Two years from winning their first NBA championship, the Raptors missed the playoffs for the first time since 2013.
While it is easy to label this season a disappointment, it is important to point out the circumstances that Toronto faced this season. COVID-19 restrictions left the Raptors without a home and forced them to play in Tampa, Florida for the entire season.
After climbing to .500 in late February, Toronto endured a COVID-19 outbreak that sidelined most of their coaching staff and key players, including Fred VanVleet, Pascal Siakam and OG Anunoby.
Toronto would go on to lose thirteen of its next fourteen games.
Despite a likely appearance in the lottery, there is still a foundation in place led by VanVleet, Siakam, Anunoby and Gary Trent Jr.
Toronto also moved up in the draft lottery, now having the No. 4 pick.
The big question this offseason will center around free agent Kyle Lowry, Trent (who is a restricted free agent) and what the future holds for team president Masai Ujiri, who is in the last year of his contract.
The free agency of Kyle Lowry
The future of Lowry took a U-turn at the trade deadline when the Raptors elected not to move the franchise guard but instead hold on to him for the remainder of the season.
The decision was smart, because the Raptors front office is no longer pressed up against a 3 p.m. ET deadline to decide on Lowry's future. They now have the entire offseason to determine in which direction they want to go.
"Honestly, our team can go in many different directions," Raptors president Masai Ujiri said after the deadline in March. "I keep saying it. We are comfortable with whatever direction we go. Maybe we lost a chance here, but we also think we gained a chance in some other things going forward. This team, especially with what we've gone through this year, could pivot in many different directions. This is where we find ourselves now."
What direction Toronto chooses, will dictate how they add to the roster in free agency.
Letting Lowry walk
Lowry became more expandable the night of the lottery when Toronto jumped from 8th to 4th. The top-5 slot now has the Raptors staring at guards Jalen Suggs, Jalen Green or possibly a big in Evan Mobley.
In the scenario that Lowry does not return or a sign-and-trade does not materialize, Toronto would be looking at $15 million in cap space this offseason, accounting for the 10 players under contract (including the Raptors' first-round pick) and the $4.7 million hold of restricted free agent Gary Trent Jr. Veterans Rodney Hood and Aron Baynes would be waived to create room.
Toronto's cap space could increase to $18 million if DeAndre Bembry, Paul Watson, Yuta Watanabe and Freddie Gillespie are waived.
The Raptors could also gain an additional $2.6 million in room if they pull the qualifying offer from Trent but have an understanding the guard would not entertain offers from another team. That would reduce Trent's cap hold from $4.7 million to $2.1 million. Toronto could then use its cap space before circling back to re-sign Trent.
This could be the last time for the foreseeable future that Toronto has cap space to sign an outside free agent. Trent's eventual new deal will take up a chunk of Toronto's future space, and Chris Boucher is likely in line for a new pact in 2022.
However, the Ujiri hasn't needed cap space in the past, choosing to build Toronto's roster with shrewd trades (Kawhi Leonard and Trent), identifying undrafted players (VanVleet and Boucher) and drafting players outside of the lottery (Anunoby and Siakam).
The last time the Raptors used room was in 2015 when they signed DeMarre Carroll to a four-year $58 million contract. Two years later, Carroll was sent to Brooklyn in a salary dump that cost the Raptors a first and second-round pick.
If the Raptors do go the cap space route, expect them to build out their bench with multiple players rather than trying to hit a home run with one player in the $20 million range.
Bringing Lowry back
In an ideal world, Lowry would finish his career in a Raptor uniform.
"I think we all know the respect and the sentiment about Kyle and this ball club, and what he's done not only for the city, the team, the country, the league," Ujiri said.
Just look at what Lowry has accomplished since he was traded to Toronto from Houston on July 12, 2011: seven consecutive playoff appearances, six All-Star games, All-NBA in 2016 and most importantly leading the Raptors to their first NBA championship in 2019.
He also ranks second in franchise history in games and minutes played.
Despite all the accolades and nostalgia, the reality is that the Raptors and Lowry have to put those sentiments aside to reach a compromise on what a new contract would look like.
Lowry turned 35 years old in March. Although he will finish this season with the second-fewest games played in his career (he played only 10 his rookie season with Memphis), he still ranked eighth among point guards in real plus-minus.
According to ProFitX, Lowry's salary projection is a contract that starts at $27.1 million, $3 million less than his salary for the current season. The projected salary would rank 14th among point guards.
The sticking point to a new contract will not come down to dollars but years.
Since 1999, there have been only two players 35 years or older who signed a multiyear contract with a starting salary of more than $25 million: Dirk Nowitzki (two years, $50 million in 2016) and LeBron James (a two-year, $85.6 million extension earlier this season).
It is one thing to pay Lowry a $27 million contract for one season but another to commit a lucrative salary long-term when he will be 37 and 38 years old. Because of the Over 38 rule, the maximum years that Toronto can give on a new deal is three.
Note: ProFitX is a dynamic financial and performance index powered by Artificial Intelligence with front-office optics displaying 17 visual and time-series models for 480+ NBA Athletes. The Athledex models historical, dynamic & future performance data to monitor and project insights on contracts, performance, injuries, team fit, development, and potential.
Working a sign-and-trade
The past two free agent periods have proved that there are other resources to acquire high-level players outside of cap space.
In 2019, the Miami Heat had zero cap space but were able to acquire Jimmy Butler in a complex sign-and-trade with the Philadelphia 76ers. The same applied for the Houston Rockets this past November when they acquired free agent Christian Wood.
For Lowry, the sign-and-trade option comes into play if the pool of teams with cap space dry up or the Raptors elect to go in a different direction and not sign him. Although the sign-and-trade is an option, it requires cooperation from the Raptors.
Right now, only two playoff teams -- Miami and the New York Knicks -- both project to have room and need a point guard.
The Heat were a possible Lowry destination at the trade deadline and, despite having room to sign Lowry outright, Miami could end up as a sign-and-trade partner (which would allow the Heat to operate as an over-the-cap team and retain free agent Victor Oladipo, Trevor Ariza or exercise the team option of Andre Iguodala).
A package centering on Goran Dragic works, but that would see Toronto punting on free agency. Dragic has a $19.4 million contract (his team option would be exercised) which would eliminate what the Raptors have in cap space.
There is also the obstacle that Lowry would have to sign a three-year contract (only the first year needs to be guaranteed) and the receiving team would now be hard capped.
What is the cost of Gary Trent Jr.?
Acquiring Trent at the trade deadline bought the Raptors an insurance policy.
Unlike Norman Powell, who is set to become an unrestricted free agent this offseason if he opts out of the final year of his contract, Trent is a restricted free agent. The restricted tag allows Toronto the right to match on an offer sheet.
There are two schools of thought on how the Raptors approach a new contract with Trent.
The first is to let Trent set the market and shop for an offer sheet from a team that has room. The downside is Toronto could be waiting a long time since there are only five teams projected to have room: Charlotte, Miami, New York, San Antonio and possibly Oklahoma City. The last thing the Raptors want is for Trent to accept the $4.7 million qualifying offer, making him an unrestricted free agent in 2022.
The second option would be to take a proactive approach like Minnesota did with Malik Beasley, agreeing to a four-year $60 million contract on the first day of free agency.
The career paths of Beasley and Trent are comparable. Like Trent, Beasley was a reserve before he was traded to Minnesota, starting only 33 games in three and half years with the Denver Nuggets.
Trent started when CJ McCollum went down with an injury but primarily served as a sixth man in his two and half years with the Portland Trail Blazers. In the 23 starts in Portland, Trent averaged 18 points on 39.7% from three.
Since the trade to Toronto, he has averaged a career high in minutes (31.8) and points (16.6). His career high of 44 points (on 17-of-19 from the field) occurred in a Raptor uniform back in early April.
Trent was eligible for a four-year, $53 million extension with the Trail Blazers but elected to play out the season and become a restricted free agent.
The big question now will be if that was a mistake or will he earn more in free agency?
Offseason cap breakdown
Which direction the Raptors go in with Lowry will dictate if they are a team over the cap or have money to spend in free agency.
If Lowry returns on a $25 million contract, Toronto would likely have to waive Hood and Baynes to stay under the luxury tax. That takes into account signing Trent to a $13-14 million contract and using part of their $9.5 million midlevel exception on Khem Birch.
In the event that Lowry signs elsewhere, the Raptors could have up to $18 million in room but with only Siakam, VanVleet, Anunoby, Boucher, Malachi Flynn, their first-round pick and the restricted hold of Trent.
That would also leave them with the $4.9 million room midlevel exception, though they'd lose the larger midlevel exception by operating as an under-the-cap team.
Team needs
Kyle Lowry
Starting shooting guard
Depth at shooting guard and small forward
Stretch four
Resources to build the roster
Own free agents: Lowry and Trent
Projected cap space: $23M (if no Lowry)
The draft: first-rounder
Exceptions: $9.5M midlevel and $3.7M biannual or $4.9M room midlevel
$5.8M in cash to send or receive in a trade
Dates to watch
• By the first day of August, the Raptors will give Trent a one-year $4.7 million qualifying offer. The contract will put the restricted tag on the shooting guard, allowing the Raptors to match an offer sheet from an opposing team. The qualifying offer was originally $2.1 million but increased to $4.7 million when Trent Jr. started 36 games this season.
• Don't expect Boucher to hit the waiver wire in early August. After signing a two-year $13.5 million contract, Boucher has emerged into one of the great success stories this season. After suffering a torn ACL in his senior season at Oregon, leading him to go undrafted in 2017, Boucher has put together a career year with the Raptors. A candidate for Most Improved Player, the 28-year old averaged 13.6 points, 6.7 rebounds, shooting 52% from the field and 38.9% from three. His $7.0 million contract for 2021-22 becomes guaranteed at 5 p.m. ET on August 8.
• While Boucher will be on the roster past his guaranteed date, the same cannot be said for Baynes. Signed to a two-year $14.3 million contract in the offseason, Baynes struggled this season to find a role. After starting his first 24 games of the season, he has now come off the bench in 19 of his past 27 games (and hasn't played since April 10). His $7.35 million contract becomes guaranteed if he is not waived by 5 p.m. ET on August 5.
• Unlike the Boucher and Baynes decisions that will occur after free agency starts, the Raptors must decide on the $10.9 million contract of Hood by July 27. Acquired from the Trail Blazers in the same deal that landed Trent, Hood appeared in 17 games for Toronto. Before suffering a torn left Achilles on Dec. 4, 2019, Hood had started 21 games with Portland, shooting a career high 49.3% from three and averaging 11 points.
• The Raptors did a smart thing staggering the guaranteed dates for DeAndre' Bembry ($1.97 million) and Watson ($1.7 million). Although each has a small cap impact that would not tilt the scale when it comes to cap flexibility, guaranteeing each contract contract counts toward the 15-man roster. In 36 games coming off the bench (he also started 11), Bembry averaged 15.0 minutes and 4.2 points. The Raptors have until August 7 to guarantee his contract. Watson went from averaging 4.6 minutes before the All-Star break to 20.2 in 11 games. He had a career high 30 points in a win against Orlando. The guaranteed date for the undrafted 26 year old is August 6.
• The contract for Watanabe will increase from $0 salary protection to $375K if the forward is not waived by August 9. The remaining $1.4 million in salary becomes guaranteed if Toronto has not requested waivers by the first game of the regular season.
• Like Watanabe, Gillespie was signed to a two-year contract at the end of the regular season. His $1.5 million contract is non-guaranteed and has $50K in protection if he is on the roster past August 20. It becomes full if he is not waived by the first game of the regular season.
Restrictions
• The poison pill restriction for Anunoby gets lifted on August 3.
• The non-guaranteed contracts of Boucher, Hood, Baynes, Bembry, Watanabe, Watson and Gillespie have no trade value until their contracts are guaranteed.
Extension candidates
• There are no players on the roster who are eligible for a contract extension.
The draft
Since Masai Ujiri took over in 2013, the Raptors have had their own first-round pick in every draft except for 2018 (sent to Brooklyn in the salary cap dump of DeMarre Carroll) and 2019 (sent to San Antonio as part of the Kawhi Leonard trade).
This July, the Raptors have three selections: their own first and two seconds (from Golden St. and Memphis). They also have their own first in all future years.
Here's how ESPN's Jonathan Givony and Mike Schmitz have Toronto selecting in July:
No. 4 (own): Jalen Suggs, PG/SG, Gonzaga
No. 44 (via GSW): Ariel Hukporti, C, Germany
No. 47 (via MEM): Matthew Hunt, PF, Duke
In his tenure with the Raptors, Ujiri has made two trades during the draft. The most notable came in 2015, when Toronto sent Greivis Vasquez to Milwaukee for the rights to Norman Powell (No. 46 pick) and a 2017 first from the LA Clippers.