... ...
Thursday, September 17, 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

Knicks Blame ‘Mistake’ for Sky-High High Ticket Prices

The team halted ticket sales and will issue partial refunds.
Brian Windhorst ESPN

Brian Windhorst Discusses Global Podcast Tour, LeBron’s Fanatics Deal

Windhorst also discussed the Clippers’ punishment and LeBron’s potential commute.
Exclusive

LeBron James Polymarket Deal Worth $15 Million a Year

James is not an investor in Polymarket, just an endorser.
Jun 24, 2024; Eugene, OR, USA; NBC Sports broadcaster Mike Tirico during the US Olympic Team Trials at Hayward Field. Mandatory Credit: Kirby Lee-USA TODAY Sports

Tirico Addresses Michael Jordan’s NBC Exit, Hopeful He’ll Return

Jordan served as a “special contributor” for NBC last season.
podcast thumbnail mobile
Front Office Sports Today

9/17/26 – CFB Ratings Surge, Joe Buck’s $108M Deal, Knicks Ticket Shock

0:00

Featured Today

Fantasy Football Drafts Are Turning Into Full-Blown Vacations

Leagues are foregoing solo drafts and replacing them with in-person getaways.
Oct 4, 2025; Tempe, AZ, USA; General action during the first period of the game between the Arizona State Sun Devils and the Penn State Nittany Lions at Mullett Arena
September 10, 2026

How Military-Style Workouts in College Sports Get Dangerous

For elite athletes, high-intensity training can be “very appealing.”
September 6, 2026

Is Carolyn Tisch Blodgett the Future Face of Giants Ownership?

Amid changes at top of Giants ownership, eyes are on Tisch Blodgett.
September 4, 2026

Wild Transfer Window Shows How Premier League Towers Over Soccer

Spending in England vastly outstripped the rest of Europe.
September 3, 2026

Teams Are Spending Millions to Build Luxury Locker Rooms

It’s a recruiting pitch, a retention tool, and a seven-figure line item.
Bhathals

Fire, Thorns Owners All In on Portland Despite Missing Out on Blazers

The sibling owners say Portland is a “mid-market unicorn.”
Exclusive
September 15, 2026

Carolyn Tisch Blodgett Says Giants Ownership Transfer Is Complete

The Tisch shares have been passed down.
September 15, 2026

Ndamukong Suh Blasts Rams’ ‘Asinine’ Australia Travel Plan

The Rams traveled to a game in Melbourne just a day before kickoff.
Sponsored

Drew Weatherford’s Bet on the Youth Sports Economy

Drew Weatherford discusses investing across the youth, college and professional levels.
September 14, 2026

Clippers Reverse Course and Accept NBA Punishment

Steve Ballmer said he has “sincere regrets.”
September 11, 2026

49ers Win Battle of Australia Travel Plans

The Niners blew out the Rams on Thursday.
Sep 9, 2026; Los Angeles, California, USA; Los Angeles Dodgers two-way player Shohei Ohtani (17) looks on during the first inning against the Cincinnati Reds at Dodger Stadium.
September 10, 2026

Ohtani Heads to Injured List as Dodgers Aim for Third Title

The two-way phenom is making a rare trip to the injured list.
September 8, 2026

Mayfield, Bucs Break Impasse With Three-Year Extension

The deal runs through the 2029 season.