Fresh off their first championship in franchise history, the Toronto Raptors find themselves in an interesting position heading into the 2019-20 campaign. Their best player, Kawhi Leonard, is gone, and with his departure comes more questions than answers heading into next season. It also means a number of young players are preparing themselves to step into expanded roles and prove their worth to Raptors’ brass.

The Raptors roster will be significantly different next season, although the core of the team remains the same. Kyle Lowry (33), Serge Ibaka (29), and Marc Gasol (34) are all entering the latter stages of their respective careers and all find themselves on expiring contracts, meaning they could be moved before the season is over. The young core of the team remains the same, and the keys to the franchise will be handed over to the likes of Pascal Siakam, Fred VanVleet, OG Anunoby, and whoever else who proves their long-term worth.

The Raptors replaced Leonard and Green with defensive-studs Stanley Johnson and Rondae Hollis-Jefferson, high draft picks who materialized with their former teams. They also signed EuroLeague sharpshooter Matt Thomas, undrafted combo-guard Terence Davis, and the 59th pick in the draft, the raw but athletic forward Dewan Hernandez.

The Raptors are in an uncommon situation for NBA champions: ESPN projects them to win just 45.5 games and finish fifth in the Eastern Conference behind the Orlando Magic. It makes some sense given that the Raptors lost their best player this offseason, but the Raptors have proved doubters wrong time and again, consistently overperforming since Masai Ujiri took over in 2013.

Still, there are more questions than answers for the Raptors. Ones about how the front office wants to build for the future, how much the franchise values Siakam, which young players will succeed in expanded roles, whether or not the team can compete with the top of the East, and how competitive they need to be in order for Ujiri to hold onto his veterans for a playoff run.

Here are the six most interesting storylines heading into next season:

#1 – Siakam-Watch

Pascal Siakam, the 25-year-old Cameroonian power forward who emerged as a breakout star last season — earning him the Most Improved Player award — is entering the final season of his rookie-scale contract (making just $2.35 million) and is currently eligible for an extension.

The Raptors have until the start of the regular season to sign Siakam. If they don’t get an extension done, which looks like a real possibility as training camp approaches, the two parties will be forced to play out the season before contract negotiations can pick up again.

Blake Murphy wrote an excellent guide explaining Siakam’s contract situation here, but the basic for-and-against arguments are clear: Signing Siakam now would give the player increased job security and could come at a discount for the organization (compared to waiting until next summer), but waiting gives the Raptors more time to evaluate Siakam as a primary option as well as increased cap flexibility to sign free agents in 2020. If Siakam remains unsigned, the Raptors are betting against him growing upset with the franchise (like how Kristaps Porziņģis reportedly grew upset with the New York Knicks for not immediately extending him), and it’s a reasonable bet considering his positive relationship with Ujiri and how the Raptors helped develop his skills.

What we do know is that no matter how the contract negotiations go this summer, the Raptors plan on keeping Siakam in the fold long-term. Whether or not he will be the player they build around is the question.

Despite being an older prospect at 25, Siakam started playing basketball at age the mature age of 15, and has made a steady improvement every year in his career. He is also the type of versatile player modern NBA franchises covet: He can play any forward position, legitimately guard one through five, and he doesn’t need the ball in his hands to succeed. He also helped lead the Raptors to a championship as the second option on most nights, taking on some of the best defenders in the world (Draymond Green and Joel Embiid) while scoring 19.0 points per game on 47.0 percent shooting throughout the playoffs.

https://www.youtube.com/watch?v=tBuGQ1X_7ns

Still, Siakam has never been a primary option in the NBA — last season he wasn’t even sure he would be in the starting lineup. Siakam also shot just 27.9 percent from three in the playoffs and has never been an efficient shooter from beyond the arc. How far his jump shot and playmaking abilities come along will be key in determining whether the Raptors want to build around Siakam as their primary option going forward.

It would be nice to see Siakam develop a reliable jump shot from different places on the floor, but to me, Siakam’s best bet at making another leap forward next year comes on the other end of the floor. Last season’s MVP Giannis Antetokounmpo — who Siakam’s game is very similar to — proved that you can be among the league’s best without an elite jumper as long as your two-way game prevails. Siakam has the potential to make an All-Defensive team (he received 24 second-team votes last season) and maybe even win a Defensive Player of the Year award one day. Next season will be his biggest test yet as he looks to carry an elite NBA defense without Leonard.

just gonna leave this here pic.twitter.com/59WhnooY50 — William Lou (@william_lou) August 19, 2019

The 2019-20 season is a test for Siakam and for the organization. It will be fascinating to see how Siakam handles being the primary option and if he proves to be a player the franchise can build around. Simultaneously, how the organization handles his contract — that is, whether or not they hand him something close to the five-year max before or after the season — will determine how much the franchise values him long-term.

#2 – The Rest of the Young Core

Siakam isn’t the only young player entering the final season of his contract. Fred VanVleet (25), another crucial contributor in the Raptors title run, is entering the final year of a two-year, $18 million contract he signed in 2018. VanVleet, along with the rest of the Raptors young core including OG Anunoby (22) and Norman Powell (26), will enter the 2019-20 season with added responsibility and more than ever to prove. Namely, who can establish themselves as an irreplaceable player going forward?

VanVleet had an up-and-down 2018-19 season due to minor injuries getting in the way of things, but his unbelievable playoff run — particularly the final two series’ — proved that he was smart to once again bet on himself with a short contract last offseason. VanVleet averaged 8 points on 39/39/77 shooting in the postseason but truly proved his worth in the final two rounds where he went 14-for-17 on 3-pointers in games 4, 5, and 6 of the Eastern Conference finals and then locked down Steph Curry while hitting some of the biggest shots of his career against the Warriors.

VanVleet has one more season to prove to the Raptors that he is worth a long-term deal, but in order to get the most money possible, he will need to prove that he can be a starting guard in the future as Lowry ages into his mid-thirties. One interesting idea that was discussed on the Raptors Over Everything podcast is VanVleet as a potential two guard who defends point guards since he thrives off the ball. Regardless, VanVleet will likely start at least twenty games next season, both at point guard and shooting guard, and will have more responsibility than ever on the offensive end. Assuming he plays with the bench most of the time, he will be the primary facilitator with the second unit as well as a key floor spacer. The key for VanVleet will be figuring out how to play against bigger teams that defend him with length as Philadelphia did in the playoffs when he couldn’t stay on the floor. He needs to improve his first step and become more confident in his pull-up jumper.

As for the starting shooting guard position, Norman Powell has an opportunity to step into that role for the first time in his career now that DeMar DeRozan and Green are gone. Powell quietly had the most efficient year of his career last season, shooting 48/40/83 in a simplified role, playing just 18.8 minutes off the bench. However, the question is whether or not Powell can remain efficient in an expanded role, something he has had little opportunity to show in his career (Powell, to me, is the Raptors biggest x-factor next season, which I will explore in a follow-up piece next week). Powell will have plenty of opportunities to shoot, especially if he steps into a starting unit that lacks pure scorers, but he will have to do it efficiently if he wants to prove to the Raptors that he should be in their plans going forward. In fact, this could be a make-or-break year for Powell, who is entering his fifth season with the Raptors but is yet to prove he is an irreplaceable piece of their core moving forward.

And then there’s OG Anunoby. The 22-year-old small forward basically lost last season to injuries and personal issues but just one year ago he was a rookie starter tasked with guarding LeBron James in the playoffs. Anunoby figures to step into the starting small forward spot left vacant by Leonard, but he has struggled to create his own shot throughout his young career and is more efficient as a catch-and-shoot threat. With Leonard and Green gone, there will be plenty of shots up for grabs, and Anunoby will need to be aggressive in getting his. We already know he can defend all five positions at an elite level, but the next step in his progression is the opposite of Siakam’s: He needs to become a more well-rounded offensive player and a better facilitator (he has averaged just 0.7 assists in each of his two seasons). Still, there is a lot to like about Anunoby and he figures to at the very least develop into an effective 3-and-D wing sooner than later.

#3 – Top of the East

While the Raptors project to be a solid team next season, the loss of Leonard will be more noticeable against the leagues’ best teams. Whereas last season the Raptors had the best player on the court in almost every game (or at least the 60 Leonard played), this season will be different as the top teams in the East — Milwaukee, Boston, and Philadelphia — each have superstars better than Pascal Siakam, the Raptors best player.

How much will it matter? In a playoff series, it could be significant. However, as the Raptors have shown time and again, it is possible to win by committee. A combination of roster versatility, team chemistry, and defensive aptitude could allow this Raptors team to compete with the top of the East, no matter who the best player on the floor is. In the regular season at least.

This is what Ujiri will monitor as the season goes along: Can his team can compete with the best teams in the East, and if so, is that going to be sustainable in a playoff series? If he thinks the answer is no, he will likely look to sell at least one of his veterans at the trade deadline. However, If the answer is yes, he may try to defend the title.

#4 – The Selling Line

So where is the selling line?

Ujiri has made it clear that he will give the Raptors a chance until the trade deadline to see how competitive the team is, but where exactly is the line determining whether or not the Raptors will be sellers at the deadline? That, my friends, is the golden question.

It could be that Ujiri wants to trade at least one of his expiring veterans — Lowry, Ibaka, and Gasol — no matter where the Raptors stand, and that he will use the first half of the season to try to boost their value and determine what he wants in return. More likely, though, Ujiri will constantly monitor the market for his three veterans and only make a deal if the return is worth it and the outgoing player has become more-or-less expendable.

For that reason, barring a huge offer, I find it unlikely that Lowry will be traded before the end of the season. The Raptors just aren’t deep enough at the point guard position and he is truly the engine that makes the team go. However, with Ibaka and Gasol making a combined $49 million next season and playing the same position in a loaded frontcourt (with several young players competing for minutes), it would make sense that at least one of them is traded in exchange for pieces that will help the Raptors moving forward.

The only way I see none of the veterans getting moved is if the Raptors outperform all expectations and prove that they are once again the best team in the East.

#5 – New Faces

If the Raptors are going to compete with the best next season, they are going to have to win by committee and make up for their lack of talent with a darn good bench (not unlike what they did from 2013-2018). And their bench will likely be filled with a lot of new faces. Assuming Powell starts at the two and Anunoby at the three, which seems to me the best-case scenario and also the most likely, the bench will be made up of VanVleet, Ibaka, Johnson, Hollis-Jefferson, Davis, Thomas, Chris Boucher, Malcolm Miller and Patrick McCaw.

Defensively, the Raptors bench should be able to hold off opposing benches fairly consistently. But on the offensive side of the floor, the bench severely lacks shooting and proven scorers. One of the new faces is going to have to make a leap on that side of the floor if the Raptors bench is going to be competitive. Although that might sound like a lot to ask for, Ujiri has constructed a young bench filled with potential and opportunity, and the Raptors system has been known to get the most out of incomplete players.

If one or more of the new faces can make the most of their opportunity with the Raptors, the bench could be legitimate next season.

#6 – Toronto as a free agent destination

At the top, I stated that there are more questions than answers heading into next season. While that remains true, one answer is evident: The Raptors want to position themselves to land marquee free agents in the near future.

I recently wrote about how increased player empowerment could affect the Raptors going forward, and one of the points I made was that even though the Raptors had a bad offseason losing Leonard, they still positioned themselves as an attractive market for future free agents. They are once again one piece away from being championship contenders, and if they are going to get that piece in free agency rather than through the trade market or the draft, they better hope their young core establishes themselves even further as one of the best in the league and that Siakam establishes himself as a legitimate star. The Raptors core clearly enjoys playing together as evidenced by how many of them are training together this summer, which is a testament to the culture the Raptors have developed; a culture that should be attractive to free agents. Although the free-agent class of 2020 isn’t as special as this past summer’s, there are still plenty of helpful players entering free agency — many of them restricted — and the Raptors will pursue them aggressively.

Another thing that will be interesting to monitor is how the fan base reacts to a less competitive team. Last season we saw Toronto support the Raptors in the biggest way possible, but without Leonard and with little chance of a title, will the fans still show the same support? Or do Torontonians only support winning teams (outside of the Maple Leafs, who are outliers), something the Blue Jays might argue? My bet is that Raptors fandom is real and growing and that most fans will stick around through thick and thin, but it will be interesting to monitor nonetheless.

Training camp opens on September 28th at Laval University in Quebec City.