3 Burning questions for Toronto Raptors heading into the offseason

24 years in the making, 2019 was finally the dream season.

Toronto Raptors fans and management can look back at the time when Vince Carter was the team’s superstar.

A Carter jump shot in 2001 that just clanked off the rim in a game 7 second-round series against Philadelphia was the farthest the Raptors had ever advanced in chasing the Larry O’Brien trophy.

It wasn't until 2016 when the Raptors lost to Cleveland in an Eastern Conference Final series would Canada’s team advance past the second round of the NBA playoffs.

June 13th, 2019 was the night that Raptors team president and general manager Masai Ujiri and Bobby Webster planned for and executed which no other Raptor’s management team has been able to do.

However, all good things may come to an end. A risky deal that brought a player in the conversation as potentially the best in this generation, Kawhi Leonard, paid off in spades.

The Raptors were questioned about the wisdom of trading a talent like DeMar DeRozan for a player coming off of an injury that cost him a year in his career and has the option of an opt out of his contract this June.

Ultimately, this experiment paid off, as the Raptors were crowned as the champions, a year after their painful exit at the hands of the Cleveland Cavaliers.

Here is a look at three burning questions for the Toronto Raptors heading into the 2019 offseason:

#3 Will Kawhi Leonard re-sign?

2019 NBA Finals MVP Will he or won't he stay in Toronto?

This is perhaps the single most important question in the history of the Toronto franchise. Will the 2019 Finals MVP, Kawhi Leonard, remain a Toronto Raptors player beyond this season? The answer is unclear and Kawhi Leonard is not a talkative guy.

If money gets this basketball superstar known affectionately as the”Klaw” out of bed in the mornings, the Raptors are likely to have a maximum contract with his name on it totaling $190 million over 5 years or the equivalent over 3 years whichever length deal he prefers.

Leonard has already lost money in whatever he decides to do this offseason when he was traded from San Antonio to Toronto and leaving Toronto so soon after leaving San Antonio further erodes his earning potential (Toronto can offer him more than any other team).

His departure also creates a huge hole to fill. Pascal Siakam has become a rising star, from his drafting at #27, in the 2016 NBA draft.

This year, Siakam's third, saw him become a huge part of the Toronto Raptors. However, its unlikely Siakam is on Kawhi Leonard’s level as early as next season.

Further, with no first-round draft pick at the 2019 NBA Draft thanks to the deal to acquire Leonard, there is no young talent like Siakam coming to the rescue in 2019.

As quickly as the Raptors found the answer to winning it all, that formula may reveal itself to be quick and fleeting. A returning Leonard means the Raptors are likely poised to defend their crown.

#2 What is the Raptors Future at the Center position?

Masai Ujiri gambled big in the 2018 offseason and mdway through last season. The Kawhi Leonard move gave the Raptors a business-like two-way player who also closes out opponents with a killer instinct.

However, adding a Marc Gasol to the chemistry of the team worked but also seems and seemed like a huge mistake.

First, in making the deal, Ujiri moved off the Raptors' roster Jonas Valanciunas.

Valanciunas, at 27 years of age, just entering his prime could be considered the Raptors most consistent playoff performer over the previous five seasons until Kawhi Leonard arrived.

Marc Gasol is a gifted passer as a big man who plays the game with a high IQ. The problem is at 34 going on 35 years of age his effectiveness and efficiency on the floor has been in decline.

It seemed at the time in February that Ujiri made a mistake. Gasol was leaving a Memphis squad that couldn't score much and he was part of the problem. In fact, in 26 games in Toronto with 19 starts, Gasol averaged 9.1ppg and 6.6rpg. These were hardly impressive stats and well below Marc Gasol’s standards.

His playoff numbers were also not great offensively. However, he did a splendid job shutting down Nikola Vucevic of Orlando, Joel Embiid of Philadelphia, and helping to clog the lane against Giannis Antetokounmpo of Milwaukee.

All three of these teams fell victim to the Raptors stifling defense in the playoffs and Gasol was a major contributor even against Golden State in the finals.

While this deal still seems horrible, is that both Gasol and Serge Ibaka play the same position and are getting paid starters money.

Ibaka is owed $23.2 million and Gasol $25.5 million if he chooses to opt into the final year of his contract. It’s obvious he should and will.

It means unless Ujiri makes a deal moving either Gasol or Ibaka and maybe upgrades at the 5 spot with a younger center, through free agency, the Raptors go into 2019-20 with $48 million-plus committed to two centers and one showing signs of aging and decline.

#1 What is Masai Ujiri’s Future?

As both General Manager and President, Masai Ujiri has been the great architect putting together the greatest stretch of basketball by the Toronto Raptors franchise.

Under his guidance and decision making, the Toronto Raptors have won 50 plus games four years in a row.

They have made the Playoffs six straight years, won their division four out of the last 5 years, made the ECF twice, and it all culminated in the team winning the 2019 NBA Finals.

Masai Ujiri was named the NBA’s Executive of the Year in 2013 and is likely to be the recipient for the second time in 2019.

Considering this era of superteam basketball acquiring 3 or more stars to win, Masai Ujiri just led the Toronto Raptors to a title with not one lottery pick or so-called drafted franchise player on his roster.

While Leonard may now be a franchise player, he was not a lottery pick. Ujiri’s roster tweaks and changes have been impressive.

The Raptors have had to beat back suitors for the services of their super executive. In 2017, it was heavily rumored that New York Knicks owner James Dolan had eyes on Masai Ujiri until he decided the move would be too costly to pursue.

The latest talks are that the Washingon Wizards in looking to replace fired executive Ernie Grunfeld are willing to pay Masai Ujiri $10 million and give him a stake in ownership to leave Toronto and guide their troubled franchise.

If Ujiri leaves Toronto for another squad, his departure has ripple effects. Gone would be his masterful roster decisions and talent finding skills (see undrafted Fred Vanvleet or late first round draft pick Pascal Siakam).

Also, with the mystery and angst about Kawhi Leonard’s trust and commitment to Toronto could be weakened if the quiet introspective Leonard has to start a new business relationship with a different Toronto president or management team.

There are so many questions the Raptors will need to answer this offseason. Is Kyle Lowry still the point guard?

Will Siakam become an all-star in 2020 and the future of this team? Is O.G. Anunoby going to be a breakout player in his third year? Will the Raptors be able to defend their crown?

So many questions but time will tell. The NBA Draft is this Thursday and then there is another 10 days or so before players with player options need to declare whether they are opting out of their contracts and becoming free agents. Everyone wants answers now, but they are coming and soon.