• Loading stock data...
Thursday, December 18, 2025
Breakfast Ball is heading to San Francisco with hosts Joe Montana and Jerry Rice. Request to Attend

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

NBA Will Finally Decide on Expansion Next Year

Three team sales earlier this year halted years of expansion talks.

Adam Silver Says He Could Join WNBA CBA Negotiations

The commissioner says he’s “optimistic” the sides will reach a deal.
May 22, 2025; Oklahoma City, Oklahoma, USA; NBA commissioner is Adam Silver presents Oklahoma City Thunder guard Shai Gilgeous-Alexander (not pictured) with the Michael Jordan Trophy for winning the most valuable player award for the 2024-25 season before game two of the western conference finals for the 2025 NBA Playoffs at Paycom Center.

Adam Silver Praises Amazon NBA Coverage, With Subtle Jab at Others 

Silver praised Amazon’s coverage while taking veiled shots at league broadcast partners
Knicks

Knicks Won’t Hang NBA Cup Banner After All

The Lakers and Bucks both raised banners after winning the tournament.

Featured Today

How Pickleball Became One Massive Private-Equity Rollup

Pickleball roads lead back to billionaire Tom Dundon.
Dec 9, 2025; Toronto, Ontario, CAN; New York Knicks guard Jalen Brunson (11) dribbles against Toronto Raptors guard Jamal Shead (23) during the first half at the 2025-26 NBA Emirates Cup at Scotiabank Arena
December 13, 2025

The Lucrative NBA Cup Is Here to Stay

The in-season tournament, launched in 2023, is turning into a staple.
The Los Angeles Chargers host executives from UCLA Health on Wednesday, August 7, 2024 at The Bolt in El Segundo, CA.
December 7, 2025

The Multibillion-Dollar Business of Pro Athlete Recovery

What started as ice baths has evolved into a multibillion-dollar industry.
Big League Wiffle Ball
November 29, 2025

Celebrity-Backed Wiffle Ball Has Big-League Aspirations

Big League Wiffle Ball team owners include Kevin Costner and David Adelman.
Dec 7, 2025; Glendale, Arizona, USA; Los Angeles Rams wide receiver Puka Nacua (12) reacts after scoring a touchdown against the Arizona Cardinals at State Farm Stadium.

Puka Nacua ‘Deeply’ Apologizes for ‘Covetous Jew’ Dance

The Rams star appeared on a livestream with Adin Ross and N3on earlier this week.
Aug 27, 2025; Flushing, NY, USA; Polina Kudermetova of Russia in action against Aryna Sabalenka of Belarus in the second round of the women’s singles at the US Open at Arthur Ashe Stadium in Billie Jean King National Tennis Center.
December 15, 2025

Three Russian Tennis Players Have Switched Nationalities in Offseason

Aryna Sabalenka has said she plans to continue to represent Belarus.
Allisha Grat
December 18, 2025

WNBA Players Authorize Strike in Near-Unanimous Vote

93% of players voted and 98% of them voted yes.
Sponsored

Brian Hoyer: Patriots Lessons, NIL Chaos & His Post-NFL Career

The former Patriots QB talks to FOS about college football’s radical transformation.
December 15, 2025

Philip Rivers Return Means 5 More Years of Health Insurance—for 10 Kids

The QB’s large family can get another half-decade of health coverage.
December 12, 2025

Caitlin Clark Says She’s ‘100%’ in Return to Court at USA Camp

Caitlin Clark returned to the court at full strength for USA Basketball.
Tennis
December 11, 2025

Tennis Pro Suspended 20 Years for Alleged Match-Fixing Syndicate

Quentin Folliot was also fined $70,000.
Trinity Rodman
December 11, 2025

NWSL Will Vote on Seismic Rule Change to Keep Stars Like Rodman

The battle over Trinity Rodman’s future could reshape the NWSL.