Raptors Reset: Key decisions, dates and debates for the offseason ahead

“Then that’ll be that, won’t let you ever look back. For her I’ll cut all my players, mess up my salary cap.” – Wale

You’re going to hear a lot of talk about how this is the longest break in recent years. And it’s true. Not since 2013 have I had to wait this long between the end of a Toronto Raptors season and the beginning of the New Japan Pro Wrestling G1 Climax tournament.

Oh, and the Raptors have a fairly long offseason ahead, too.

This is the first time the Raptors have missed the playoffs in eight years. With that comes more time to rest, rejuvenate and recalibrate for a massive offseason ahead. If you’re the front office, you have more than two months before the draft, and a few days longer before free agency. If you’re a player, you have 19 weeks before training camps open, if they open on the league’s pre-pandemic calendar. (For comparison, they had 12, 15, 20, 20 and 17 weeks the last five offseasons.)

As always, there’s plenty to sort through as the Raptors figure out where they’re going next year. They have to decide how to utilize a lottery pick, something that’s pretty unfamiliar to this regime. They have to decide a course of action with Kyle Lowry, and within that is a decision on operating as an above-cap or below-cap team. They have seven non-guaranteed contracts, two restricted free agents and three unrestricted ones. Their head coach and multiple players also have Olympic qualifying and/or the Olympics to focus on. With the pieces that are locked up entering their early prime years and cap space likely to be at a premium in future seasons, the leverage here seems immense.

To say there is a lot of content coming covering all of those decisions is an understatement. The spreadsheets floweth over. Today, we preface that work with our annual reset so we know where we’re going and what checkpoints lie ahead.

Next week, I’ll roll out my annual Raptors free agency primer, which will walk you through the team’s cap situation and what will and won’t be options for them. And over the next few weeks and months, Eric and I will break down these key decisions, potential targets and more. I’ll also be doing a Q&A on Thursday and a mailbag to follow, so keep an eye out for those if you have questions.

TBD — Award winners announced

Last year, this mattered a great deal. Pascal Siakam earning All-NBA Second Team triggered an escalator in his max contract, which was and remains a pretty big deal. There are no similar clauses in any Raptors deals for this season. (Siakam’s escalator applied to his entire contract, it is not year-by-year.) Kyle Lowry was the only other Raptor with relevant incentives in his deal this year, a “likely” bonus that was not achieved since he did not make the All-Star Game.

It would still be nice to see OG Anunoby earn All-Defensive Second Team.

July 22 — Latest possible NBA Finals end date

Fun fact: The Raptors haven’t not won the championship while playing in Toronto since 2018. Masai Ujiri should be playing out a standard pro wrestling trope right now that the Raptors were never defeated for their title. If I’m Ujiri, I’m showing up to the final game of the Finals and claiming “paper champion,” with a challenge to unify the titles next year.

July 23 – Aug. 6 — 2021-22 salary cap and luxury tax set

This is the biggest domino to fall every offseason. Unlike last year, we at least have reasonably reliable projections for the next league year. When the league opted to keep the 2020-21 levels steady with 2019-20 rather than lowering them, they locked in a band of possible increases for future seasons, to spread out the salary cap impact of the pandemic over multiple years. The league and union agreed the salary cap and luxury tax levels will increase by three-to-10 percent each year through the end of the current collective bargaining agreement in 2023-24.

Current projections for 2021-22 using the minimum three-percent increase have the cap and tax at $112.4 million and $136.6 million, respectively. (The high end of that projection range would be $120 million and $145.9 million, but most people I’ve spoken to expect the numbers to come in closer to the lower end this year and next.)

We’ll probably get a more official updated projection from the league before the draft, with the numbers locking in for certain before or during the league’s free-agent moratorium.

June 22 — NBA Draft Lottery

I am not sure if any of you have been aware the last few months but the Toronto Raptors have a pick in the lottery this year. Wild, right?

Jakob Poeltl at No. 9 is the only lottery pick this front office has made while together in Toronto. Every other pick has come outside the lottery, oftentimes being dealt. With the organization’s success finding and developing undervalued talent, it’s fun to think about what they could do with a top prospect.

We’ll find out exactly where they pick on June 22.

The Raptors will have some representative present for good luck, either in-person if the situation allows by then or virtually. (My vote is for Mr. Wayne Embry if travel allows.) There are 1,001 possible combinations of 14 numbered ping-pong balls in a lottery machine, and each team is assigned a certain number of those combinations based on where each team finished in the standings. The lottery machine determines the top four picks — selected out of the 14 non-playoff teams that own lottery combinations — and the rest of the draft order plays out based on end-of-regular season standings.

The Raptors have the following odds of landing at each spot:

• No. 1 pick: 7.5 percent
• No. 2 pick: 7.8 percent
• No. 3 pick: 8.14 percent
• No. 4 pick: 8.52 percent (31.96 percent chance at a top-four pick)
• Nos. 5-6 picks: Not possible
• No. 7 pick: 19.72 percent (average pick of 6.2)
• No. 8 pick: 34.11 percent (highest probability)
• No. 9 pick: 12.88 percent
• No. 10 pick: 1.3 percent
• No. 11 pick: 0.03 percent
• Nos. 12-14 picks: Not possible

(The Raptors can’t move into Nos. 5 or 6 because the lottery draws only the top four picks. No. 8 is the highest probability outcome because it’s the cumulative probability of Nos. 8-14 moving into the top four and bumping the Raptors down one spot.)

July 27 — Rodney Hood decision

Hood has a $10.85 million salary for next season. That amount is fully non-guaranteed, but it locks in early, before the offseason begins. The Raptors will almost surely waive Hood by the July 27 cut-off for that guarantee. That date coming just before the draft erodes some of the non-guaranteed year’s value — the Raptors will have to have a deal in place ahead of the draft and free agency to use Hood’s salary as a trade chip.

July 29 — NBA Draft

There are some key dates within the draft calendar, as well:

• May 30 is the early-entry application deadline
• June 21-27 is the NBA Draft Combine
• July 19 is the withdraw deadline for early-entry applicants

Those are important dates to keep in mind for the player pool and some extra intel on measurables, but the big date is July 29. The Raptors’ front office, many of whom have been working remotely at least part-time, have had far more runway than usual to dig in on prospects. The scouting process is always a year-round affair, but the more hands and eyes on the prep, the better, and the removal of playoff prep and early certainty they’d have a lottery pick should give them a leg up in the process.

As a reminder, the Raptors will have their lottery pick, plus two second-rounders. Those picks will be in the mid-40s, coming from Memphis (via Sacramento for Terence Davis II) and Golden State (via Utah for Matt Thomas). Depending on how the Play-In Tournament goes out West, those picks could fall anywhere from 43 to 48. (You are rooting for the Lakers and Spurs to emerge from the west Play-In to maximize draft position, by the way; the East is inconsequential here.)

Their own second is owed to Detroit via Brooklyn from the Greg Monroe salary dump.

Gary Trent Jr. (Kevin Sabitus / NBAE via Getty Images)

Aug. 1 — Qualifying offers

The Raptors have two potential restricted free agents in Gary Trent Jr. and Jalen Harris. To secure their RFA status and the right to match any offer sheet they sign elsewhere, the Raptors will have to extend them qualifying offers.

As a two-way, Harris’ qualifying offer is part paperwork, part joke. Two-ways receive little in terms of qualifying offer protection. A team would probably have to offer Harris more than the minimum to pry him away, putting the Raptors in a position where if they want to retain Harris, there should be no roadblocks. (A multi-year minimum deal with some up-front guarantee seems realistic, if not another spin on the two-way cycle for further development.)

Trent’s situation is more of a true RFA situation, especially since he locked in a higher qualifying offer earlier this month. As explained in that piece, the Raptors and Trent’s representatives could get creative to minimize Trent’s cap hold and maximize cap space. That would come after they issue him a qualifying offer, though.

The deadline to extend those qualifying offers (or make the players unrestricted free agents) is Aug. 1, the day before free agency begins.

Aug. 2 — Free agency/start of the new league year

You know the deal by now. There is a calendar for NBA free agency, and every year it is obviously ignored with a flurry of deals right at the opening of the free-agent period. This year, the starting line is 6 p.m. ET on Aug. 2.

The free-agent moratorium period extends until Aug. 6 at 12 p.m. ET. That means only certain transactions can take place in that window — RFAs being signed to offer sheets, minimum contracts being signed — and most of the deals you hear reported won’t be made official until Aug. 6 or later. That gives the league time to lock in cap figures and teams time to line up their moves in a particular order that best suits their needs and, in the Raptors case, maximizes cap flexibility.

Lowry, Stanley Johnson and Khem Birch are all unrestricted free agents, in addition to Trent and Harris as RFAs.

Once the free agency window opens, so does trading. (Trading can also take place before or at the draft.) The amount of cash teams can send and receive in trade also refreshes at that point.

Aug. 3 — OG Antidotey

The “poison pill provision” attached to OG Anunoby’s rookie-scale extension is removed on Aug. 3. It is not worth going into specifics other than to say he’s easier to trade, mechanically, beyond that date. And that I wanted to make that poison/antidote joke.

Aug. 4-20 — Guarantees, options and extensions

The Raptors’ cap sheet is loaded with non-guaranteed contracts, and the guarantee triggers for those deals have been staggered across the first two weeks of free agency.

Those guarantee decisions are as follows. (Note: We do not have the exact date-mapping calendar for the offseason ahead yet, hence the lack of specificity in a few cases.)

• Rodney Hood, $10.85 million, July 27
• Aron Baynes, $7.35 million, Aug. 4 or 5
• Paul Watson Jr., $1.7 million, Aug 5 or 6
• DeAndre’ Bembry, $1.98 million, Aug. 6 or 7
• Chris Boucher, $7.02 million, Aug. 8
• Yuta Watanabe, $1.76 million, $375,000 guarantees Aug. 9, the rest if he makes the opening night roster
• Freddie Gillespie, $1.52 million, $50,000 guarantees Aug. 20, the rest if he makes the opening night roster

While some of those seem obvious, each carries a cost and a benefit. Once locked in, those deals eat into cap space. They also become tradeable salaries. The front office in some cases paid extra in the first year of deals to secure this kind of flexibility, for trades and for roster building.

The Raptors will also have to pick up the third-year team option on Malachi Flynn’s rookie deal sometime before the start of the season. That is a mere formality. The $2.15 million option for 2022-23 will be picked up.

There are no players eligible for extensions on the roster this summer.

TBD — The big one

Masai Ujiri is a free agent this summer. He will speak to media Wednesday morning, a session that might not reveal his contract status but should reveal some of the team’s thinking heading into such a big offseason.

We’ll be breaking all of those decisions down in the coming weeks, from Lowry’s future to how to approach the cap situation to how to use the lottery pick and more. Keep an eye out next week for my annual free agency cap primer and later this week for my Q&A session and call for mailbag questions.

(Top photo of Kyle Lowry: Scott Audette / NBAE via Getty Images)