Players from Raptors’ championship core tried recruiting Damian Lillard following Kawhi Leonard’s departure 4 years ago

As reports regarding the Toronto Raptors' interest in Damian Lillard surface, a new rumor has come to light linking the two parties. Toronto reportedly could've been a landing spot for Lillard four years ago as their next superstar following then-finals MVP Kawhi Leonard's departure.

Several Raptors players tried recruiting Lillard, according to the team's beat writer, Michael Grange. Toronto was coming off a championship anchored by Leonard, who had left to join his hometown franchise, LA Clippers, in free agency.

"Not long after the Raptors won their 2019 championship, some Raptors players reached out to Lillard about the possibility of joining forces in the post-Leonard era and were instantly rebuffed," wrote Grange (via Basketball on X).

That move obviously never came to fruition, with Lillard being adamant about winning a championship with Portland. Meanwhile, the Raptors continued believing in their core around Leonard to deliver results and defend their crown and didn't pursue any other star.

Toronto did well in the regular season, finishing with a 53-19 record after the season got cut short due to the Covid-19 pandemic. They played in the 'Orlando Bubble' in the playoffs but could only make it as far as the conference semis, where they lost in seven games to the Boston Celtics.

Meanwhile, Damian Lillard's Trail Blazers exited the playoffs in round one following a 4-1 loss to the eventual champions, LA Lakers.

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Raptors making their presence felt in Damian Lillard sweepstakes

After four quiet offseasons since Kawhi Leonard's departure, the Toronto Raptors are looking to make a big-name addition. They are among the frontrunners to land Damian Lillard. Toronto has some of the best assets to make a deal happen.

They could engage with multiple teams and get a trade done. According to Raptors' beat Michael Grange, Masai Ujiri and his front office are confident of outbidding rival suitors.

"By all accounts, the Raptors seem at least reasonably confident they can maneuver their way to the front of the line, past the Miami Heat — Lillard’s preferred destination — and ahead of a team such as the Brooklyn Nets, who have the draft picks to get something done if Portland is open to taking on the last two years of Ben Simmons’ contract," wrote Grange.

The Raptors may hold better chances of landing Damian Lillard due to their assets. However, the player reportedly doesn't want the trade. According to Miami Heat's beat reporter Ethan Skolnick, a reporter close to Lillard's agent said he might make things 'ugly' if Portland moves him to Toronto.

"Toronto is a place that Dame would make it ugly," reported Solnick. "He didn’t mention Chicago. He didn’t mention any other teams. He mentioned Toronto as a place that Dame would make it ugly."

Several reporters, including The Atheltic's Shams Charania, have claimed Lillard has made his intentions clear to the Trail Blazers that he intends to play for the Heat only. However, Portland will likely want to maximize their returns on their best player to embark on their rebuild.

As it stands, they could make a trade that helps their case, not Damian Lillard's. That said, there is a fair chance that the All-Star guard might end up with the Raptors against his wish of a move to Miami.