Masai Ujiri is still trying to repair relationship with DeMar DeRozan

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Toronto Raptors (Photo by Ezra Shaw/Getty Images)

It's been almost two years since Masai Ujrir traded away DeMar DeRozan to acquire Kawhi Leonard. As it stands, his relationship with DeRozan is still a work in progress.

Time flies in life, and time flies in basketball. It's hard to believe that it's been almost two years since the Toronto Raptors traded away DeMar DeRozan in the summer of 2018 to acquire a superstar in Kawhi Leonard - again, time flies by.

DeRozan spent nine ultra-successful seasons with the Raptors, who drafted him with the ninth overall pick in the 2009 NBA Draft, becoming the franchises all-time leader in points scored, games played, and free throws made, among other records. Frankly, DeRozan's status as one of the greatest players in Raptors history is well-earned, even if the position of where he ranks is up for debate.

That's why it came as such a shock when the Raptors made the emotionally difficult, but franchise-bettering, move to trade for the disgruntled Kawhi Leonard following the 2017-18 season. Leonard felt disenfranchised with how the San Antonio Spurs had handled his lingering quad injury at wanted out - and so the Raptors came calling.

The rest, of course, is history. The Raptors went on to win their first-ever NBA championship in the 2018-19 season with Kawhi Leonard playing a pivotal role, averaging 30.5 points, 9.1 rebounds, and 3.9 assists throughout the postseason and he was justifiably named as the Finals MVP following the Raptors 4-2 series win against the Golden State Warriors.

While everything was hunky-dory for the Raptors, it was clear that DeRozan was hurt by Ujiri's decision to trade him to the San Antonio Spurs. So much so, that Masai Ujiri is still trying to repair the broken relationship with his former franchise player.

In an NBA Twitter interview with TNT's Ernie Johnson, Ujiri was perfectly candid when recounting the moments leading up to him telling DeRozan he was to be traded:

"DeMar, I was in the hotel in Kenya, and I walked around that hotel at 4 a.m., 5 a.m., for a couple hours, trying to gather up enough strength and courage to make this phone call. I will never forget it…" Ujiri said.

As much as it was disappointing news for DeRozan, it is obvious that making the decision was also one that Ujiri struggled to make - if mostly on an emotional level. DeRozan was there before Ujiri had arrived in Toronto and was an integral part of the culture that brought the Raptors their most successful period in franchise history.

Making the trade was definitely the correct decision, even if Leonard did only stay in Toronto for one season, but the effects on Ujiri's relationship with DeRozan have certainly, and will likely, take a little longer to repair.

"With DeMar, there is still plenty of work to be done. But, by the grace of God, it will all get better," Ujiri said. "We have to continue to make these decisions that are tough. But that’s the business of basketball and the position that we are in.”

Next: 10 best trades in Toronto Raptors history

Hopefully, the two can salvage some sort of relationship in the future and, who knows? Maybe we'll see DeRozan back in Toronto someday. For now, Ujiri is right: that's business.