Lowry Lost, Oladipo Found: One Potential Offseason Strategy If the Raptors’ GOAT Walks Away

By Pete Baxter

Kyle Lowry was heavily shopped around the league prior to the NBA trade deadline. Masai Ujiri, Bobby Webster and company in the Raptors’ front office were never able to find the ideal haul to ship their star point guard out of town. The 76ers, Lakers, Clippers and Heat were among the team’s rumored to have made overtures for the 35-year-old vet.

With the Raptors’ brutal, roller coaster season having to come a close, Kyle Lowry enters the market as an unrestricted free agent. Many assume the Raptors and Lowry’s camp may already have a sign-and-trade scenario in mind. This would explain the Raptors reluctance to move their star at the deadline despite having little-to-no hope for a playoff run.

However, the ball is in Kyle Lowry’s court. If he does not see a strategic advantage to agreeing to a sign-and-trade deal, and believes he has an ideal offer waiting for him on the open market, the Raptors could very well lose the man widely considered the greatest Raptor of all-time for nothing.

So, what would come next?

The Passing of the Torch

Should Lowry move on from Toronto, the Fred VanVleet era officially begins. VanVleet is a 27-year-old natural point guard who had started at the shooting guard position next to Lowry for the past several seasons.

VanVleet is a similar player to Lowry. He is an undersized guard who makes up for his lack of size with tenacious defense, a nose for the basket and a great shooting touch. He is a natural leader and would slide naturally into the starting point guard position. VanVleet put up borderline All-Star numbers last season of 19.6 points, 4.2 boards and 6.3 assists per game while shooting just under 37% from three.

Malachi Flynn, in his second season, would become the primary back up to VanVleet. Flynn saw his playing time increase as his rookie season went on. He showed flashes of brilliance and earned 14 starts in relief of injured starters while averaging 7.5 points, 2.9 assists and 2.5 rebounds per game.

This duo is more than prepared for the increased responsibility.

Filling the Gap

With Lowry moving on and Fred VanVleet moving to the primary point guard role, we are left with a gap in the backcourt to be filled. Fortunately, the $30 million in salary freed up by Lowry’s absence gives the Raptors a great deal of flexibility.

To handle the duties at shooting guard, there is one familiar and one not-so-familiar face that could prove to be perfect fits.

First, the Raptors must retain Gary Trent Jr. Brought over in a deadline trade for Norman Powell, Trent looked outstanding in the 17 games he played for the Raptors. He put up 16.2 points, 3.6 rebounds, 1.3 assists and 1.1 steals while shooting just under 36% from three as a Raptor. He even dropped a career-high 44 points on 19 shots against the Cleveland Cavaliers.

Trent is a restricted free agent, and at just 22 years old it is imperative that the Raptors match any reasonable offers and keep him in house. For a deal in the area of four years, $18 million per season, the Raptors should have their shooting guard of the future locked up (or at least, a perennial Sixth Man of the Year candidate).

Keeping Trent is a no-brainer. He fits perfectly into the young core of VanVleet, OG Anunoby and Pascal Siakam. However, if the Raptors want to make a real splash on the free agent market and replace Kyle Lowry’s veteran toughness and leadership, there is one more big name they should strongly consider.

Enter Victor Oladipo

Oladipo is a two-time All-Star who has proven himself capable of leading a team on a playoff run during his time in Indiana. He has career averages of 17.5 points, 4.6 rebounds, 4.0 assists, and 1.6 steals per game. He is an excellent two-way player.

Unfortunately, his career over the past three seasons has been derailed by injuries. Since the 2018/19 season, Oladipo has played in totals of just 36, 19, and 33 games by season. However, even in his limited play last season between Houston, Indiana, and Miami, he still averaged just under 20 points per game along with 5.7 rebounds and 1.7 steals.

He can clearly still be a force, but can he stay healthy? The good news for Toronto, is this should be an affordable gamble with a huge potential payout. Oladipo will most likely need to sign a “prove it” contract this year, a short-term, affordable deal to show he can stay healthy and get back to 100% to earn another big contract next year.

The Raptors could likely acquire Oladipo’s services for a deal in the one year, $16 million range. Oladipo is expected to be available from his current knee injury sometime early next season (tentatively in November per a recent report from Adrian Wojnarowski of ESPN).

The Raptors would be able to take their time bringing Oladipo back from injury as their starting shooting guard position would already be in good hands with Trent Jr. By the time next year’s All-Star break comes around, the Raptors could be featuring a formidable starting back court of Fred VanVleet and Victor Oladipo with Gary Trent Jr. providing an enormous offensive spark off the bench.

Oladipo would bring toughness, leadership and experience to this team to fill the void left by Lowry and would give the Raptors a considerably more balanced lineup than the dual point guard approach of the past few seasons.

A Look at the Lineup

With Oladipo and Trent Jr. locked down, the last order of business for Toronto would be to nail down their center position. Fortunately, they have that answer in-house already as well.

Khem Birch was a rare bright spot in an otherwise disastrous second half of the 2020/21 season. After being cut by the Orlando Magic midseason, the Raptors took a flier on the 28-year-old big man and he made the most of the opportunity. Birch went on to average 11.9 points, 7.6 boards and 1.2 blocks per game in 19 games (17 starts) for the Raptors after taking over for the struggling Aron Baynes.

Birch, a native Canadian, should be relatively affordable to keep, perhaps on a two-year deal worth around $15 million. Paired with this year’s other break out player Chris Boucher, the Raptors would have their center position well-staffed moving forward.

At this point, to ensure I free up some additional cap space to make these moves, it would be wise to send Aron Baynes to the first team willing to send over a second-round pick. Veteran Rodney Hood, another deadline addition with his non-guaranteed $10.8 million contract, is also being shipped out of town.

So, let’s take a look at where this leaves the Raptors’ lineup prior to draft night 2021:

PG: Fred VanVleet, Malachi Flynn

SG: Victor Oladipo, Gary Trent Jr.

SF: OG Anunoby, Deandre Bembry, Paul Watson

PF: Pascal Siakam, Yuta Watanabe, Freddie Gillespie

C: Khem Birch, Chris Boucher

Within this group there are as many of five players with current All-Star potential. They maintain a similar mix of veteran, championship swagger and developmental talent. This team, if allowed to return to their home base in Canada next season, could easily top 50 wins and find themselves back in the thick of Eastern Conference contention.

As discussed in previous articles, the Raptors would be well-suited to utilize this year’s first-round selection to beef up their point guard depth. That said, with their poor record this year, they have potential to beat the odds and secure a true lottery pick. If so, a potential star like Evan Mobley could fall into their lap. This could secure their center position through the draft as well. We will dig deeper into potential draft strategies as we approach the July 29 draft date.

This is arguable the most pivotal offseason the Raptors have had since they began a near-decade of winning basketball back in 2013. From front office (Masai Ujiri himself and his lack of contract extension) throughout the lineup there are difficult questions to be answered.

The faces of the Toronto Raptors could look quite different in 2021/22. More to come from (hopefully) Toronto.

Published by Pete of the North

Avid sports fan and obsessed statistician. Binge drinker turned writer. Toronto Raptors fan since the O.G. Zan Tabak. Based out of Albany, NY. Cheers!

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