Raptors face three different paths as important off-season looms

The Ringer's Kevin O'Connor explains whether the Toronto Raptors are a fit for Ben Simmons and what it might take to get him.

The NBA Draft is Thursday, free agency opens on Monday and the Toronto Raptors are in limbo.

Which isn’t automatically a bad place, but by definition it’s an uncertain one and in an industry as systematically chaotic as professional basketball -- where everything is geared to pull teams apart rather than keep them together -- an added dose of ‘what happens next’ isn’t necessarily positive, either.

The answers as to what direction the Raptors are heading in will come in the space of a week. By then the draft will have come and gone and we should have a clearer picture of what the future holds for Kyle Lowry.

Oh, and we may even find out what the official status of Raptors president Masai Ujiri is, or when it might be resolved.

According to multiple sources I have spoken in recent weeks, Ujiri is conducting business during the most important period on the NBA calendar like he’s the once-and-future president of the Raptors, but there’s been no confirmation from the team that he’s signed a new contract or when he will.

There’s no underground buzz about what his other options are, so as has been reported consistently here since before the 2020-21 season began, the likeliest scenario remains that Ujiri is back with the team that he’s been so closely identified with for a 10th season.

“I’d be shocked if he’s not back,” said one source I spoke with this week, echoing the views of several others.

But the questions Ujiri and/or general manager Bobby Webster need to answer are looming, significant, potentially inter-related.

The biggest one is what type of team do the Raptors want to be when they -- hopefully -- return to Scotiabank Arena for the 2021-22 season, for which training camp is barely two months away from opening.

If the goal is to pick up where they left off the last time they played there -- remember those pre-Pandemic times, back in March of 2019 when the Raptors were on their way to second-best regular-season record in the NBA even without Kawhi Leonard and Danny Green?

If that’s the case and there’s still a belief that the essence of the current club can return to contender status in the East, then things aren’t that complicated at all: Re-sign Lowry and draft the best player they can with the No. 4 pick, while hoping it’s Gonzaga guard Jalen Suggs or multi-skilled USC big man Evan Mobley.

If they were really determined to go all-in on a 2019-20 run back, they could even explore trade packages including the highly valued fourth pick, but that’s unlikely.

At the other end of the scale is punting on the current configuration of the roster, an acknowledgement that last season -- even with the relocation to Tampa and all accompanying disruption -- wasn’t entirely anomalous. Not that the Raptors weren’t better than their 27-45 record would suggest, but that they aren’t all that good either -- certainly not ‘contend for a title good.’ In that case maybe it is time to rebuild, or reset or reload or whatever you want to call it.

In that scenario the Raptors still draft the best player available at No. 4 or try a little harder to move up to the No. 3 spot if that’s what it takes to guarantee getting the player they want.

Lowry would not be back, of course, but it makes sense Toronto would listen carefully to offers for Pascal Siakam, such as they are.

I can’t confirm that the Golden State Warriors would make a deal for the 27-year-old former all-star, but if you’re a team trying to rebuild on the fly and you can grab James Wiseman -- the No. 2 pick in the 2020 draft, the No. 7 pick in the current draft and Andrew Wiggins (for salary matching purposes, though the 26-year-old might yet have some upside), the Raptors would be obligated to listen.

The third possibility -- and maybe the most likely one -- is the Raptors try to thread the needle between winning now and building for a distant future.

That’s why there’s buzz around the Raptors getting on Sixers star Ben Simmons being available. In an ideal world, Toronto can get something done involving Lowry and a sign-and-trade, but as much as adding a 24-year-old All-NBA player, the Raptors aren’t about to sell off their young core to do it.

Again, Lowry is still likely to move on -- signing a 35-year-old point guard for $30 million on a two-year deal, let alone one that has a third year guaranteed, doesn’t make a load of sense if the goal is to give your existing young core room to grow. It was hard enough to find minutes for Malachi Flynn last season, so drafting Suggs while paying Lowry and Fred VanVleet makes little sense.

But the Raptors would have the cap space to sign a big man in free agency, with Richaun Holmes of Sacramento, Kelly Olynyk -- who impressed finishing the season well in Houston -- and maybe even Cavaliers restricted free agent Jarrett Allen -- just 23 and as he heads into his fifth season -- as possible targets. Depending on the price there might even be room to also sign Khem Birch, who the Raptors have generally looked at as a capable backup.

But barring adding Simmons, would their existing core (minus Lowry), the addition of the fourth pick and getting some help at centre in free agency be enough to vault the Raptors back into contender status?

Contending might be a stretch, but being young, flexible, and respectable is right there, and from that point taking the leap to contender doesn’t seem so far-fetched, especially if who they draft at No. 4 ends up having star potential.

Which direction the Raptors end up heading will make for great theatre, and the curtain is about to rise.

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