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What’s next for the Raptors after the push for Damian Lillard falls short?

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With Damian Lillard in the rear-view mirror and NBA training camps opening in a few days, now is the time for the Raptors front office to decide which path they take – and stick to it. 

Days after ESPN’s Marc J. Spears reported that the Toronto Raptors were frontrunners to land Damian Lillard, the seven-time all-star was traded to the Milwaukee Bucks, once again leaving the Raptors at a crossroads. 

The Bucks acquired Lillard from the Portland Trail Blazers on Sept. 27th as part of a three-team trade with the Phoenix Suns, giving up Jrue Holiday, Grayson Allen, their 2029 first round pick and two pick swaps for the 33-year-old point guard.  

Raptors President Masai Ujiri could have put together a far superior trade package but the risks of him not showing up to training camp for the Raptors, as reported by Shams Charania via The Rally, would have been too risky of a move to part ways with young stars and future assets. 

Instead, Ujiri and company elected to keep the young core of O.G. Anunoby, Scottie Barnes and Gradey Dick in Toronto but still have unfinished business as they decide on the direction that the organization heads this season and beyond. 

The question is clear: Is it time to rebuild around the young core, or do the Raptors keep the championship mindset and add a star to put them back into title contention? 

First and foremost, if the Raptors decide to enter rebuild mode, a decision needs to be made on the future of Pascal Siakam in Toronto. The 29-year-old has one year remaining on his contract before he enters free agency next summer, as there are likely to be many suitors hoping to add the two-time all-star to their team. Siakam, who was drafted and developed by the Raptors, has expressed interest in staying in Toronto as reported by Bleacher Report’s Chris Haynes. The Raptors can use that to their advantage should they decide to resign the power forward. 

However, if the Raptors decide that Siakam isn’t part of their future plans, a trade needs to be imminent to get assets – young players and draft capital – in return. Siakam’s trade value is at its highest coming off a season where he averaged his highest points per game and assists per game in his career. The Raptors could wait to see if his value increases, especially as teams get desperate for a star during the season and if Siakam exceeds his previous performance, but the Cameroonian has dealt with injuries in his career and is one big injury away from plummeting his trade value. 

What the Raptors can’t have is a repeat of the Fred VanVleet situation that unfolded this summer. VanVleet left in free agency for Houston, despite opportunities to trade the point guard for decent assets during the season, resulting in the Raptors getting nothing in return for the all-star’s departure – a lesson that Ujiri and Bobby Webster hopefully learned from. 

O.G. Anunoby, who has one year left on his deal plus a player option for 2024-25 that he’ll likely opt out of, could also become a free agent next summer. It would be ideal – and is most likely – that the Raptors build around Anunoby as one of the centrepieces of their team if they decide to rebuild. The 26-year-old is a defensive workhorse being named to the NBA All-Defensive Second Team in 2022-23 and tallied a league-leading 1.9 steals among qualified players along with 16.8 points per game and five rebounds per game last season. 

Scottie Barnes, the 2021 fourth overall pick, and Gradey Dick, the Raptors’ first round pick this year, will be the focal point with Anunoby if a rebuild does occur, as the trio can grow and develop together under new head coach Darko Rajakovic. The Serbian coach is regarded as one of the best coaches for developing players according to TSN’s Josh Lewenberg, which is an asset if the Raptors roster starts to become younger as pending free agents – Pascal Siakam, Gary Trent Jr., Thaddeous Young and Otto Porter Jr. – get traded for young, up-and-coming players that the Raptors view as the future. 

But the other path at the crossroads is a lot more incentivizing as the reward is far greater, but the risk could be detrimental to the future of the team. 

We already saw the Raptors’ attempt at pursuing this path through their efforts at acquiring Damian Lillard, and given their history of aggressiveness and tenacity, it wouldn’t be surprising if the Raptors are interested when another big name is available for a trade. 

Obviously, trading for a star could work, as it led to the Raptors parading down University Avenue in downtown Toronto after winning the 2019 NBA Championship after a gutsy trade for Kawhi Leonard helped kickstart that feat. 

But it may not work. Just ask the Brooklyn Nets, who traded five players and seven picks for James Harden, who is not on their team anymore. 

The NBA is an ugly place for superstar loyalty as trading numerous picks and players for one or two guys might be too much to gamble. Especially in the super team era, the haul needs to be enough to overcome super teams like the Milwaukee Bucks, Boston Celtics, Golden State Warriors, Phoenix Suns and others, or those assets were essentially flushed down the toilet. 

For the Raptors, they need to internally decide in the next few days and weeks which direction they take, as mediocrity does no good, present or future, in the NBA and North American sports. 

The Raptors open the regular season at home against the Minnesota Timberwolves on Wednesday, Oct. 25th and the complete Raptors schedule can be found here. 

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