3 Raptors Trades Turned Pascal Siakam into Kawhi Leonard

Every move a front office makes in the NBA leads to the next, and that couldn't be more true for the Toronto Raptors.

In their three decades of history, everything has led to the 2026-27 season, which will see the return of franchise legend Kawhi Leonard, who was dealt to the Raptors once again after being their blockbuster trade target eight years ago with the San Antonio Spurs.

The journey that has him coming back to Toronto is definitely one for the books.

2019: Kawhi Leonard Leaves for Clippers

Kawhi Leonard walks towards the team bench during a timeout against the Sacramento Kings. | USA TODAY Sports

After winning the championship with the Raptors in 2019, Leonard opted for free agency, which gave him a chance to pick his team for the first time in his career. Leonard wanted to play close to home in Southern California, so he signed with the Los Angeles Clippers just weeks after winning his second championship.

The Raptors knew this was a possibility upon making that trade in 2018, but they rolled the dice anyway. It paid off, but they ultimately paid the price of losing him for nothing in free agency.

2020: Pascal Siakam Becomes an All-Star

Pascal Siakam participates in the skills challenge during NBA All Star Saturday Night. | USA TODAY Sports

The Raptors were forced to pivot after losing Leonard, but they looked within to find his replacement. Enter Pascal Siakam, a 2016 first-round pick who didn't become a full-time starter until the 2018-19 campaign. He became the league's Most Improved Player of the Year and took on more responsibility during the 2019-20 campaign. For the first time in his career, he averaged more than 20 points per game and was an All-Star for the first time.

The Raptors had a higher winning percentage the year after they won a championship than they did the year prior, largely due to Siakam's ascent. The Raptors built around Siakam, but they were unable to achieve the same levels of success that Leonard did.

2021: Raptors Take Scottie Barnes

Scottie Barnes (Florida State) poses with NBA commissioner Adam Silver after being selected as the number four overall pick. | USA TODAY Sports

Two years after the Raptors won a championship, they became a lottery team. They were unable to maintain that roster, but Siakam was the primary piece that stayed intact. It ultimately led to the team getting the No. 4 overall pick in the 2021 NBA Draft, where they took Florida State forward Scottie Barnes.

2024: Pascal Siakam Traded to Pacers

The Raptors attempted to build their roster around Barnes and Siakam. While they became a playoff team in 2022, they were unable to keep that going in 2023, reverting back to the lottery in 2024. The Raptors realized they needed to shake things up, which led to them trading Siakam to the Indiana Pacers for Bruce Brown, Jordan Nwora, Kira Lewis Jr., and three first-round picks.

2025: Brandon Ingram Acquired by Raptors

The main player with substance in that trade with the Pacers was Brown, as he was mainly there to match salaries after he earned a two-year, $45 million contract following his championship run with the Denver Nuggets in 2023. Brown didn't fit like a glove in Toronto, which led to the Raptors flipping him in another trade a year later to the New Orleans Pelicans, along with Kelly Olynyk and future draft capital, for Brandon Ingram.

Ingram was coming off an injury, but he was healthy for the 2025-26 campaign, when he returned to All-Star form and led the Raptors to their first playoff appearance in four years.

Ingram was strong for the Raptors throughout most of the regular season, but he struggled in the team's playoff series against the Cleveland Cavaliers and suffered an injury that held him out for the latter half of the series. Ingram's value definitely improved throughout his time in Toronto, but it wasn't enough to make the Raptors a true title contender.

2026: It Becomes Full Circle ... Almost

After a long offseason saga, the Raptors were finally able to finalize the deal that would send Ingram to the Clippers, along with Gradey Dick and multiple first-round picks, for Leonard. It's a saga, a story that has lasted nearly a decade, but the Raptors have been very meticulous about which moves to make and the timing of those trades.

If getting Leonard back to Toronto was the goal, then they certainly accomplished that, but that isn't the final destination. The Raptors are still looking for that second championship, whether it comes with Leonard or not. If they are able to hoist the Larry O'Brien Trophy with Leonard on board, then that's when it will truly become a full-circle moment.

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