What would a Victor Oladipo trade look like

NBA fans were expecting to have a couple days to catch their breath as they impatiently wait for the NBA Finals to begin on Wednesday, but that break  didn’t last long. As the most dramatic professional sports league, the NBA takes no days off. This afternoon, Jared Weiss of The Athletic reported that Victor Oladipo may be looking to force his way out of Indiana, and while Oladipo has yet to make any public remarks regarding the situation, this news comes as the spilling point of a pot that has been boiling at the brim for a while now.

The 28-year-old has spent his last three seasons playing for the Pacers, where he was able to to thoroughly develop his offensive game, and break out as an All-Star in 2018. During the 2017-2018 campaign, he posted figures of 23.1 points, 5.2 rebounds, and 4.3 assists, while also leading the league in steals per game at 2.4. As an All-NBA’er, and a member of the NBA All-Defensive First Team, Oladipo led his team to The Playoffs as a fifth seed, although they would go on to lose to LeBron James’ Cleveland Cavaliers in the first round.

Though Oladipo’s dominance would continue the following season – even at an elevated level as he had just turned 26 years old – it was prematurely cut short. Oladipo’s season lasted just long enough for him to be named to his second All-Star Team, however on January 23rd, 2019, he suffered a ruptured quad tendon in his right knee against the Toronto Raptors. That injury would not only cost the Pacers their playoff hopes, but it would hold Oladipo out for over 12 months.

When he came back to action on January 29th, 2020, Oladipo wasn’t the same budding young star that he was before. Some rust should be expected after a player hasn’t seen the floor or partaken in ultra competitive basketball for over a year, but Oladipo did not look like his old self. In 19 games this season, Oladipo averaged 14.9 points, 3.9 rebounds, and 2.9 assists per game, while shooting an abysmal 31.7% from deep, and 39.4% from the floor.

Ultimately, Oladipo’s poor play upon his return to action may have been what began to cause some friction in Indiana. With Oladipo set to hit unrestricted free agency in 2021, there are a handful of teams who would happily go into a bidding war for his services, however as most loyal players do, Oladipo first looked into signing an extension in his current market.

According to Ian Begley of SportsNet New York, Oladipo and the Pacers had discussed an extension around the 4 years, $80M mark, but those discussions did not get far, and understandably so. While the injury and his subpar play are legitimate concerns for any team looking to onboard Oladipo, he’s a player whom at his age, given his resume and capabilities, would command close to the maximum contract from a few teams around the league. Such a deal would pen him closer to the 4 year, $160M mark, although that figure is likely to decrease with the NBA working on a new CBA (Collective Bargaining Agreement), due to the economic implications of COVID-19.

To summarize, Oladipo wanted more money than what the Pacers were willing to offer him. It’s not uncharacteristic of an organization that shipped out Paul George in his prime because of George’s frustration with ownership, which stemmed from the fact that they were unwilling to pay the luxury tax to acquire a superstar level player when the opportunity arose.

Oladipo’s failed extension talks may have ultimately played a part in his willingness to sit out from the NBA restart, blaming his decision on the fact that he’d prefer to continue rehabbing his previously injured quad. Oladipo’s reasoning was cheaply bought, as he had already played 13 games prior to the league’s shutdown, and four months of quarantine had gone by where Oladipo had nothing better to do than rest his injured leg. What’s even more convincing of this, is that Oladipo wound up playing six of the Pacers’ eight seeding games in the bubble, plus all four games of The Playoffs, hinting at the fact that he may have been using his ability to sit out the rest of the season as leverage in his contract talks.

Now that the Pacers have been sitting at home for over a month after being eliminated by the Miami Heat, the focus is back on Oladipo, and it’s become clear that his antics weren’t enough to swing the tides. Today’s reports indicate that Indiana’s General Manager, and President, Chad Buchanan, and Kevin Pritchard may have pulled Oladipo’s last straw. Another star player wants to leave Indiana.

While it’s obviously not the optimal case for Pacers fans, their team even without Oladipo is certainly a perennial playoff team, albeit stuck in the upper echelon of mediocrity. They would unequivocally be better with Oladipo on their roster, but that does not mean they should hoard him and his unhappiness for one season, if it means losing him for nothing in free agency next summer. Rather, they could look to trade him now, and get pieces in return to help elevate their contention status.

If Indiana does indeed decide to pull the trigger on the latter course of action, there will be no shortage of suitors around the league, including but not limited to: Boston, Miami, Brooklyn, and Toronto.

With Oladipo’s contract expiring at the end of next season, teams would be able to keep their books clear for the notoriously star-studded 2021 free agency class, and of course, potentially use Oladipo as bait to lure another star next summer, if he were willing to re-sign.

So let’s have some fun: if Masai Ujiri and Bobby Webster were to decide that Oladipo will don the red and black of the Raptors next year, who would they have to send the other way?

With Oladipo set to earn $21M next season, it would be hard to match up the Raptors’ incoming and outgoing salaries given the current roster construction. The only two possible ways to work out a trade would be if Toronto were willing to part with Pascal Siakam or Kyle Lowry, and take back a larger package of Oladipo and one of Doug McDermott, T.J. Warren, or Jeremy Lamb in return, or if Toronto were to call in a massive offer of Norman Powell, OG Anunoby, Patrick McCaw, and some filler salary to get the deal done for Oladipo straight up. Both of these options are highly unlikely to come to fruition.

The third way that the Raptors could creatively land Oladipo would be to sign-and-trade Fred VanVleet to the Pacers. VanVleet would fit perfectly with Indiana’s current core of Malcolm Brogdon, T.J. Warren, and Domantas Sabonis, both age-wise, and style-wise. If need be, the Raptors could easily attach a pick, or a pick swap to sweeten the pot for Buchanan and Pritchard to say yes.

The only complication with a sign-and-trade is that the Raptors and Pacers would have to co-convince Fred VanVleet to go play in Indiana. As an unrestricted free agent himself, VanVleet can choose to play wherever he wants. While the Raptors may have an easier time convincing Freddy to stay North of the border, simply signing him, then subsequently and separately trading him immediately after would be illegal, as a newly-signed player must be on the roster for 90 days before being traded.

While it would be a long and difficult process to get Oladipo to Toronto, and it would mean saying goodbye to our beloved Fred VanVleet, the Raptors would find themselves right at the top of the East again with a big-three of Lowry, Oladipo, and Siakam.

Oladipo would give the Raptors another much-needed shot maker, and someone else to penetrate defenses other than Lowry. He’s a defensive stud, which is an imperative quality to have if you want to see floor time in Toronto, and he’s a great cultural fit. Plus, he’s already buddies with OG Anunoby, as they’re both Indiana Hoosiers alumni.

OG!!!!! BIG TIME!!!!

— Victor Oladipo (@VicOladipo) September 4, 2020

Toronto has already swung for the fences once and capitalized big-time by trading for an undervalued, injured superstar. With Oladipo, they might just strike gold again.