The Raptors experienced a familiar ending in 2017: another year, another playoff loss at the hands of LeBron James. Despite a 59-win season, home-court advantage and the Cavs coming off a grueling seven-game series, the Raptors got embarrassed in a sweep.

General Manager Masai Ujiri decided to make major moves, and the fallout could result in a tumultuous season for Toronto. After the most successful era in Raptors’ history, Toronto’s future is murky.

DeMar DeRozan arrived in Toronto during a rebuild in 2009. The USC star showed his prowess as scorer during his first four seasons, but the Raptors were unable to get to the postseason. Public interest was lukewarm: the team ranked 14^th, 19^th, 17^th and 13^th in average attendance during those seasons.

Ujiri was brought in to change the trajectory of the franchise. Head coach Dwane Casey was already in place and Ujiri believed he had a winning combination in Kyle Lowry and DeRozan. The Raptors exploded, making the playoffs in five straight seasons. Toronto soared from 10^th in attendance in 2013-14 to fourth during a franchise record 59-win campaign in 2017-18. It seemed the Raptors were finally poised to break through the Eastern Conference and bring the Finals to Canada.

Instead, James and the Cavaliers bounced the Raptors from the postseason for the third straight season. Casey, who would go on to be named Coach of the Year, was fired and replaced by assistant Nick Nurse. In a far more seismic move, DeRozan was sent to San Antonio as part of a package for Kawhi Leonard. Two of the three people most responsible for Toronto’s success on the court were suddenly pushed out.

Meanwhile, James, a seemingly permanent thorn in Toronto’s side, chose to sign with the Lakers in free agency.

The Raptors could and probably should have waited on James’ decision before making the changes they did. If Ujiri believed James was the lone hurdle to playoff success, his departure from the conference opened up a clear path to the Finals. Casey, who had already modified his schemes, would be able to keep a good thing going with a dynamic backcourt and several young pieces. DeRozan, who added a perimeter shot during the offseason, could’ve had the chance to finish what he and Lowry started.

After the trade, DeRozan said, “I felt like I wasn’t treated, with what I sacrificed for nine years, with the respect I thought I deserved.” Lowry dodged questions about the trade at a USA Basketball camp. Leonard, who had requested to be traded from the Spurs with designs to go to Los Angeles, was reportedly thinking of sitting out the year in Toronto before hitting free agency. Leonard’s health was also in question after he played just nine games in 2017-18.

Any chance of Leonard signing long-term in Toronto likely went out the window with DeRozan’s departure. It’s close to impossible to sell a player on an organization’s culture and commitment to winning while simultaneously dealing a homegrown player largely responsible for that culture and winning.

Lowry, Toronto’s other star, was clearly in a sour mood after his backcourt mate and good friend was dealt. Will that sourness bleed onto the court early in the season? Toronto isn’t committed to Lowry beyond 2019-20 — this situation could get ugly. DeRozan was beloved among the fan base as well. It’s not out of the realm of possibility that Toronto sees its attendance dip this season.

Ujiri could have gone “all-in” on a title effort by keeping DeRozan and dealing a combination of young players and picks for Leonard, but Spurs head coach Gregg Popovich reportedly didn’t want to sit through a rebuild. After making the postseason every year since 1997-98, who can blame him?

However, the package the Spurs received doesn’t push them closer to a title. DeRozan, despite being an All-Star, is a downgrade from Leonard. Jakob Poeltl is a fringe starter. The first-round pick Toronto sent is top-20 protected.

These moves have put the Raptors in an odd position. They are competing for a title and certainly have the talent to get out of the Eastern Conference while attempting to develop the young players they refused to sacrifice in a trade. They are being led by a first-year head coach and will almost surely see Leonard bolt in free agency after one year. Lowry and Serge Ibaka come off the books in 2019-20. Jonas Valanciunas has a player option and could leave. Toronto may be facing a rebuild with its young players in two years. DeRozan’s contract, had the Raptors kept him, would’ve been off the books by this time.

If Ujiri’s idea was to remain competitive while being able to pivot to a rebuild if necessary, there’s reason to believe he didn’t need to trade DeRozan at all. In an attempt to shake things up, Ujiri may have inadvertently created a fractured locker room and a cloud of uncertainty.

If Leonard is healthy and gives 100 percent, Toronto will be a contender to get out of the Eastern Conference. With James out West, the Raptors won’t be phased mentally in the postseason and should be able to match up with the Celtics talent-wise. But if Toronto’s young players don’t develop as expected, the franchise’s most successful era on the court could end with a massive dud and all the blame will fall on Ujiri’s shoulders.