Striking similarities between Kawhi Leonard and Damian Lillard’s situations emerge amid Raptors interest in latter 

Damian Lillard could end up playing for the Toronto Raptors. Recent reports have indicated the Eastern Conference franchise may have significant interest in the veteran guard. However, Lillard is rumored to have made his feelings on a potential trade to Toronto abundantly clear.

With all the noise surrounding Lillard's desire to play for the Miami Heat and his tenuous situation in Portland, NBA fans are starting to draw comparisons with Kawhi Leonard. The former San Antonio Spurs star was in an eerily similar situation before he was traded to the Raptors, where he won a championship later that season.

Leonard's situation was slightly different, though. He had been sidelined with an injury and was unhappy with how the organization had handled his recovery. Lillard wants to win and doesn't see that opportunity arising with Portland, despite his best efforts to remain loyal and patient.

The Heat remains at the top of Lillard's desired destinations. Yet, with two years remaining on his current contract and a further two-year extension after that, Lillard doesn't hold much negotiating power regarding which team acquires him. With so much money on the table, it's unlikely the seven-time All-Star will refuse to play.

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Raptors players previously tried to recruit Lillard

Lillard has had talks with the Raptors franchise before. However, the veteran guard resisted the urge to join a team coming fresh off a championship win, as he continued to stay loyal to Portland.

According to SportsNet's Michael Grange, members of the Toronto Raptors 2019 championship team tried to recruit Lillard to the franchise but were unable to convince him to make the switch.

"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).

Lillard desires to compete for championships. Toronto is currently straddling two timelines and would need to part with a large number of assets to acquire the superstar guard. As such, there's no guarantee the Raptors could offer Lillard the high level of success he's searching for. If anything, it would potentially be a lateral move.

Portland will continue searching for the best trade package available. Lillard will keep applying pressure to be traded to the Miami Heat. Unless a multi-team trade can be figured out, Portland will likely do what's in the best interest of their franchise. Still, the Trail Blazers will need to be wary of the optics. After all, Lillard has remained loyal far longer than he should have.

The trade saga will continue to rumble on until someone firms up their interest and takes things past the discussion stage. Until then, Lillard remains with the Portland Trail Blazers and could potentially begin the season with the franchise he's represented his entire career.