Toronto Raptors: Could Kawhi Leonard opt to re-sign for a shorter deal?

The Toronto Raptors want to re-sign Kawhi Leonard this summer. While it is not ideal, signing Leonard to a shorter contract to provide him with more control and flexibility may be the best option.

Life is great. The Toronto Raptors are in the NBA Finals for the first time in franchise history. The series is tied 1-1, but the Raptors had an opportunity to win Game 2. Kawhi Leonard looks like the best basketball player on the planet. The idea of the Toronto Raptors hoisting the Larry O’Brien Trophy actually seems possible.

Despite how good everything is right now, the question in the back of everyone’s mind is, will it be enough to convince Leonard to resign with the Raptors?

When Leonard first asked for a trade last summer, he told the Spurs that he wanted to be traded to Los Angeles, preferably to the Lakers. After Gregg Popovich and R.C. Buford traded him to the Raptors many wondered whether Leonard would even report to training camp. A lot has happened over the past year but not all the worries are gone.

One of the main reasons Leonard’s relationship with the Spurs ended is because the two sides disagreed about the seriousness of Leonard’s right quad injury. The Spurs’ medical staff cleared him to play. Leonard did not feel ready and sought a second opinion outside the team. Then Leonard’s teammates openly questioned Leonard’s decision. At the end of the day, Leonard felt the relationship was beyond repair and requested a trade.

The Raptors have done their best to appease Leonard this season. Michael Grange of Sportsnet recently detailed the relationship between Leonard and Alex McKechnie, the Raptors’ director of sports science. Leonard only appeared in 60 regular season games. He also rested during back-to-backs.

In March, Josh Lewenberg of TSN reported that many Toronto Raptors officials have become increasingly confident in the team’s chances of resigning Leonard. Lewenberg indicated that the Raptors’ free agency pitch would focus on familiarity, a commitment to maintaining Leonard’s health and the shared goal of pursuing a championship.

The Raptors know Leonard will have other suitors when free agency opens; one team in particular, the Los Angeles Clippers. The Clippers have made their intentions known all season. Doc Rivers was recently fined $50,000 for his comments about Leonard.

Even though other teams will be in pursuit of Leonard, new details have emerged about the possibility of Leonard staying in Toronto. David Thorpe recently reported that those at TrueHoop had “heard from plugged-in sources associated with players and the league – but not the team – that Kawhi would return to Toronto, at least on a short-term deal.”

A lot has been written about the Raptors’ ability to offer Leonard a fifth year and almost $50 million more than any other team. This was the first report suggesting that Leonard might consider signing a shorter contract.  By doing so, Leonard would maintain greater control over his future.  After all, Leonard has already shown that money isn’t everything.

Last summer, Leonard became eligible to sign a super max contract extension. The Spurs had the ability to offer him a five-year, $221 million contract. Leonard turned it down and requested a trade.

Now the Raptors can offer Leonard a five-year, $190 million contract. But Leonard might be prepared to sign elsewhere or for less if it means playing on a team that has the ability to be an annual contender. Leonard isn’t concerned with the notoriety that typically comes with being one of the best players in the NBA. He just wants to win.

In advance of Game 1 of the NBA Finals, Leonard was asked about being less famous than players like LeBron James and Steph Curry. Leonard’s response was that isn’t why he plays the game. Leonard has shown that his priorities are having a long, healthy career and competing for championships.

Leonard isn’t the only one. Today’s NBA players want to have control over their careers. LeBron James ushered in a new era of basketball when he took his talents to South Beach. Kevin Durant followed suit when he joined the Golden State Warriors. In recent years both James and Durant have opted to sign shorter contracts in order to maintain flexibility and control. Leonard may be the next superstar to follow the trend.

There are a number of reasons that Leonard might consider signing a one-plus-one or a two-plus-one (a two or three-year contract, with the final year being a player option).

The Toronto Raptors as currently constructed are a legitimate title contender. However, Kyle Lowry and Marc Gasol are 33 and 34 years old, respectively. Danny Green is set to be a free agent this summer. Serge Ibaka, Fred VanVleet and Pascal Siakam will all be free agents in 2020. It is unclear how long the Raptors’ title window will stay open.

The summer of 2020 has always been targeted by Masai Ujiri and Bobby Webster as an opportunity to rebuild or retool. The Raptors only have two players under contract beyond next season (Norman Powell and OG Anunoby). The salary cap is also projected to increase to $116 million for the 2020-21 Season. Powell and Anunoby are set to make a combined $14.7 million leaving the Raptors will significant cap space to pursue free agents.

If Leonard were to resign, his salary for that season would be $35.3 million. The Raptors would only have about $51 million in committed salaries once you factor in their 2020 first round picked (I am using the no. 28th overall pick at $1,136,800).

Another complicating factor is a potential contract extension for Pascal Siakam. He is eligible to sign an extension before the start of next season. However, the Raptors should strongly consider holding off until summer 2020.

Siakam has emerged as a borderline All-Star. He is the front-runner for the Most Improved Player Award and is in line to receive a large raise. Siakam currently earns $1.5 million. The first year salary on his next contract could be as high as $29 million (25 percent of the salary cap).

Signing Siakam to an extension now would cut into the Raptors potential cap space next summer. Siakam’s cap hold will be much lower than whatever his salary is under a new contract. Since Siakam makes less than the league average salary, his cap hold will be 300 percent of his current year’s salary or $7,055,516.

By waiting the Raptors could have more than $50 million in cap space. This would give the front office a number of avenues to rebuild around a core of Leonard, Siakam, Anunoby, and Powell. Leonard would also have the flexibility to leave after one season if he did not like the direction of the team.

The other benefit to Leonard by signing a shorter contract is a financial one. Since Leonard has between seven and nine years of experience, he is eligible to sign a contract starting at up to 30 percent of the salary cap. Two years from now, Leonard will have 10 years of experience. That means he will be eligible to sign a new contract starting at 35 percent of the salary cap.

Assuming the salary cap increases by $2 million for the 2021-22 Season and goes up to $118 million, Leonard could sign a contract starting at $41.3 million. A 30-year-old Leonard would be eligible to sign a five-year contract worth $242 million. While Leonard has shown that money isn’t everything, if the Raptors continue to be a contender, there is no reason not to enjoy the spoils that go along with it.

Kawhi Leonard is a superstar. He has taken the Raptors further than they have ever gone before. While the front office would probably like to lock Leonard down for as long as possible, they will also take what they can get. A new three-year contract could provide both sides with just enough that everyone walks away happy, but still hungry enough to continue striving for more.