Raptors Notes: Lillard, Siakam, Anunoby, Barnes, Holiday

The Raptors were willing to part with a slew of draft assets to acquire Damian Lillard, according to Michael Grange of Sportsnet.ca, but a Western Conference source tells him they were hoping to reach a deal with the Trail Blazers that didn’t include Pascal Siakam, OG Anunoby or Scottie Barnes.

Grange hears that Toronto’s offer included up to three future first-round picks, two pick swaps and rookie forward Gradey Dick. Team officials believed they could become title contenders by adding Lillard to their existing talent, but not by having him replace one of their key components.

The fact that the Raptors were involved in discussions for Lillard shows that the front office isn’t content with the team in its current form, observes Eric Koreen of The Athletic. Big decisions are coming up soon that will affect the organization’s future, and team officials will have to determine whether they’re planning to contend or rebuild.

Siakam and Gary Trent Jr. both have expiring contracts and are currently eligible for extensions. Another potential free agent next summer is Anunoby, who has a $19.9MM player option for 2024/25 that he’s expected to decline. Koreen notes that means the window is closing on a potential win-now move if the Raptors don’t do something by February’s trade deadline.

There’s more from Toronto:

  • The Raptors aren’t likely to pursue Jrue Holiday, who is reportedly back on the market after being sent to Portland in the Lillard deal, Grange states in the same piece. Toronto wanted Lillard to provide more spacing for Barnes and Siakam, and Holiday isn’t on the same level as an outside shooter.
  • The Raptors haven’t held any extension talks with Siakam, Grange adds. Siakam will become eligible for a super-max deal if he remains in Toronto and makes an All-NBA team in 2024.
  • In a separate story, Koreen looks at questions for every player on the Raptors’ roster, including the need for a new lead guard after the loss of Fred VanVleet in free agency. He notes that Dennis Schröder normally excels at getting into the paint, but he may find that more difficult as Toronto doesn’t have enough outside shooting to provide driving lanes.
  • Toronto pulled off a G League trade this week, with the Raptors 905 acquiring the rights to Denzel Valentine from the Maine Celtics in exchange for Kylor Kelley, tweets Blake Murphy of SportsNet.

Inside The Damian Lillard Trade

Damian Lillard had become more involved with the Trail Blazers over the past two weeks and was preparing to attend training camp with the team if he didn’t get the trade he requested, according to Shams Charania and Sam Amick of The Athletic.

After nearly three months of waiting, that deal came together on Wednesday, sending Lillard to the Bucks in a three-way trade that also involved the Suns. Lillard hadn’t been reconciling with Portland, the authors add, but he was working out at the team facility and interacting with coaches and teammates to show that he was willing to remain patient as the Blazers’ front office tried to find a trade.

Lillard’s agent, Aaron Goodwin, informed general manager Joe Cronin early in September that Lillard was open to participating in camp if a deal didn’t happen before then, sources tell Charania and Amick, and Lillard told team officials that he would be “fully present” for the start of the season while trade talks continued.

However, the authors’ sources say Cronin didn’t want the distraction of having Lillard on the roster when camp began and preferred to get a deal out of the way before Monday’s media day. He viewed the Lillard situation as “a cloud over the organization” and wanted the team to be able to focus on the season ahead without having to worry about Lillard’s future.

Charania and Amick provide more inside information about Wednesday’s blockbuster:

  • When Lillard made his trade request on July 1, he told team officials he only wanted to go to Miami and was expecting to be rewarded for his years of loyalty to the organization. Charania and Amick confirm the Blazers and Heat talked several times in July, but the negotiations never became “substantive,” according to the authors’ sources. Portland asked for Jimmy Butler or Bam Adebayo in its first call, and Miami eventually decided that Cronin wasn’t serious about working out a deal with them.
  • Sources tell Charania and Amick that in July and August, the Heat were willing to part with three first-round picks, multiple second-rounders and pick swaps, along with Nikola Jovic in a proposal that would have sent Tyler Herro to a third team. However, the Blazers weren’t interested and the relationship between Portland and Miami started to become contentious. It’s worth noting that Miami didn’t technically have three tradable first-round picks available due to an obligation to the Thunder and the Stepien rule.
  • Cronin began serious trade discussions around the league on September 18 and found interest from the Bucks, Celtics, Pelicans, Raptors, Timberwolves and Bulls. All those teams wanted to acquire Lillard, but they were concerned about Portland’s asking price and whether they would have enough talent left on their roster after a deal to compete for a title.
  • Tensions reached a point where Cronin stopped responding to Goodwin in mid-September, sources tell Charania and Amick, and Goodwin began to explore other options that might appeal to Lillard. He was willing to consider the Bucks and Nets, and Goodwin communicated his interest to both those teams. The Raptors also had serious interest, but Lillard’s reluctance to play there was an obstacle until the end, the authors note.
  • The authors’ sources say the Suns started discussing the framework of a Deandre AytonJusuf Nurkic trade in mid-July, but the Blazers wanted to make sure they could avoid the luxury tax when Lillard was eventually dealt. Phoenix would likely have been part of any deal with the Bucks, Nets or Heat, Charania and Amick add.

New York Notes: Simmons, Nets, Knicks, Fournier

Count veteran guard Spencer Dinwiddie among those who are bullish on Ben Simmons‘ chances of enjoying a big comeback season in 2023/24. As NetsDaily relays, Dinwiddie heaped plenty of praise on his Nets teammate during a recent appearance on Patrick Beverley’s podcast.

“Ben at his best form is a far more athletic Draymond Green with less three-point shooting,” Dinwiddie said. “… When you talk about the defensive IQ, reading passing lanes, quarterbacking a defense, able to guard one through five. He’s one of the only people in the league who can do that, and then obviously he’s getting out on that break.

“… When Ben’s at his best, he’s getting off the rim, he’s being a monster in transition, he’s making plays for others,” Dinwiddie continued. “We hope that there’s enough shooting out there with Mikal (Bridges)Cam Johnson obviously is elite, he’s always shooting 45 (percent) from three … Catch and shoot-wise I’ve been a good three-point shooter in my career. We hope to space the floor for him. He gets out in transition and makes plays. And obviously you’ve got Nic (Claxton) playing above the rim.”

Simmons’ comments in August about how he was eager to “come back and dominate people” after recovering from his back issues were met by many fans with skepticism and some derision. However, people who have spent time around the former No. 1 overall pick this offseason believes those quotes are “based on substance,” according to Ian Begley of SNY.tv, who has heard from those sources that Simmons looks like he’s primed for a bounce-back year.

Here’s more on the NBA’s two New York teams:

  • Defensive rebounding and outside shooting look like two potential Nets weaknesses based on their current roster, according to Brian Lewis of The New York Post, who suggests that how Brooklyn overcomes – or addresses – its shortcomings in both areas could go a long way toward determining what sort of season the team has.
  • Michael Pina of The Ringer lays out the case for why the Knicks are in position to target an impact player and why New York may be a more appealing landing spot for stars than it has been for years. In a related story, Adam Zagoria of NJ.com argues that the Knicks should go all-in for trade candidate Jrue Holiday.
  • After stating in July that he’d be “very surprised” if he opens the season with the Knicks, Evan Fournier sounds more resigned to that scenario, according to Stefan Bondy of The New York Daily News (subscription required), who passes along highlights from Fournier’s appearance earlier this month on French radio station RTL. The veteran wing acknowledged that he doesn’t have much control over the situation, but simply wants the opportunity to play again. “I love living (in New York), I love the franchise, I love playing at Madison (Square Garden), I love the guys on the team,” Fournier said. “So I just want to play, that’s all. It’s true that finding another club, changing franchises, if that’s what you have to do to play again, that’s what I would like to do.”
  • In his latest mailbag, Fred Katz of The Athletic fields questions on Fournier’s status, the Knicks‘ rotation, and Julius Randle‘s recent agency change. While Katz doesn’t believe Randle’s decision to leave CAA means he wants to leave the Knicks, he refers to the move as “significant,” noting that the timing (following the first season of a four-year contract) is unusual.

Spurs Sign RaiQuan Gray

The Spurs have filled their 21-man offseason roster by signing free agent forward/center RaiQuan Gray to a training camp contract, per RealGM’s transaction log.

The 59th overall pick in the 2021 draft out of Florida State, Gray spent his first professional season in the G League with the Long Island Nets. He signed a training camp contract with Brooklyn in the fall of 2022 but didn’t make the regular season roster and was cut before opening night, ultimately spending a second season in Long Island before being promoted to a two-way deal during the final week of the 2022/23 season in April.

After an underwhelming rookie season at the G League level, Gray emerged as a full-time starter in ’22/23, averaging 15.4 PPG, 7.6 RPG, and 2.6 APG with a .578/.382/.629 shooting line in 18 games (30.6 MPG). However, he was waived by Brooklyn this summer, making him an unrestricted free agent.

The Austin Spurs – San Antonio’s G League affiliate – acquired Gray’s returning rights from Long Island in an NBAGL trade last month. That move, along with Gray’s new training camp contract, signals that San Antonio will likely waive the big man ahead of the regular season and have him report to Austin.

Assuming Gray’s new deal includes Exhibit 10 language, he’ll be in line to earn a bonus worth up to $75K if he spends at least 60 days with the Spurs’ G League team.

Scotto’s Latest: Grant, Nurkic, Payne, Nowell

Following the trade of Damian Lillard, the Trail Blazers are expected to immediately begin listening to trade inquires on newly acquired guard Jrue Holiday. However, he may not be the only notable veteran on the roster who is on the trade block in advance of this February’s deadline.

Rival league executives who spoke to Michael Scotto of HoopsHype anticipate that Jerami Grant will also be available via trade in the not-too-distant future. Due to the terms of the new contract he signed with Portland in July, Grant won’t become trade-eligible until January 15, so if he’s going to be moved this season, it would have to happen between Jan. 15 and Feb. 8, this year’s trade deadline.

Grant’s five-year, $160MM contract would represent a significant cap commitment for any team interested in acquiring him, but his two-way contributions would make him an on-court fit for virtually any contender.

“Grant could be the missing piece for a contending team the way Denver got Bruce Brown and Aaron Gordon,” one NBA scout told Scotto. “Maybe a team like Miami could take a swing if they’re still a player away.”

Here are a few more highlights from Scotto’s latest rumor round-up:

  • Moving Jusuf Nurkic, who has three years and $54MM+ left on his contract, was a goal for the Trail Blazers in any Lillard trade, but there’s a belief that a fresh start in Phoenix, where he’ll anchor Frank Vogel‘s defensive scheme for the Suns, could help rejuvenate him, writes Scotto. “Before Nurkic got injured, he was a good defensive center and was Portland’s second-best player ahead of CJ McCollum for a short time,” a scout told HoopsHype. “I think it might be asking too much of him to return to his pre-injury form, but he can help them if he’s properly motivated and healthy with dribble handoffs and as a positional defender.”
  • League sources tell Scotto that the Bucks and Heat are among the teams to watch for free agent point guard Cameron Payne. Milwaukee, with no clear backup point guard, was previously identified as a clear fit for Payne after the Lillard trade opened up a roster spot. Miami also doesn’t have much depth at the point after losing Gabe Vincent this summer.
  • Free agent wing Jaylen Nowell recently worked out for the Kings, sources tell Scotto. Nowell is one of the most noteworthy members of this year’s free agent class who remains unsigned, while Sacramento has just 14 players on guaranteed contracts, leaving one open spot on the team’s projected regular season roster.

Bucks Acquire Damian Lillard In Three-Team Trade

9:37pm: The trade is now official, the Bucks announced in a press release.

Damian Lillard is an elite player in our league and someone we’ve long been fans of,” said general manager Jon Horst. “These opportunities are rare and hard to measure and execute. We are incredibly grateful for this opportunity for our community and team, and beyond excited to welcome Damian and his family to the Milwaukee Bucks. His character, competitiveness, talent and experience complement our group and gives us the best chance to win at the very highest level as we create new memories together.”

These are the hardest, most human moments of this business. Jrue was unmatched in his commitment to the Bucks and the Greater Milwaukee community,” Horst said of Holiday. “He’s truly a champion on and off the court, and we are all thankful for what he and his family have given to our team and city. He and his wife Lauren were steadfast in their efforts to make a positive difference in the lives of so many people. Their leadership and dedication to the community has left an indelible mark and inspired the Bucks organization for years to come.”


1:22pm: The Bucks have reached an agreement to trade for star Trail Blazers guard Damian Lillard in a blockbuster three-team deal that also includes the Suns, reports Adrian Wojnarowski of ESPN (Twitter links).

According to Wojnarowski, Portland will acquire guard Jrue Holiday and an unprotected 2029 first-round pick from the Bucks, along with the right to swap first-round picks with Milwaukee in 2028 and 2030. The Blazers will also get center Deandre Ayton and rookie forward Toumani Camara from the Suns in the deal.

In exchange for Ayton and Camara, Phoenix will receive center Jusuf Nurkic, forward Nassir Little, and guard Keon Johnson from Portland, as well as wing Grayson Allen from Milwaukee, per Woj.

The massive deal is the culmination of a saga that lasted nearly three months after Lillard requested a trade out of Portland in early July. The seven-time All-Star had spent his entire 11-year NBA career with the Trail Blazers but felt that the team was no longer moving toward championship contention following consecutive lottery seasons and sought a change of scenery.

Miami was Lillard’s landing spot of choice, but reports throughout the process indicated that there was little communication between the Heat and Trail Blazers. In recent days, with the Blazers believed to be working to make a deal before the start of training camp, other Eastern Conference suitors like the Raptors and Bucks were increasingly connected to the 33-year-old.

Milwaukee ultimately emerged as the surprise winner of the Lillard sweepstakes, beating a handful of conference rivals to the punch and strengthening a core that also includes two-time MVP Giannis Antetokounmpo and standout starters Khris Middleton and Brook Lopez, both of whom signed new free agent contracts with the club this offseason.

While there have been questions about whether Lillard would be happy to report to any team besides the Heat, both he and Antetokounmpo have expressed a desire to play with one another in the past, as Chris Haynes of Bleacher Report and Alex Kennedy of BasketballNews.com point out (all Twitter links). And the Bucks should put Lillard in a better position to win a championship than he ever had with the Blazers.

Meanwhile, Antetokounmpo may not be any more inclined to sign a long-term extension with the Bucks following the acquisition of Lillard than he was earlier in the offseason, given that he would benefit financially from waiting another year. However, in dealing for another star like Lillard, the Bucks’ front office proved it heard Giannis’ call for the organization to be as committed to contending for titles as he is.

The Blazers, who patiently scoured the market for most of the offseason in the wake of Lillard’s trade request, will come away from the deal with a pair of intriguing new players in Ayton and Holiday, though the big man is more likely to remain in Portland than the veteran guard.

According to Wojnarowski (Twitter link), the Blazers – who are focused on developing a young backcourt that features Shaedon Sharpe, Anfernee Simons, and this year’s No. 3 overall pick Scoot Henderson – remain engaged in trade talks involving Holiday and could flip him to a contender for additional assets.

Holiday, who can become a free agent next summer if he turns down his 2024/25 player option, recently spoke about his desire to sign a contract extension with the Bucks, but now appears destined for a new long-term NBA home. Holiday will become extension-eligible in February, though as Bobby Marks of ESPN notes (via Twitter), he won’t be able to sign a contract that exceeds the extend-and-trade limits (two new years, 5% raises) until six months after being dealt.

On the other hand, it sounds like Ayton will be a keeper for the Blazers, who have had interest in the former No. 1 overall pick in the past and were linked to him again within the last week. The 25-year-old had an up-and-down five-year stint in Phoenix that included some tension with former Suns coach Monty Williams, but he has averaged a double-double for five straight seasons, including 18.0 points and 10.0 rebounds in 30.4 minutes per game across 67 contests last season.

As for the Suns, they recognized that a player such as Ayton, who liked to have the ball in his hands, might not be an ideal fit alongside their new big three of Kevin Durant, Devin Booker, and Bradley Beal, and turned the young center and his $32.5MM cap hit into a series of role players on smaller contracts, including another big man in Nurkic.

Acquiring Nurkic, Little, Allen, and Johnson will make the Suns deeper and will give them more flexibility in future trades, given that their nearly all of their non-stars had been on minimum-salary contracts. However, the move creates a bit of a roster crunch in Phoenix. The club will now have 15 players on guaranteed contracts, plus Jordan Goodwin and Ish Wainright on partially guaranteed or non-guaranteed deals. At least two of those 17 players will have to be traded or cut before the regular season tips off.

While the Suns will increase their roster count as a result of this trade, the Bucks and Trail Blazers are both sending out more players than they’re taking back. That’s especially notable for Milwaukee, which had been carrying 15 players on guaranteed salaries prior to agreeing to acquire Lillard. The Bucks now project to have an open spot on their 15-man regular season roster, which could be used to add a backup point guard.

From a cap perspective, the Bucks will take on the biggest long-term deal in the three-team trade — Lillard is under contract for four more seasons and will earn a projected $216MM during that time, while Holiday ($36.86MM) and Allen ($8.93MM) could both reach free agency next summer.

The Blazers will owe Ayton approximately $102MM over the next three years before he becomes eligible for free agency. Camara is under contract for four years, but it’s a minimum-salary deal and only the first season is guaranteed.

The Suns will take on Nurkic’s three-year contract worth $54.38MM and Little’s four-year contract worth $28MM in addition to Allen’s expiring deal. Johnson is owed a guaranteed $2.81MM salary in 2023/24 and has a $4.47MM team option that the Suns must pick up or decline by October 31, if he’s still on the roster at that point.

Celtics Sign Jordan Schakel To Non-Guaranteed Camp Deal

The Celtics have signed free agent guard/forward Jordan Schakel, according to Keith Smith of Spotrac (Twitter link). It will be a non-guaranteed training camp deal, Smith adds, likely featuring Exhibit 10 language.

A 6’6″ wing, Schakel went undrafted out of San Diego State in 2021. He caught on with the Wizards for his rookie season, signing an Exhibit 10 contract before being waived and spending the bulk of 2021/22 with their NBA G League affiliate, the Capital City Go-Go.

Schakel, who signed a 10-day hardship deal with Washington during the COVID-19 outbreak a couple years ago, inked a two-way contract with the Wizards prior to last season, but was released last November. Overall, he has played in six NBA games for 36 total minutes, all with the Wizards.

While he hasn’t played much at the NBA level, he was a G League regular the past two seasons. In 2022/23, he spent the fall Showcase Cup with the Go-Go, averaging 14.4 PPG, 3.6 RPG and 2.1 APG on .451/.360/.919 shooting over 17 games (31.3 MPG).

However, after spending six regular season games with the Go-Go, he finished last season with Golden State’s affiliate, the Santa Cruz Warriors. Overall, he averaged 10.9 PPG, 4.3 RPG and 1.5 APG on .452/.399/.862 shooting in 33 combined games with the two clubs (25.5 MPG).

It’s worth noting that since Schakel’s returning player rights are held by the Warriors, the Celtics will have to acquire his G League rights if the plan is for him to spend the upcoming season with their NBAGL affiliate in Maine, which seems highly likely. If he’s waived before the season starts, he could earn a bonus worth $75K — in addition to his G League salary — if he spends at least 60 days with Maine.

After signing Schakel, the Celtics now have 20 players on their roster ahead of training camp, one shy of the offseason limit.

Fischer’s Latest: Payne, Bucks, Allen, Suns, Ayton

Trading Jrue Holiday and Grayson Allen in the Damian Lillard blockbuster created a roster opening for the Bucks, who still need a backup point guard. Free agent Cameron Payne is worth keeping an eye on for that spot, league sources tell Jake Fischer of Yahoo Sports.

As Fischer writes, the Bucks considered several trade packages last season that would have sent Allen to the Suns when they were pursuing Jae Crowder. Milwaukee eventually landed Crowder at the February deadline without involving Allen, but he’ll end up in Phoenix as part of this deal, which shows the club’s interest in the sharpshooting guard was indeed legitimate.

The Suns added two extra players in the three-team deal, sending Deandre Ayton and Toumani Camara to Portland and receiving Allen, Jusuf Nurkic, Nassir Little, Keon Johnson. They now have 17 players on standard contracts, with Johnson ($2.8MM guaranteed) and Ish Wainright ($1.9MM non-guaranteed) the top early candidates to be waived ahead of the 2023/24 season, sources tell Fischer.

Jordan Goodwin‘s deal for ’23/24 is only partially guaranteed, but Fischer hears Phoenix decided to move Camara instead because Goodwin is friends with Bradley Beal and is the only point guard on the roster.

As for Ayton, Suns players and front office members alike were “eager for a change of direction,” according to Fischer, which is why the club decided to trade the former No. 1 overall pick. For his part, Ayton is glad to have a “fresh start” in Portland, sources tell Fischer.

Timberwolves Sign Tyrese Martin

9:00pm: The signing is official, per RealGM’s transactions log.


1:10pm: The Timberwolves have reached an agreement on a one-year contract with free agent wing Tyrese Martin, reports Shams Charania of The Athletic (Twitter link). According to Charania, Martin will get the opportunity to compete in camp for a spot on Minnesota’s regular season roster.

The 51st overall pick in the 2022 draft, Martin was waived in July after appearing in just 16 games for the Hawks last season as a rookie. He scored 21 points and grabbed 12 rebounds in his 66 total minutes at the NBA level.

Martin saw more frequent playing time for the College Park Skyhawks in the G League, averaging 18.0 PPG, 9.2 RPG, and 1.9 APG on .503/.366/.805 shooting in 23 regular season contests (33.9 MPG) for Atlanta’s G League affiliate. However, the Hawks opted against locking in the second year of his minimum-salary contract, cutting him before his guarantee date.

The details of Martin’s deal with the Wolves are unclear, but I expect it’ll be a non-guaranteed minimum-salary contract, possibly with an Exhibit 10 clause.

Minnesota currently has 14 players on guaranteed standard contracts and three on two-way deals. However, at least one of those two-way spots is believed to be up for grabs, with Matt Ryan expected to compete to keep his roster spot. If Martin gets an Exhibit 10 contract, it could be converted into a two-way deal before the regular season begins.

If Ryan and the Wolves’ other two-way players hang onto their spots and the team decides to carry a 15th man into the regular season, Martin would be competing against camp invitees such as Vit Krejci, Trevor Keels, and Daishen Nix to fill that final roster opening.

Jrue Holiday Rumors: Sixers, Harden, Clippers, Heat, Celtics

As first reported by Kyle Neubeck of PHLY Sports, the Sixers have interest in trading for veteran guard Jrue Holiday, who is being sent to Portland as part of the Damian Lillard blockbuster. Keith Pompey of The Philadelphia Inquirer confirms Neubeck’s report, and says James Harden — who hopes to land with the Clippers — would be involved in a possible deal.

Holiday spent his first four NBA seasons with the Sixers, who selected him 17th overall back in 2009. According to Pompey’s sources, Philadelphia tried to trade for Holiday multiple times during his seven-year stint with New Orleans from 2013-20.

Moving Harden before Monday’s Media Day and next week’s training camp would avoid a messy situation, and the team has said it wants an All-Star caliber player or draft assets in return for the former MVP. As a five-time All-Defensive member and a two-time All-Star, Holiday fits that bill, Pompey notes.

A three-team deal that sends Harden to the Clippers, Holiday to the Sixers, and a first-round pick from each club to the Trail Blazers seems like it could be a good move for all parties, according to Jake Fischer of Yahoo Sports, who reports that L.A. has thus far only been willing to give up one first-rounder for Harden. Still, as Fischer observes, maybe the Clippers will just end up going after Holiday instead.

The Heat are another Eastern Conference contender who have long valued Holiday, sources tell Fischer. League executives were speculating about Holiday being sent to Miami in the aftermath of the deal, Fischer adds, though it’s worth pointing out that Portland and Miami haven’t had much dialogue this offseason, despite Lillard hoping to land with the Heat.

The Celtics are expected to consider a pursuit of Holiday as well, reports Adam Himmselsbach of The Boston Globe (via Twitter). That’s an interesting, though not surprising rumor — the team has been trying to mend fences with Malcolm Brogdon, who was nearly sent to the Clippers this offseason. Brogdon ($22.5MM) would basically have to be involved in any package for Holiday ($36.86MM) for salary-matching purposes.

If the prolonged Lillard saga is any indication, Portland’s front office could be patient in looking for the best possible return for Holiday, Fischer notes.