Two months ago, Kyle Lowry was cradling the Larry O’Brien Trophy, hugging his kids and celebrating an NBA Championship with his teammates. From 2012 to the present, the Toronto Raptors point guard was both the emotional igniter of the team and the target of immense scrutiny. The countless times coming up short were put to rest this past June, when Lowry played a critical role in providing the Toronto Raptors their first NBA title in franchise history.

Once the euphoria subsided, the team underwent significant changes. Most notably the departure of Kawhi Leonard and Danny Green, who are headed to the marquee Los Angeles franchises.

But what remains constant for the Raptors is the presence of veteran experience and leadership, with Kyle Lowry as the focal point. Couple this with the return of Marc Gasol, Serge Ibaka and Fred VanVleet, along with the positive progression of last year’s Most Improved Player Pascal Siakam, and you have a Raptors team permeated with championship mettle.

As Lowry enters the final year of his three-year, $100 million contract, the battle-tested point guard hopes that his irreplaceable contributions to the team will matter during negotiations.

“I want to be there,” Lowry said in a recent interview. “I would love to do an extension, but we’ll see what happens. We’ll have the discussion when the time is right.”

In addition to the $33.2 million average annual salary, Lowry will receive $1.2 million in bonuses for the 2019-20 season. Entering his 15th season in the NBA, the Raptors starting point man is coming off his fifth All-Star appearance, averaging 14.2 points, 4.8 rebounds and 8.7 assists. Lowry’s performance in the postseason, most notably his 26 points in the championship-clinching Game 6 against the Golden State Warriors, quashed the preconceived notion of the point guard not raising his level for big games.

Player Age 2019-20 2020-21 Kyle Lowry 33 $33,296,296 Marc Gasol 34 $25,595,700 Serge Ibaka 29 $23,271,604 Norman Powell 26 $10,116,576 $10,865,952 Fred VanVleet 25 $9,000,000 Patrick McCaw 23 $4,000,000 $4,000,000 Stanley Johnson 23 $3,623,000 $3,801,000 Pascal Siakam 25 $2,351,839 OG Anunoby 22 $2,281,800 $3,872,215 Cameron Payne 25 $1,737,145 $1,977,011 Rondae Hollis-Jefferson 24 $1,737,145 Malcolm Miller 26 $1,588,231 Chris Boucher 26 $1,588,231 Dewan Hernandez 22 $898,310 $1,517,981 Sagaba Konate 22 Oshae Brissett 21 Devin Robinson 24 Justin Hamilton 29 $1,000,000 Team Totals $122,085,877 $26,034,159

(table by: Basketball Reference)

Cap space will not be a concern for the Raptors when Lowry becomes an unrestricted free agent after next season. The team’s payroll will decrease from $122.1 million this season to $26 million for 2020-21. With the contracts of Lowry, Ibaka, VanVleet, Gasol and Siakam expiring, it will increase the cap room for the Raptors to $146.8 million for the 2020-21 season.

Toronto Raptors Salary Cap Totals 2020-21 Active Roster Cap $ 32,162,367 Cap Holds $ 114,677,717 Total Cap Allocations $ 146,840,084

(table by: Spotrac)

Where the hesitation will lie for Raptors President Masai Ujiri to resign Lowry is the career stage he is in. Currently 33 years old, the Philadelphia native is entering the twilight of his career. Where “Father-Time” can activate at any moment, causing a sharp decline in production on both ends of the court. Injuries have also been a point of concern with Lowry, missing games due to ailments ranging from thigh contusions to back pain. In July, the Raptors point guard had surgery on his injured thumb from the Playoffs, demonstrating an unfortunate pattern of physical issues that will worsen with age.

In addition to getting older, Lowry will also have to contend with the rise in performance of fellow Raptors teammate Fred VanVleet. VanVleet, only 25 years old and entering the prime of his career, became a Raptors hero when he generated 22 points (12 in the fourth quarter) in Game 6 of the NBA Finals. The point guard’s defense of Steph Curry yielded the two-time NBA MVP shooting 1-for-6 from the field in 33 possessions. If VanVleet continues to make an effective impact on the court, he will be next in line to assume the mantle for starting point guard. Making it more unlikely for the Raptors to resign the ageing Kyle Lowry.

In July, Lowry made the savvy move to sign onto Priority Sports Agency, the same group representing NBA stars Bradley Beal and Gordon Hayward. The five-time All-Star is preparing for an intense free agency which will include contract negotiations with Raptors management. There are three options that the Raptors front office can choose from regarding Lowry’s future:

Sign a short-term deal for lesser money.

Sign a short-term deal for more money.

Trade Kyle Lowry for future assets.

Given his career accomplishments, it is not surprising that Lowry will be asking for more than his $33.2 million per year in annual salary. The Raptors would be very content to keep their franchise star at a cheaper price tag, similarly to how the New Orleans Pelicans are keeping guard Jrue Holiday on a $26.4 million annual salary. If the Raptors are interested in signing younger players to build for the future, the organization may not have enough money to satisfy Lowry’s asking price.

The best option is to trade Kyle Lowry for future assets. With the asking price too high for the Raptors to keep Lowry, the sensible move would be to trade Lowry in order to acquire future pieces to build around. Teams like the Utah Jazz, which would benefit from guard depth and possess a plethora of draft picks, could be a potential landing spot for Lowry, who is eager to contend for a championship later in his career.

Unfortunately for Raptors fans, parting ways with Lowry will bring back sour memories of previous stars leaving this team. Masai has shown that he is unafraid of trading away fan favourites, evidenced when he sent Demar DeRozan to the San Antonio Spurs for Kawhi Leonard. If the Raptors are struggling when the trade deadline approaches, the organization would rather get future assets for Lowry, rather than let him sign elsewhere for nothing in return.

In his tenure with the Raptors, Lowry has become the best point guard in franchise history. There will be a time for contract talks with the Raptors. But in the meantime, Lowry’s sole focus is utilizing his high basketball intelligence and competitive spirit to keep the Raptors relevant in their title defense.

“We’re still going to be able to run it back. We’re the champions and we’re trying to defend our title. I’m confident with our team,” Lowry said.

Savour the time that Lowry has left with the Raptors. His time with Toronto is waning.