Kawhi Leonard Became the Measure, Drake’s Diss Reminds Everyone What DeRozan Couldn’t Deliver

Drake has turned up the heat again in his ongoing tension with DeMar DeRozan, further intensifying their feud with a new leaked snippet where he appears to question DeRozan’s ability to bring a championship to Toronto. In that same track, Drake also references Kawhi Leonard, deepening the rivalry while reminding fans of what changed after the blockbuster trade in 2018.

The History: DeRozan in Toronto Before the Trade

From 2009 through 2018, DeMar DeRozan was a central figure for the Toronto Raptors. He showcased exceptional scoring, loyalty, and connection with fans, but despite many strong seasons and playoff appearances, the championship remained out of reach.

In 2018, Toronto made a controversial trade sending DeMar DeRozan to the San Antonio Spurs in exchange for Kawhi Leonard. Under Kawhi’s leadership, Toronto won its first NBA Championship in 2019, defeating the Golden State Warriors 4‑2 in the Finals. That trade became a turning point in Raptors’ history and forever altered the comparison between DeRozan and Leonard.

How the Rivalry With Drake Started

Drake’s beef with DeMar DeRozan is rooted in multiple events. One early spark was DeRozan appearing in Kendrick Lamar’s “Not Like Us” music video, a track widely interpreted to include bars toward Drake. DeRozan also performed at the “Pop Out: Ken & Friends” concert in Inglewood, California, during Lamar’s set. That show took place on Juneteenth, and many view DeRozan’s participation as symbolic.

In November 2024, during a Raptors vs. Kings game held in Toronto, Drake was seen courtside and made sharp comments about DeRozan. He said that if the Raptors ever retired DeRozan’s jersey banner, he would personally remove it. He also called DeRozan a “goof” live during the broadcast. That moment was widely viewed as bringing the feud into the open. The Sacramento Kings, DeRozan’s current team, responded by supporting him publicly, including via social media. The Kings posted footage of the jersey one fan threw on stage when Drake spiked it, captioned with love for DeMar DeRozan — “the 916 loves Deebo.” That incident occurred in Sydney, Australia, during a Drake concert in February 2025, and went viral.

The Leaked Track Snippet: Lyrics That Stab

A new snippet from Drake’s upcoming album Iceman has added yet another layer to this feud. In that leaked verse, Drake raps:

“When you was part of the team we used to be planning our Mexico trips in the spring, we must’ve been dealing in the spur of the moment ‘cause why (Kawhi) did we think you could get us a ring?”

These lines challenge DeMar DeRozan directly—suggesting that during his time with Toronto, fans or insiders believed he could deliver a title, but that expectation may have been misplaced. By mentioning Kawhi Leonard, Drake is drawing comparison: after the trade, Kawhi did deliver. This is not just shade—it’s a reminder of what happened after DeRozan was traded away.

Kawhi Leonard’s Shadow in the Narrative

Kawhi Leonard becomes a central figure in Drake’s jab. His arrival in Toronto post‑trade and the subsequent 2019 championship are now used as benchmark moments. In discussions and lyrics, Kawhi is often held up as proof that what people believed DeRozan could not do, Kawhi did under intense pressure.

By invoking Kawhi in the new track, Drake reminds listeners of the results—something championship proof carries. It’s not merely about talent or loyalty; it’s about delivering when it matters most. This comparison has stung many Toronto fans because it frames success in very specific terms, pushing DeRozan’s legacy into a test of output versus potential.

DeRozan’s Responses and Where He Stands Now

DeMar DeRozan has in public speeches and interviews addressed the tension with maturity. He often refers to being loyal, to his time with Toronto, and to what he meant to the city. He acknowledges that the trade was painful for many fans but remains proud of what he built.

Since joining the Sacramento Kings, DeRozan has taken on a different role—less often the primary star, more often leader, veteran, scorer and guide. His adaptability becomes a testament to his enduring value, even in the presence of criticism from public figures and rivals.

He has spoken about how loyalty, consistency, and character also matter, not just championships. For many fans, he remains beloved because of what he represented in Toronto, even if championship hardware came later with someone else.

Public Reaction, Social Media, and Fan Sentiment

When the leaked snippet appeared, social media exploded.

Some fans believe Drake has a valid point: if expectations were set during DeRozan’s tenure, the failure to reach the Finals or win the title becomes part of what people remember most.

Others argue that it is unfair to judge DeMar DeRozan only in terms of championship wins. They point out the many variables in basketball: roster construction, coaching, match‑ups, injuries, and luck. For many, DeRozan’s legacy includes his scoring, his commitment to Toronto, his community presence, and how he responded under pressure in Sacramento.

The Sacramento Kings fan base and observers have come to see DeRozan’s current performance as an opportunity to redefine his legacy beyond what happened in Toronto. Wins, leadership moments, and resilience are now under the microscope.

Role of Teams, Time, and Places That Mattered

Toronto Raptors (2009‑2018) is seen as the era where expectations were high for DeMar DeRozan, but results lagged.

San Antonio Spurs, as the team that got DeRozan in the trade in exchange for Kawhi Leonard, play an important role in this story. That trade happened in the summer of 2018. 2019 Finals became the measuring stick.

Sacramento Kings, his current team, show how DeRozan has remained relevant and respected, even as the narrative around him shifts.

Concerts and places matter too: the “Pop Out: Ken & Friends” concert at Kia Forum in Inglewood, California, in June 2024. The show where DeRozan joined, and where the audience responded. The Australia concert in February 2025 where Drake spiked the Toronto Raptors jersey live on stage.

Implications For DeRozan’s Legacy and Identity

Legacies in the NBA are often judged by championships. For DeMar DeRozan, this feud makes that fact more visible. The comparison with Kawhi Leonard is not just about teams, but about whether a player can seize a moment, deliver ultimate success, and thus change how history sees them.

For Toronto, many fans feel that DeRozan deserves more acknowledgment for what he brought—leadership, consistency, heart—even if a ring didn’t arrive until after he was traded.

For DeRozan in Sacramento, it’s a chance to build a fresh chapter. The expectation is that he continues to lead, to win meaningful games, to push the team deeper. His performance in the upcoming season matters not just for playoffs, but for the narrative around what defines greatness.

How Drake’s Role Plays Into Hip Hop and Sports Culture

This beef reflects the increasing overlap between hip hop and NBA culture. Drake, as a rapper and a Toronto native, holds significant influence. His statements, lyrics, and public behavior affect how fans perceive players. When he references trades, rings, and loyalty, these are not just entertainment—they shape narratives, fan memory, and also player reputation.

The fact that the track blaming DeRozan for not delivering a ring comes in an album titled Iceman adds style and drama. It’s part of the ritual of beef in rap: songs, leaks, references, concerts. Each moment adds weight.

What to Watch in the Coming Season

Will DeMar DeRozan respond in music, in public interviews, or through performance? Will Drake release the track officially, and will it be more direct? How will Toronto Raptors fans react during banner discussions? Will there be any revocation or acknowledgment?

In Sacramento, the pressure is on DeRozan to lead, to perform in front of fans who may or may not feel sympathy. Key games against Toronto, public appearances, clutch moments will be especially scrutinized.

And for Drake, how this beef affects his image can ripple—fans love rivalry, but they also respect authenticity. If the diss is seen as disrespectful, or unfair, there’s backlash potential. If it’s viewed as valid critique, many will praise the sharp lyrics and honesty.

Conclusion: More Than Just Beef

This isn’t simply about dissing someone in a song. Drake Escalates DeMar DeRozan Beef With Brutal Diss While Showing Love To Kawhi Leonard In Latest Track encapsulates something deeper: how legacy, loyalty, performance and public perception intertwine in both basketball and music.

DeMar DeRozan remains a cherished figure, not just because of scoring or plays, but because of what he represented in Toronto. The comparison with Kawhi Leonard after the trade is a dramatic narrative arc. Drake, by bringing up those memories, is reminding fans what changed—and challenging what fans expect.

In the end, it’s a story about expectations versus outcome, about what gets remembered, and about how one moment, one trade, one championship can shift the meaning of everything that came before. As the next season unfolds, DeRozan’s actions — on court and off — and how he resists or responds to this narrative will be among the most interesting storylines in both sports and culture.