Toronto Raptors: The case for and against signing OG Anunoby to a contract extension this offseason

Entering the league, OG Anunoby was often compared to Kawhi Leonard. Anunoby has taken Leonard’s place in the starting lineup and now the Toronto Raptors must decide how to deal with Anunoby’s future.

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NEW YORK, NEW YORK - JANUARY 04: OG Anunoby #3 of the Toronto Raptors in action against the Brooklyn Nets at Barclays Center on January 04, 2020 in New York City. Toronto Raptors defeated the Brooklyn Nets 121-102. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Mike Stobe/Getty Images)

The NBA world is still trying to figure out if and when it is going to reopen for the season. During this downtime, it makes sense to take a look at some of the most important questions facing the Toronto Raptors this offseason.

A number of key players are set to be free agents. This includes Fred VanVleet, Marc Gasol, Serge Ibaka, Rondae Hollis-Jefferson, and Chris Boucher. The Raptors would like to keep VanVleet. But as arguably the top point guard on the market this summer, he will have a number of suitors once free agency starts.

In addition to decisions on free agents, the Toronto Raptors must decide whether or not to sign OG Anunoby to a rookie-scale contract extension.

Under the NBA’s collective bargaining agreement, players entering their fourth season under a rookie contract are eligible to sign a rookie-scale extension. This rule only applies to former first-round picks. Teams have until the day before the season starts to agree to terms on a new contract.

If the incumbent team and their former first-round pick cannot agree to terms on a new deal, then that player can become a restricted free agent. Assuming the incumbent team extends a qualifying offer then they have the right to match any contract offers that the player receives following his rookie contract.

In general, the maximum amount that a team can offer is 25 percent of the salary cap. This figure can be increased if the player has been named to an All NBA Team, MVP or Defensive Player of the Year.

Last summer, Pascal Siakam, Ben Simmons and Jamal Murray all signed new maximum contracts starting at 25 percent of the salary cap. These extensions will start at the beginning of the 2020-21 season.

In addition to those three, Jaylen Brown, Buddy Hield, Dejounte Murray, Caris LeVert, Taurean Prince and Domantas Sabonis all agreed to new contracts with their respective teams. As a result, a significant number of potential restricted free agents were taken off the market and further weakened the 2020 free agent class.

It is unusual that such a high number of former first-round picks would sign contract extensions. With nearly one-third of those eligible signings new deals it was almost double the previous season.

In 2018, only five players received rookie-scale extensions: Karl-Anthony Towns, Devin Booker, Myles Turner, Larry Nance Jr. and Justise Winslow. Similarly, the year before only four players signed extensions: Joel Embiid, Andrew Wiggins, Gary Harris and T.J. Warren.

Entering the offseason, there are at least two players guaranteed to sign a rookie-scale extension: Jayson Tatum and Donovan Mitchell. A few others are likely to get new deals in De’Aaron Fox, Bam Adebayo and Jonathan Isaac. Beyond that it is a lot of question marks.

For the Raptors, they have to decide how much they are prepared to commit to Anunoby at this stage of his career. There is no doubt that the Raptors want to lock Anunoby up long term. However, there are a number of factors that must be considered before the two sides agree to terms on a new contract.

The chief concern, as is generally the case in a salary cap driven league, is money. The Raptors are restricted in terms of how much they can spend in order to build a championship caliber team. Committing too much money to Anunoby could impact their ability to make other moves down the road.

As such, let’s examine the case for and against signing Anunoby to a contract extension this summer.

The case for signing OG to a new deal

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OG Anunoby - Toronto Raptors (Photo by Vaughn Ridley/Getty Images)

Anunoby was originally projected to be a lottery pick. He underwent season ending knee surgery during his sophomore year at Indiana. Anunoby saw his draft stock plummet due to concerns about when he would be able to return to the court. The Raptors selected him at no. 23 overall. Meanwhile, Anunoby’s rehabilitation went better than anticipated and he was able to suit up on opening night.

Anunoby started 62 games as a rookie. Expectations were high entering year two. A lot has been written about Siakam’s breakout campaign last season and his Most Improved Player award. However, before the season started Anunoby was viewed as the most promising young prospect on the roster.

It is still shocking that Masai Ujiri and Bobby Webster were able to make a trade for Kawhi Leonard without having to give up either Anunoby or Siakam.

Unfortunately, Anunoby struggled to stay on the court during the Raptors’ championship run. He suffered a concussion early in the season. Anunoby’s father passed away. Finally, Anunoby underwent an emergency appendectomy and missed the playoffs.

With Leonard gone, Anunoby was able to step back into the starting lineup. He didn’t have the breakout season that many fans were hoping for. But Anunoby has shown improvement in all aspects of his game.

This season Anunoby is averaging 10.7 points, 5.4 rebounds, 1.6 assists, and 1.4 steals per game. He is playing a career-high 30 minutes per night. Anunoby is also knocking down 38 percent of his triples.

Those numbers don’t tell the whole story. At just 22 years old, Anunoby has shown flashes of becoming an All NBA level defender. He was starting to put it all together when the season was suspended. During the final seven games between late February and early March, Anunoby averaged 14.7 points, 5.9 rebounds and 3.1 steals per game.

Anunoby has tremendous size for his position. He measured 6-foot-7.75 (in shoes) at the draft combine. Anunoby also has a massive 7-foot-2.25 wingspan. Anunoby’s size and length, plus his chiseled 232 pound frame, allows him to guard multiple positions.

The Toronto Raptors have the second-best defensive rating in the NBA trailing only the Milwaukee Bucks. Anunoby is routinely tasked with guarding the opposing team’s top perimeter player. He has to regularly match up with power wings like Leonard, LeBron James, Paul George, and Jimmy Butler.

Anunoby is able to hold his own against the league’s best. He is also great at getting into passing lanes and causing deflections. Anunoby recorded three or more steals 11 times this season. He had a career-high seven steals in a loss to the Denver Nuggets on March 1.

A frontcourt pairing of Anunoby and Siakam should give the Raptors two of the best defensive forwards in the entire NBA. They are also both just entering their prime. Siakam is locked up for the next four seasons. It makes sense that the Raptors would want to do the same with Anunoby. The price just has to be right.

A few years ago, the Washington Wizards rewarded Otto Porter Jr. with a four-year, $106 million contract extension. This was after he averaged 13.4 points, 6.4 rebounds and 1.5 steals per game. At just 23 years old, Porter looked like the perfect complement to John Wall and Bradley Beal.

Porter is a strong two-way player. He is one of the best three-point shooters in the NBA. But paying more than $25 million annually for a player who has problems creating offense for himself and others is a lot. This is why the Wizards traded Porter to the Bulls before last season’s trade deadline.

If the Raptors are able to lock up Anunoby to a new contract starting at around $15 million annually, it might make sense to do so. Looking at similar contracts around the league, that’s the price to keep a versatile wing player.

Two years ago, Winslow signed a three-year, $39 million contract with the Heat. Prince signed a two-year, $29 million contract with the Nets. Kelly Oubre Jr. also agreed to a two-year, $30 million contract with the Phoenix Suns. The promise that Anunoby has shown should put him in a similar category. Those contracts would be a reasonable baseline for negotiations.

However, the problem with signing Anunoby to a new deal now is it could impact what the Raptors are able to do long-term.

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The case against signing OG to a new deal

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NEW ORLEANS, LOUISIANA - FEBRUARY 04: Giannis Antetokounmpo #34 of the Milwaukee Bucks reacts against the New Orleans Pelicans during a game at the Smoothie King Center on February 04, 2020 in New Orleans, Louisiana. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this Photograph, user is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Jonathan Bachman/Getty Images)

It isn’t a secret that the Raptors are positioning themselves to make a run at Giannis Antetokounmpo in the summer of 2021. But the Raptors aren’t alone in the desire to add The Greek Freak.

The Bucks are on record stating that they intend to offer Giannis the summer max when he becomes eligible in the offseason. Even if Giannis does want to stay in Milwaukee, he doesn’t need to sign now.  If the Bucks fail to win the title this year, Giannis can decide to wait and sign the exact same contract next summer.

A lot of players are eager to sign a long term deal for financial security. But the same rules don’t apply for superstars.

This past summer, the Brooklyn Nets signed Kevin Durant to a four-year, $164 million contract even though he was set to miss the entire season with a torn Achilles. When healthy, Durant is one of the three or four best players on the entire planets. As such, paying Durant even though he wouldn’t step on the court for 12 months was still a prudent investment. The same would be true for Giannis.

Assuming the season resumes at some point in time, Giannis appears to be a lock to get his second consecutive MVP trophy. Giannis is only 25 years old and just entering his prime. He is fully capable of playing all five positions. Even if Giannis were to suffer an injury next season, there would still be any number of teams lining up to offer him a max contract.

In addition to the Raptors and Bucks, the Knicks, Heat, and Warriors all have their sights set on Giannis. His free agency will be the biggest storyline since “The Decision” in 2010. As a result, the Raptors have to be careful in terms of managing their payroll.

Currently, the only players with guaranteed contracts for the 2021-22 season are Siakam and Norman Powell (player option). Dewan Hernandez and Matt Thomas also have small unguaranteed deals. The Raptors will have their 2020 and 2021 first-round picks. Plus the team will look to sign VanVleet to a new contract this summer.

The salary cap is projected to increase to $125 million in 2021. However, the NBA could lose around $1 billion due to the coronavirus. The salary cap is directly related to revenue. Marc Berman of the New York Post reported the NBA is preparing for the cap to drop next season. That would likely impact projections for the 2021-22 season as well.

This brings us back to Anunoby. He will be a restricted free agent in the summer of 2021. The way the CBA works is if the Raptors don’t sign Anunoby to a new deal before free agency, he is assigned a cap hold. This is a placeholder amount representing his new contract, which counts against the salary cap.

For Anunoby, his cap hold will be $11.6 million (300% of his previous year’s salary). If the Raptors believe they can sign Anuonby to a new deal at $11.6 million or less then it makes sense to lock him up this offseason. However, if the Raptors believe Anunoby’s new contract will start at a figure higher than $11.6 million, it makes sense to wait.

The Toronto Raptors have the ability to go over the cap to re-sign Anunoby. The Raptors can keep Anunoby’s hold, use their cap space to sign Giannis, and then re-sign Anunoby at a larger figure.

If we are assuming that Anunoby’s next contract will start at around $15 million annually, then the Raptors might want to wait.

The only risk there is Anunoby could get offended that the Raptors made him wait and refuse to sign a multiyear deal. Anunoby could instead opt to sign a one-year qualifying offer and become an unrestricted free agent the following summer.

A maximum contract for Giannis would start at $37.5 million. If VanVleet’s new contract were around $20 million annually and Powell exercises his player option, the Toronto Raptors would have just enough room to offer Giannis a max deal. Signing Anunoby to a new contract first at a number higher than his cap hold would mean the Raptors would have to shed salary elsewhere.

Next: It is time for Gasol to come off the bench

As long as Giannis doesn’t sign a new contract before the start of next season Ujiri and his staff will have to think long and hard before committing resources elsewhere. Anunoby has shown the ability to be a legitimate two-way player. I’m sure the hope is that Anunoby will be in a Toronto Raptors’ uniform for years to come. But it’s not every day that the reigning MVP becomes available.