Wednesday, October 21, 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

Want more from Front Office Sports
in your search results?

Add Front Office Sports on Google

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.

Download the FOS App

The business of sports, in your pocket.

QR code to download the app

Scan the QR code to get the app now.

Linkedin
Whatsapp
Copy Link
Link Copied
Link Copied

What to Read

LSU Won’t Roster Ex-NBA Player As SEC Legal Battle Continues

Louisiana AG Liz Murrill called again for the SEC’s lawsuit to be dismissed.

Adam Silver on LeBron Helicopter: ‘Perfectly Appropriate’

A source tells FOS the league is not investigating the matter.
Blake Griffin Front Office Sports

Blake Griffin: Clippers Haven’t Honored ‘Lob City’ Team

Griffin said the Clippers releasing Chris Paul was “disappointing.”
Aug 20, 2026; Dallas, Texas, USA; Basketball Hall of Famer Tracy McGrady looks on during the first half between the Dallas Wings and Indiana Fever at American Airlines Center.

Tracy McGrady Backs NBA’s Clippers Punishment: ‘Bad Business’

“Trying to circumvent the salary cap is just a no-no.”
podcast thumbnail mobile
Front Office Sports Today

10/21/26 – T-Mac Backs Clippers Penalty, 80-to-1 Rays Haunt Sportsbooks, Jay-Z Picks Jay-Z

0:00

Featured Today

Football - NFL - Houston Texans v Jacksonville Jaguars - Wembley Stadium, London, Britain - October 18, 2026 The necklace of a Jacksonville Jaguars fan outside the stadium before the match

Die-Hard Sports Fandom Has Reached the Afterlife

Will fans pay $6,000 to memorialize their team loyalty?
October 20, 2026

Why Europe Is Pumping Out NBA Superstars

The NBA and NCAA have an increasingly European flavor.
October 15, 2026

College Flag Football Is Outgrowing Its DIY Era

Women have been building the college game themselves at the club level.
Oct 5, 2026; Pittsburgh, Pennsylvania, USA; Pittsburgh Penguins general manager Kyle Dubas arrives at the arena before the Penguins host the Winnipeg Jets at PPG Paints Arena
October 12, 2026

NHL’s New Wave of GMs Is Built Different

“I am in the prediction business,” Devils GM Sunny Mehta tells FOS.
Action Images/Peter Cziborra
October 9, 2026

Is Leicester City’s $264 Million Price Tag Too Rich for Hungry Investors?

After falling from grace, how much is a former top club worth?
Oct 7, 2026; Bronx, New York, USA; New York Yankees right fielder Aaron Judge (99) against the Tampa Bay Rays in game three of the ALDS for the 2026 MLB Playoffs at Yankee Stadium.

Steinbrenner Lays Blame for Yankees Playoff Loss With Players

The club’s managing general partners made several pointed remarks.
Oct 19, 2026; St. Petersburg, Florida, USA; Tampa Bay Rays designated hitter Yandy Diaz (2) celebrates with teammates after hitting a two run home run against the Cleveland Guardians during the eighth inning in game six of the ALCS for the 2026 MLB Playoffs at Tropicana Field.
October 20, 2026

World Series Matchup Highlights Financial Savvy of Brewers, Rays

The two league champions used several shrewd moves to fuel their rise.
October 20, 2026

Jed York, Steve Tisch at NFL Owners Meeting After Scandals

York’s suspension is done.
Sponsored

Blake Griffin’s Plan for Media Domination

The former NBA star is building a second act across media & entertainment.
Jun 10, 2026; New York, New York, USA; New York Knicks guard Jalen Brunson (11) drives to the basket against San Antonio Spurs guard Stephon Castle (5) and forward Victor Wembanyama (1) during the first quarter of game four of the 2026 NBA Finals at Madison Square Garden.
October 20, 2026

Cheapest Ticket to Knicks Opener Climbs Above $2,000

New York begins its championship defense Tuesday night.
Oct 15, 2026; Los Angeles, California, USA; Milwaukee Brewers players celebrate after winning the NLCS for the 2026 MLB Playoffs against the Los Angeles Dodgers at Uniqlo Field at Dodger Stadium.
October 19, 2026

World Series Game 1 Tickets Reach Super Bowl Level Prices

Get-in pricing for Friday’s Game 1 is nearing $3,000 per ticket.
October 18, 2026

Ballhalla Lays Out the Blueprint For the WNBA

Golden State has sold out every home game this year.
October 18, 2026

Another Eagles Reset? Losing Streak, Hurts’s Contract Loom Large

The Eagles’ struggles could prompt another organizational overhaul.