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Is one of Jose Calderon or Kyle Lowry headed for Boston?

It was supposed to be simple. Steve Nash was supposed to sign with Toronto, finish his career in a Canadian city and lead the Raptors back to basketball relevance and hopefully a few playoff series'. But when he chose to sign in Los Angeles instead this past summer, Raptors general manager Bryan Colangelo was forced to go with Plan B at point guard, which turned out to be Kyle Lowry.

A 26-year-old with all-star potential, Lowry appeared to be an ideal pick up for a franchise that was looking to build towards success and it didn’t take long for many to buy into what he had to offer on the floor. He averaged 23.6 points, seven assists and 7.3 rebounds in his first three starts of the season. But as the team struggled to win games, many began to point out the flaws and deficiencies in Lowry’s play including his injury issues, which forced him to miss 13 of the Raptors first 29 games of the season, and his selfishness on the floor. Lowry was criticized for trying to do too much and not creating enough opportunities for his teammates.

And now 44 games into the Raptors season, Calderon has earned back his starting job and Lowry has been relegated to a backup role. With Calderon leading the offense the Raptors are nearly a .500 team and the 31 year olds impressive play has some in the media seriously considering whether Calderon is a better fit than Lowry for the team’s current makeup.

Zach Lowe wrote in a story for Grantland.com entitled, “Basketball decisions: Should the Raptors keep Jose Calderon or Kyle Lowry?’

It’s clear that Casey prefers Calderon’s pass-first style of play for now, even as he pushes Lowry to embrace his aggression and denies he’s had any of the “coachability” issues that dogged Lowry in other places. “We haven’t had any of that here,” Casey told Grantland before the Raptors’ loss in Brooklyn on Tuesday. “And Kyle’s edge is what makes him a great player.”

Both Casey and Raptors GM Bryan Colangelo are pleased with how supportive Lowry has been of Calderon — screaming encouragement from the bench and even mock-cooling Calderon with a towel during a hot streak last weekend against Milwaukee. "Kyle has been through something like this in other places, and the outcome wasn't good for anyone," Colangelo says. "He has done it right this time. Almost to a fault, he has done exactly what the coaches have asked him to do."

But Casey has said repeatedly that Lowry needs to find more balance in his game between passing and shooting, between rushing and pausing to see what openings might emerge for teammates. “That’s the Kyle everyone is looking for,” Casey said after Tuesday’s loss, when Lowry exploded for 21 much-needed points trying to lead a comeback on a badly sprained ankle. “We need him to be aggressive, but still make the right basketball decisions.”

While Lowe infers near the end of his story that he’d personally probably stick with Lowry because he’s young and still has time to grow where as Calderon has peaked at this point in his career, the idea that the Raptors would even think to keep Calderon over Lowry would have been seen as nonsensical to say the least at the beginning of this season.

And the recent injury to Boston Celtics star point guard Rajon Rondo has the Raptors PG situation drawing interest once again. Rondo suffered a season-ending ACL injury over the weekend and without a reliable backup Marc Stein of ESPN believes that the Celtics have interest in Lowry.

The question then becomes whether or not the Celtics have the type of young assets that might be able to sway the Raptors into making that kind of trade.

Colangelo and the rest of the team’s management will have to think long and hard before moving one of their two point guards especially with the Raptors still very much in reach of the eighth seed in the Eastern Conference. But with the trade deadline only weeks away the clock is beginning to tick. A decision will have to be made soon.