2013, and his record label OVO acquired naming rights to the team’s practice facility in 2019. The Kentucky men’s basketball team recently practiced on Drake’s $100 million Toronto home gym, and his other sports interests span OVO’s FC Barcelona apparel collaboration and his investments in Italian soccer club AC Milan and Overtime’s OTE basketball league.

For now, Dick, who signed a four-year, $21.4 million rookie deal with the Raptors, is leaning on the NBA’s Rookie Transition Program that was held across four days in Las Vegas. New Orleans Pelicans forward Larry Nance Jr., who recently bought an ownership stake in English soccer club Leeds United, was among the veterans to talk to rookies in Vegas.

“Larry Nance talked a lot about being smart with money, the things people don’t think about with taxes and different locations where they take a large sum of it away where guys may not be thinking about that when they get their paycheck and are surprised by the number that actually comes through,” Dick said. “Me personally, I’m a big saver, so it was helpful hearing from [Nance] how he keeps track of his money.”

As an American in Canada, Dick and his teammates who claim U.S. residence will not only be federally taxed by the IRS on all income but are also likely taxed Canada’s maximum 53.53% rate (combined federal and provincial) for all game checks on Raptors home games. When the Raptors played home games in Tampa for the 2020-21 season due to the pandemic, players saved millions of dollars in taxes by playing in Florida, a state with no income tax.

“One of the things I had to understand quickly was the different tax rules. I’m honestly still learning about it,” said Dick, who is repped by WME Sports.

At Kansas, Dick had NIL deals with Beats by Dre, Addias, apparel brand Charlie Hustle, Tommy’s Express Car Wash, and Continental Tire. Now as a pro, Dick has re-upped with Adidas and partnered with Chipotle and Philips Norelco. The 19-year-old Wichita native credits NIL for giving him a head-start on business savviness.

“The stuff I was able to learn with NIL throughout college—not only just doing cool commercials but learning the background of a business and how to take care of money at an early age—I was able to carry that on to some of these discussions out here [in the NBA].”

The Rookie Transition Program is led by Jamila Wideman, the NBA’s SVP of Player Development. She also is an original WNBA player, having played in the league’s inaugural 1997 season through 2000.

“I think NIL is a really good example of a recent advent that we’ve had to pivot around very quickly,” Wideman told FOS. “What it really reveals is that the starting point for when players should have access to resources to manage and understand their finances is now starting a little bit earlier. The silver lining of that is that some of the guys coming in have had that in variance and are coming in with some level of awareness.”

A college player’s NIL experience can vary greatly depending on their sport, school, conference and individual success. For basketball and football players at Power 5 schools, the top-half earners averaged $45,000 in NIL deal profits, while the bottom half averaged $15,000 annually. Former University of Michigan basketball star Hunter Dickinson said this spring that his decision to transfer to Kansas, Dick’s alma mater, was driven by NIL opportunities.

“It’s also an area where we wanna be very careful not to paint with a broad brush,” Wideman said. “Because where one guy who has an NIL deal might have had a tremendous amount of resources and education around how to manage that deal, another guy may not have. And so when we meet with them at the Rookie Transition Program, we’re learning who is who.” 

Former NBA players Eddy Curry and Tracy Murray also spoke at the Rookie Transition Program, as well as Hall of Famer Ray Allen.

“We try to tailor the resources and guidance we provide with an understanding of where guys are actually coming from. So we’re serving both individuals but also the collective of the guys, and we want to make sure everybody when they walk out the door, they share a baseline,” Wideman said. “Our programming really represents what’s happening in the wider sports world, what’s happening in the wider culture. Our programming is intended to evolve.”

The Rookie Transition Program also covers topics such as mental health, maintaining healthy relationships, social justice, sleep and nutrition, character building, and how to build a financial team. Also, after the NFL suspended nine players this offseason for league gambling policy violations, the NBA has spotlighted gambling education in Las Vegas. 

“[Sports betting] is an area that has suddenly become at the forefront, it’s certainly a conversation that we raise here at the Rookie Transition Program,” Wideman said. “There’s mandatory training related to gambling not only for rookies but for full teams. So making sure that players are absolutely aware of the rules, but also that they’re just aware of what the risks are more generally.”

Linkedin
Whatsapp
Copy Link
Link Copied
Link Copied

What to Read

Jan 28, 2026; Houston, Texas, USA; Houston Rockets forward Kevin Durant (7) shoots the ball as San Antonio Spurs forward Victor Wembanyama (1) defends during the first quarter at Toyota Center.

Critics Have Called NBA All-Star Game ‘Irredeemable.’ Can Wemby, Others Revive It?

Victor Wembayanama and Jamal Murray both said they will play hard.
Nov 29, 2025; Inglewood, California, USA; Los Angeles Clippers guard Chris Paul (3) brings the ball up court during the first quarter against the Dallas Mavericks at Intuit Dome.

Chris Paul Announces Sudden Retirement After Clippers Trade

Paul is fifth all time in NBA career earnings.
Jan 30, 2026; San Francisco, California, USA; Golden State Warriors guard Stephen Curry (30) reacts after a basket against the Detroit Pistons in the third quarter at the Chase Center.
exclusive

Curry’s Final Under Armour Sneaker Is Here. He Won’t Wear Them in..

Curry last wore Under Armour shoes on Nov. 18.
Nov 23, 2024; Salt Lake City, Utah, USA; Utah Jazz forward/center Lauri Markkanen (23) and Ryan Smith after a game against the New York Knicks at the Delta Center.

Jazz Owner Defends Team After $500,000 Tanking Fine From NBA

The Pacers were also fined $100,000 by the NBA.

Featured Today

Feb 11, 2026; Livigno, Italy; Jaelin Kauf of the United States during freestyle skiing women's moguls final during the Milano Cortina 2026 Olympic Winter Games at Livigno Aerials & Moguls Park

The Surprise Hit of the Winter Olympics: First-Person Drone Views

Tiny drone cameras have reshaped the Olympics viewing experience.
Feb 11, 2026; Milan, Italy; Madison Chock and Evan Bates of the United States skate during the Milano Cortina 2026 Olympic Winter Games at Milano Ice Skating Arena.
February 13, 2026

Olympic Figure Skaters Pay Out of Pocket for $9,000 Costumes

For four minutes on ice, stakes are high—and prices even higher.
February 11, 2026

Epstein Emails Show His F1 Ties Ran Deep

The sex trafficker’s circles included many of the biggest names in F1.
February 6, 2026

Milan’s Olympic Village Is Built for Performance—and Partying

Making Milan’s Olympic Village was a five-year sprint.

IOC Kicks Ukrainian Out of Olympic Race for Helmet Honoring War Dead

Vladyslav Heraskevych was disqualified Thursday morning.
Jan 17, 2025; Miami, FL, USA; Angel Reese (5) of the Rose takes a shot against the Vinyl in the first half of the Unrivaled women’s professional 3v3 basketball league at Wayfair Arena
February 11, 2026

Angel Reese Rejoins Unrivaled For Team’s Final Three Games

Reese will rejoin Rose BC to finish out the regular season.
February 11, 2026

LA28 Stands by Casey Wasserman After Reviewing Epstein Ties

Abby Wambach and Chappell Roan have left Wasserman this week.
Sponsored

Olympic Hockey Betting Preview: USA and Canada Take Center Ice

Olympic hockey betting odds shift as USA and Canada dominate early action, per BetMGM’s 2026 Winter Games preview.
Tennis legend Serena Williams, seen here waving to the crowd after losing the final match of her career to Ajla Tomljanovic 2022 U.S. Open tennis, has suffered two pulmonary embolisms — the first in 2011 and the second in 2017 after the birth of her first child. She was able to return to competition both times but has also said that she needs to be vigilant for the rest of her life when it comes to early detection of blood clots.
February 10, 2026

Serena Williams Eligible to Make Pro Tennis Return This Month

Williams originally stepped away from tennis in 2022.
February 8, 2026

Lindsey Vonn Breaks Leg at Olympics Days After Tearing ACL

Vonn tore her ACL on Jan. 30.
Feb 4, 2026; Milwaukee, Wisconsin, USA; Milwaukee Bucks forward Giannis Antetokounmpo (34) during warmups prior to the game against the New Orleans Pelicans at Fiserv Forum
February 6, 2026

Giannis Antetokounmpo Takes Kalshi Stake With Restrictions

The Bucks superstar is the first NBA pro to team with a prediction-market platform.
February 6, 2026

Dana White Says He’s No Longer Involved in Matchmaking, Contract Negotiations

Chief business officer Hunter Campbell handles the majority of negotiations.