• Loading stock data...
Monday, September 15, 2025
One Day till Tuned In! Get a Last Second Ticket!

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

Trump Push to End Quarterly Earnings Has Major Sports Ramifications

U.S. President Trump proposes moving to semi-annual reporting for public companies.

Warriors $75M Pitch Fails to Sway Kuminga As Season Looms

Kuminga and his representatives want a long-term deal.
Sep 11, 2025; Minneapolis, Minnesota, USA; Minnesota Lynx forward Napheesa Collier (24) dribbles past Golden State Valkyries forward Janelle Salaun (13) in the second half at Target Center.

As WNBA Grows, Engelbert Says Its Playoff Field Won’t for a While

Eight of thirteen WNBA teams made the playoffs this year.
Sep 10, 2025; Uncasville, Connecticut, USA; Connecticut Sun forward Aaliyah Edwards (8) fights to keep the ball in-bounds during the second half against the Atlanta Dream at Mohegan Sun Arena.

Connecticut AG Demands Documents From WNBA About Sun Sale Process

The WNBA reportedly prefers to move the team to Houston.

Featured Today

PHILADELPHIA, PENNSYLVANIA - APRIL 19: A detailed view of the MLB Debut patch on the jersey of Patrick Monteverde #44 of the Miami Marlins prior to game against the Philadelphia Phillies at Citizens Bank Park on April 19, 2025 in Philadelphia, Pennsylvania.

The Tiny Jersey Patch at the Center of the MLB Rookie Card..

Autographed cards containing a piece of baseball history have upended the market.
September 11, 2025

Eagles-Chiefs Super Bowl Rematch Could Set More NFL Ratings Records

Fox will nationally televise Sunday afternoon’s matchup.
September 10, 2025

ESPN’s ‘MNF’ Ratings Up 8% As NFL Surges to Strong Start

ESPN posts its second-best Week 1 “Monday Night Football” audience.
Sep 7, 2025; Orchard Park, New York, USA; Buffalo Bills fans react during the fourth quarter against the Baltimore Ravens at Highmark Stadium.
September 9, 2025

As Bills Ascend, Their Next Frontier Lies in Canada

Buffalo and the powerful Canadian entity MLSE come together in a new pact.
Joe Burrow

Joe Burrow Out for Months After Bengals’ Pricey Offseason

Tee Higgins and Ja’Marr Chase are the highest-paid WR duo in NFL history.
September 10, 2025

Kuminga, Grimes Remain Unsigned As Giddey Agrees to $100M Deal

Two of the four restricted free agents have inked deals.
September 11, 2025

NHL To Allow Players From Hockey Canada Trial To Return This Winter

The five Canadian players were all acquitted in July.
Sponsored

How World Series Champ Dexter Fowler Became a Premier League Team Owner

Dexter Fowler discusses navigating retirement and embracing new roles as an owner & investor.
September 8, 2025

Alcaraz and Sinner Have More to Gain in 2025 After Splitting Slams

Alcaraz and Sinner have split the last eight Grand Slams.
September 7, 2025

Alcaraz Beats Sinner, Wins $5M Prize, Reclaims World No. 1

Alcaraz won a record $5 million first prize at the US Open.
Angel Reese
September 5, 2025

Angel Reese Suspended For Half-Game After Ripping Teammates

The team is disciplining Reese for criticizing her teammates publicly.
Caitlin Clark
September 4, 2025

Caitlin Clark Says She Won’t Return From Injury This Year

She only played 13 games this season.