By Pete Baxter
Kyle Lowry and DeMar DeRozan are two legends of Toronto Raptors basketball. They are undoubtedly two of the top five players in that franchise’s history. During their six seasons together in Canada, they were both four-time All Stars and helped build the Raptors into perennial contenders in the Eastern Conference. They hit their peak coming just two wins away from the NBA finals in a 4-2 series loss to Lebron James’ Cavaliers in the 2015/16 Eastern Conference Finals.
Ultimately, DeMar DeRozan was traded in a blockbuster deal to the San Antonio Spurs for disgruntled, oft-injured superstar Kawhi Leonard prior to the 2018/19 season. Kawhi turned his one-year stay in Toronto into the franchise’s first NBA title, while DeMar DeRozan has kept the Spurs in the middle of the pack in the Western Conference.
Lowry and DeRozan had made no secret that were best friends on and off the court. Thus, it was no surprise that both stars were shocked and disappointed after learning that DeRozan had been dealt. Lowry famously did not speak to Raptor’s leadership for weeks following the deal. DeRozan was vocal about feeling betrayed by Masai Ujiri and company, who earlier in the offseason had assured him he would not be dealt.
Fast forward to 2021. Both players find themselves entering unrestricted free agency in the offseason.
It would be one of the great fairytale storylines in NBA history if these two All-Star best friends were able to reunite and chase championship success together again late in their careers. Kyle Lowry is the elder of the two at 35 years old, while DeRozan is 31. Both are still playing at borderline All-Star levels and could certainly contribute to a championship contender.
It seems safe to say the two players have discussed this possibility together, but are there any teams who would have the financial flexibility and the interest in bringing in these two Raptors legends?
A Reunion in Toronto is Unlikely
Raptors fans and pundits around the internet have thrown out the idea of a Lowry/DeRozan reunion in Toronto next season. This is most likely just fodder for discussion forums, however. It seems like a highly unlikely scenario.
For starters, the Raptors finally seem poised to move on from the Kyle Lowry era. Fred VanVleet is the point guard of the future in Toronto, and Malachi Flynn seems ready to be the primary backup. Therefore, it would make little sense for the Raptors to invest the $25 million+ annually it would take to keep a 35-year-old point guard in house.
As noted, DeMar DeRozan was furious with Raptors’ brass after being dealt to San Antonio. It would be hard to imagine he would consider a return to the franchise that betrayed him.
It would make even less sense for the Raptors to invest an additional $25 million+ to bring back a star they had clearly moved on from three years back. At that time, Masai Ujiri and Bobby Webster determined they had seen the ceiling of the Lowry/DeRozan pairing, and it was less than a championship. It would be difficult to see a reverse in that philosophy.
Additionally, to take on this pair of stars, the Raptors would have to part with several of their key young assets to make the money work. So most likely this would be a no-go.
With the Raptors crossed off of the list, let’s take a look at three teams that could actually consider bringing the Lowry/DeRozan duo to town:
The Dallas Mavericks
By the end of their run in Toronto, it was clear that Kyle Lowry and DeMar DeRozan were not a dominant enough duo to be the top two options on a championship squad. However, as second and third options, it could be a different story.
Enter the Dallas Mavericks. Luka Doncic was a one-man army for the Mavericks this season. He put up superhuman numbers in single-handedly taking the Clippers to seven games in this year’s playoffs. He averaged 35.7 points, 7.9 rebounds and 10.3 assists during the series. However, the Mavericks ultimately lost because he received little help from the rest of his squad.
His supposed number two option, Kristaps Porzingis, was essentially a no-show in the series. Porzingis averaged just 13.1 points, 5.4 rebounds and 1.3 assists through seven games. He also expressed frustration in his role playing alongside Doncic, saying he felt like an “afterthought.” Signs seem to be pointing to a breakup in the relationship between Porzingis and the Mavericks in the offseason.
The Mavericks could potentially strengthen the supporting cast around Doncic by bringing in Kyle Lowry and DeMar DeRozan. Financially, this could be achieved by arranging a sign-and-trade deal centered around Porzingis and one of the former Raptors.
For example, if the San Antonio Spurs signed DeRozan to a three-year deal worth $23 million per year, they could swap DeRozan for Porzingis straight up. With the money they would save between the difference of DeRozan’s deal and Porzingis’ $31.6 million salary next year, along with their existing cap space, the Mavericks could then sign Kyle Lowry as a free agent for a similar deal to DeRozan in the $20 to $25 million annual salary range.
Where would this leave the theoretical Mavericks line up next season? Let’s take a look:
PG: Luka Doncic
SG: Kyle Lowry
SF: DeMar DeRozan
PF: Dorian Finney-Smith
C: Maxi Kleber
Kyle Lowry would bring the championship pedigree and toughness that this team was lacking last season. While a natural point guard himself, he has played productively in dual point guard lineups with Fred VanVleet for the past two seasons and could be an intriguing backcourt match with Doncic. DeMar DeRozan would replace Porzingis as the second offensive option on this squad as a consistent 20+ point per game scorer. If the Mavericks were also able to retain Tim Hardaway Jr., he could be one of the top sixth men in the league or join this lineup for a deadly small ball approach.
With the additional support of the Lowry/DeRozan duo, Luka could easily breakthrough next season and lead the Mavericks on a deep playoff run.
The New York Knicks
The Knicks, under head coach Tom Thibodeau, shocked the NBA world by returning to the playoffs for the first time in nearly a decade. They did it with only one All-Star in power forward Julius Randle, and without a true starting-caliber point guard. While Derrick Rose was dynamic off the bench, neither Elfrid Payton nor rookie Immanuel Quickley were ready for playoff basketball.
The Knicks have the most cap space of any team this offseason and could conceivably sign two stars to near-max deals. By targeting DeMar DeRozan and Kyle Lowry, they would bring in two All-Star level talents that would fit perfectly into their existing scheme. This would still leave cap room open to potentially re-sign key role players like Nerlens Noel and Derrick Rose.
Kyle Lowry would finally solve the point guard problem that has plagued the Knicks seemingly throughout their history. DeRozan would be an outstanding number two scoring option next to Julius Randle. The added firepower of this duo would free up R.J. Barrett for more looks and help with his own continued development. Not unlike Fred VanVleet in Toronto, Immanuel Quickley would be tutored under one of the top point guards and best leaders in the league in Kyle Lowry.
Where would the addition of Lowry and DeRozan leave the Knicks potential lineup next year? Let’s take a look:
PG: Kyle Lowry
SG: R.J. Barrett
SF: DeMar DeRozan
PF: Julius Randle
C: Nerlens Noel
This could usher in a new golden age of basketball at Madison Square Garden. Suddenly the Knicks would have three All-Star level talents in Randle, DeRozan and Lowry along with a potential future superstar in Barrett.
This Knicks squad without these two stars already finished fourth in the Eastern Conference this past season. The addition of Lowry and DeRozan could easily turn them into contenders.
Los Angeles Lakers
Lastly, we have the LA Lakers. We know Lebron James is one of the top recruiters in the NBA, and after a disappointing and unprecedented first-round playoff exit, there is no question he is on the look out for more star power to join himself and Anthony Davis at Staples Center.
The Lakers’ back court this past season was a point of weakness. Dennis Schroder was an absolute disaster in the playoffs, including a zero-point, one assist performance against Phoenix. It seems safe to say that his days as the starting point guard in LA are numbered, as he enters free agency himself.
Shooting guard Kentavious Caldwell-Pope is a solid role player and good two-way player, but he is likely not the wing weapon the Lakers need next to Lebron James to truly contend moving forward.
Should the Lakers target Lowry and DeRozan this offseason, they could significantly upgrade both backcourt positions. Lowry, an NBA champion known for his toughness, would be a significant upgrade over Schroder, particularly in the playoffs. DeRozan, who has proven himself capable of leading a team to the playoffs as number one option in both Toronto and San Antonio, would be an outstanding third or fourth offensive option in LA.
To achieve these moves financially, the Lakers would likely need to work at least one sign-and-trade deal to create the necessary cap space. Should the Raptors sign Kyle Lowry to a two-year deal worth $25 million per season, the Lakers could send Kyle Kuzma, Kentavious Caldwell-Pope and a first-round pick to Toronto to acquire Lowry.
By letting free agents Schroder and Montrezl Harrell walk (Harrell is expected to decline his player option), they would have the cap space to then sign DeMar DeRozan as a free agent.
Where would this leave the Lakers’ lineup next season? Let’s take a look:
PG: Kyle Lowry
SG: DeMar DeRozan
SF: Lebron James
PF: Anthony Davis
C: Marc Gasol (if Andre Drummond is not re-signed)
Suddenly the Lakers have at least four All-Star caliber players in their starting line-up and four NBA champions (if Gasol enters the season as starting Center).
Not unlike this past season, the success of the Lakers will depend largely on the health of James and Anthony Davis. However, with Lowry and DeRozan in-house, there is suddenly a tandem of stars with six years of chemistry and playoff success together to carry the load should Davis or James miss time.
The Lakers would likely enter 2021/22 as favorites for the chip.
Also, it must be noted that uniting Lowry and DeRozan with Lebron James, who almost single-handedly kept the Raptors from making it out of the Eastern Conference for the better part of a decade, would be an amazing piece of NBA lore.
While it may be a longshot, there is no question that the interest is there for best friends Kyle Lowry and DeMar DeRozan to play together again. Both are in their thirties and would no doubt love the opportunity to chase a ring together again.