Tuesday, May 26, 2026

Raptors’ Win-Now Rebuild?

  • Rather than reach for another “superstar,” Masai Ujiri has continued to entrust Pascal Siakam and stick with Fred VanVleet.
  • In Feb. 2021, VanVleet became the highest-paid undrafted free agent in league history.
Benny Sieu-USA TODAY Sports/Design: John Regula

The Raptors played the entire 2020-21 season in Tampa Bay, lost six-time All-Star Kyle Lowry last offseason, and are currently playing with no fans due to Ontario’s COVID policy.

In 2018, Toronto had traded franchise face DeMar DeRozan for Kawhi Leonard, who delivered a title — but immediately left for L.A., signaling what many thought would be a long-term rebuild.

Yet, on a three-game win streak following Tuesday’s win over the Heat, Toronto is the East’s 8-seed. Credit is due to president Masai Ujiri.

  • Rather than reach for another “superstar,” Ujiri has continued to entrust Pascal Siakam (21 PPG) and stick with Fred VanVleet (21.5 PPG), who in Feb. 2021 became the highest-paid undrafted free agent in league history (four years, $85M).
  • They traded Norman Powell for Gary Trent Jr. last season. On Tuesday, Trent Jr. became the fourth player ever to record 30+ points and 5+ threes in five straight games.
  • They signed fourth-overall pick Scottie Barnes for four years, $33 million. He has the third-best odds to win Rookie of the Year (+550*).

Plus, Goran Dragic’s $19.4 million deal expires after this season, which will give the Raptors roughly $18 million in cap space

It’s no surprise that Ujiri is the mastermind behind it all. The one-time Executive of the Year is paid an AAV of $15 million — more than nine players on the team’s payroll.

Even if they don’t make a deep playoff run, the organization has managed to balance continued success and roster regeneration.

This field is for validation purposes and should be left unchanged.

Sign up for
The Memo Newsletter

Get the biggest stories and best analysis on the business of sports delivered to your inbox twice every weekday and twice on weekends.

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.
Linkedin
Whatsapp
Copy Link
Link Copied
Link Copied

What to Read

May 25, 2026; Cleveland, Ohio, USA; New York Knicks lift the 2026 Eastern Conference trophy after defeating the Cleveland Cavaliers in game four of the eastern conference finals for the 2026 NBA playoffs at Rocket Arena.

Title-Starved Knicks Fans Push Finals Tickets to $3,700

Demand for games at Madison Square Garden reaches Super Bowl-like levels.

James Dolan’s Controversial $30M Thibodeau Firing Has Paid Off

Mike Brown has the Knicks in their first Finals since 1999.
May 25, 2026; Cleveland, Ohio, USA; New York Knicks forward OG Anunoby (8) high fives New York Knicks center Karl-Anthony Towns (32) in the fourth quarter against the Cleveland Cavaliers during game four of the eastern conference finals for the 2026 NBA playoffs at Rocket Arena.

Knicks Reach First NBA Finals Since 1999

The Knicks are looking for the franchise’s first NBA title since 1973.

Featured Today

May 24, 2026; Evanston, IL, USA; Northwestern Wildcats attack Kathryn Ratanaproeksa (13) shoots against the North Carolina Tar Heels during the first half at Martin Stadium

Can Women’s Lacrosse Buck the Trend in College Sports?

The sport is fighting to prove its worth in the revenue-sharing era.
May 22, 2026

Big Money on the Line on Premier League’s Final Day

Arsenal has won the title, but millions are still at stake.
Texas State mascot
May 22, 2026

Mascot-Reveal Videos Are the Newest College Sports Tradition

Student mascot unmasking videos are going mega-viral.
Charlie Pliner and Nikolas Rohrmann
May 22, 2026

How 2 Brown Undergrads Became Sports Dealmakers

An experimental project turned into a permanent course and business deal network.

Pochettino Defends How He Delivered World Cup Roster News

Pochettino said calling players who got cut would’ve been “bullshit.”
Nov 20, 2025; Salt Lake City, Utah, USA; Vegas Golden Knights head coach Bruce Cassidy watches play against the Utah Mammoth during the third period at Delta Center
May 20, 2026

NHL Coaches’ Association Pushes Back on Vegas Cassidy Restrictions

Vegas is within bounds, but the move is unusual and controversial.
May 22, 2026

Man City’s Pep Guardiola Is Leaving: ‘Don’t Ask Me the Reasons’

The six-time Premier League winner ends his epic run one year early.
Sponsored

The Hidden Economy of Race Weekend

Learn more about the Vintage Flying Museum and how Spectrum Business is helping them achieve their business goals while fueling their dreams.
May 19, 2026

Trail Blazers Lay Off Dozens As Tom Dundon’s Cuts Continue

The team confirmed the departures in a statement Tuesday.
May 19, 2026

Arsenal Wins First Premier League Title Under American Owners

The Gunners hadn’t won England’s top league since 2004.
May 4, 2026; New York, New York, USA; New York Knicks guard Josh Hart (3) controls the ball against Philadelphia 76ers forward/guard Kelly Oubre Jr. (9) during the first quarter of game one of the eastern conference semifinal round of the 2026 NBA Playoffs at Madison Square Garden.
May 18, 2026

Knicks Ticket Demand Sees MSG Get-In Prices Soar

Resale ticket prices for any potential Finals games at MSG begin at about $2,500.
May 13, 2006; Washington, D.C, USA; FILE PHOTO; Houston Comets at Washington Mystics -- Houston forward Sheryl Swoopes brings the ball up court.
May 14, 2026

Houston WNBA Team Expects to Keep Comets Name

The Connecticut Sun will move to Houston in 2027.