The Raptors’ future will be defined in an off-season of uncertainty. This is where Masai Ujiri and Bobby Webster earn their money

The Raptors are facing an off-season like no other. They have a handful of free agents to decide on, an uncertain NBA financial picture and a first-round pick in the draft. This is the last of a six-part series looking at the decisions and options that lie ahead:

For Masai Ujiri and Bobby Webster, the NBA summer is a well-scripted time with little variation year to year.

The season ends some time around the middle of June, the draft is a week or two after, free-agent discussions can officially begin July 1 and players can be signed and roster holes filled about five or six days later.

There’s summer league that takes a huge chunk of July, some rest and a chance to catch your breath in August, and then the hard work of player development begins in earnest.

It’s when team presidents and general managers earn their money, cement their reputations and set themselves up for the season to come.

Well, here we are, nearing the end of September in this strangest of seasons and how are things looking?

Well, Ujiri and Webster think the draft might be held on Nov. 18, but that’s a moving target. They have no real clue when free agency will start. Summer League is dead and gone, and they don’t have any indication yet of how much money they’ll have in the salary-cap pot, nor when they might be able to start group workouts and training camp — for a 2021 season that could start in January and might not get going until February.

Other than that, things are peachy for the men in charge of the Raptors.

“You have the challenges and we have to face them,” Ujiri said. “We don’t know what the cap numbers are. We have to figure out how we manoeuvre, where we keep our cap space for the future and for that year, ’21 (when one of the most lucrative free-agent classes ever may be on the market).

“We have to address that in some kind of way. We are going to speak to all the agents when the time is right, and speak to all the players when it is right, and we’ll try and figure this out the best way we can.”

Yes, there are challenges, but it’s nothing that we haven’t dealt with in the past.”

But the truth is, they’ve never had to deal with circumstances like this, even their own.

Both of them have contracts that run out at the end of next season and the longer they dither in re-signing, the more questions will linger about the long-term future. It’s not going to affect how they do their jobs — they’re too professional and competitive for that — but it does hang over the organization.

Ujiri did say they are “close” to a new deal for Webster, but that was a week ago and nothing has been announced, while he’s downplayed his own contractual status, saying he’d take care of others in senior management before thinking about himself.

Whether there are opportunities even bigger than running a franchise that might interest him is unknown, and Webster, while a highly respected general manager, isn’t seeing a market with a whole lot of job promotions available to him right now.

“We are getting there,” Ujiri said of negotiations on a new deal for Webster. “It is a priority for me to get to our leadership team and take care of the team and the organization in general, so we’re close.”

The jobs at hand — despite the uncertain timing — are clear cut and well-documented.

There are three key free agents — Fred VanVleet, Marc Gasol and Serge Ibaka — and dealing with them will be the first task. A long-term contract for VanVleet and one-year deals with either of the other two should preserve salary-cap room for 2021 and address critical present needs, but the only hint Ujiri would give is that he considers everyone a priority.

“It’s all communication and how we relate to our players,” Ujiri said. “We are very confident with our culture and, yes, Fred is a priority, our bigs are a priority — Serge had an incredible run, Marc Gasol brings so much to our organization — and we have our young players coming up with Chris Boucher. Rondae (Hollis-Jefferson), too, is a free agent and he found a niche with our organization.

“That’s what our jobs are. We have to face them square on, and we will deal with them as we come, as we have in the past.

“We have to really attack this head on, and we know where their game is. We know how much they can improve. We try to project that as much as we can. We know where they have come from too, because we have gone through all these struggles with all these guys and we mutually appreciate that.”

The draft is a unique situation for the Raptors, who haven’t had a first-round pick of their own since they took OG Anunoby at No. 23 in 2017.

Like every NBA team, their in-person scouting plans came to a screeching halt in early March, and they’ve been hamstrung in their preparations since. There have been video workout sessions they can view and cyber meetings to learn something about the personalities of possible selections, but no face-to-face interaction.

The NBA has set up a virtual scouting combine that includes some in-person workouts with trainers through October, but how much value that would have in debatable. And whether the Raptors would even keep their pick — No. 29 — is also uncertain. Using it in a trade package might make sense but, again, the unknown financial situation makes that difficult.

Most draft-night trades are centred on current players or contingent on the following season’s salary cap and until those things are clear, teams are limited in what they can do.

But all of that pales in comparison with the simple fact that no one knows when — or officially if — a 2021 season is in the picture. Commissioner Adam Silver said this week that he doesn’t expect games to be played until January, and the league’s dream is to have 30 teams playing in their home arenas. No one knows if that will ultimately be possible or how many people might be in whatever arenas they use.

“That’s one thing I am praying and hoping (for), just like everyone else, that we can get back to normal,” Ujiri said. “I want to play with fans. I want us to figure this out. This pandemic is serious. We know there could be a second wave coming … for me, it is a priority for us to figure out how to get our fans involved and how to figure this out going forward.

“I know the NBA is grinding on this as much as they possibly can. Yes, I continue to be optimistic.”