Raptors Cage

Toronto Raptors Trade Deadline Primer

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What Went Wrong This Season?

When Masai Ujiri and Bobby Webster made the decision to trade for Kawhi Leonard in 2018, they were knowingly sacrificing the short term future of the Toronto Raptors for a chance to win it all. At 2019’s trade deadline, having already put all of their chips in the centre of the table, they decided to dive even further into contention and drive further along the road that they were traveling on by dealing for Marc Gasol. By this point, they had consolidated a plethora of Toronto’s assets, and cut deep into their roster’s depth. The likes of Jonas Valanciunas, Delon Wright, C.J. Miles, DeMar DeRozan, Jakob Poeltl, a first-round pick that eventually became Keldon Johnson, and a 2024 second-round pick were sent out the door, in favour of bringing a championship to Toronto, and nobody ever looked back until now.

Debating whether the process was worth it is asinine. Any arguments that one might try to make against the risks that the Raptors took are quickly shut down by the banner that now hangs in Scotiabank Arena. But, it all came at a cost – one which wasn’t evident in 2019 because of the superteam that the Raptors fielded night in and night out – but one which is taking its toll this season.

The now 17-26 Raptors have lost nine games straight, which is good for the longest active losing streak in the NBA, after allowing the Houston Rockets to snap their 20-game skid at Amalie Arena last night. While the team is not nearly as horrible as their record suggests, still equipped with several fringe All-Star players, they have unequivocally had their wheels knocked off by a multitude of off-court factors.

Five thoughts recap: Houston Rockets 117, Toronto Raptors 99 - Raptors HQ
(Bob Levey/Getty Images)

To state the obvious, the Raptors are the only team who have been forced to play every single one of their games on the road. That’s accompanied by the added stress of players, coaches, and staff having to figure out where their kids should go to school, when they will travel back home to see their family, and where they’ll be sleeping at night when the team is staying in Tampa. It’s likely what caused the team to get off to an ugly 2-8 start to the season.

After personal matters seemed to be dealt with however, the Raptors started to roll, just as everyone expected they would. Between January 14th and February 21st, the team won fourteen of their games and lost seven, which included triumphant victories over the Philadelphia 76ers, the Brooklyn Nets, and the Milwaukee Bucks.

Then, the inevitable was realized.

When we’re all so focused on making up fake trades, watching the standings, or enjoying some good ol’ basketball, it becomes easy to forget that we’re living through a global pandemic. Finally, after dodging the virus for so long, COVID-19 introduced itself to the Raptors. Pascal Siakam, Fred VanVleet, OG Anunoby, Patrick McCaw, and Malachi Flynn were all forced to miss time after being infected with, or being exposed to the plague.

It was in those couple of weeks where all of the Raptors weaknesses were exposed, and they fell off the rails. The team’s role players failed to compensate for the stars who were sidelined, and with Kyle Lowry and Norman Powell being called on to shoulder the squad’s entire offensive workload, the team sputtered and dropped five games straight. When VanVleet was finally allowed to return to action, he called out the young guys, saying that it was a “missed opportunity for a lot of guys on our roster.”

Then, against the Detroit Pistons, who happen to hold the worst record in the Eastern Conference, Siakam and VanVleet were finally cleared to return to the starting lineup. In what should have been an easy win, Toronto lost in heartbreaking fashion.

Fast forward another couple of days and the Raptors found themselves facing off against the league’s very best: the Utah Jazz. In what would have been an improbable win, Toronto was up five points with just over a minute of clock left to kill in the fourth quarter. Unfortunately, shot selection down the stretch coupled with Siakam’s fourth in-and-out buzzer beater of the season killed them, and anyone who had bet money on them in that contest. Two more utterly disappointing losses later, and here we are: two days away from the trade deadline.

Why The Raptors Should Sell

The Raptors are typically rather quiet at this time of the year. There are always trade rumours flying around on Twitter, Reddit, RealGM, and wherever else people get their fake news nowadays, however almost always, deadline day ends with Bobby or Masai speaking to the media about how they scoured the market, had a couple of ongoing conversations, but didn’t stumble upon any deals which they were in love with.

This year might just be different. The Raptors should be – or rather, have to be – sellers. With 29 games to go, they sit four games outside of a playoff spot. Undoubtedly, if they kept this current group together, they could sneak in as a five or six seed and make some noise in the first… maybe second round. But, this isn’t 2014 anymore. The goal should be to win another championship, as opposed to continually getting some more playoff experience for the young guys on second tier team. Especially with COVID-19 inhibiting the Raptors ownership from being able to profit off ticket sales this year, there are no financial repercussions for missing the playoffs either. If there’s a golden time to start retooling and tinkering with the roster, it’s now. Getting beat in the second round – regardless of how proud you may feel for taking two games off Milwaukee, Brooklyn, or Philadelphia, simply does more harm to this franchise than it does good.

The reason why? There is a cost attached to that. Kyle Lowry and Norman Powell are both in the last year of their contracts, and they will both be unrestricted free agents this summer. By opting not to trade them before Thursday March 25th at 3:00pm EST, you risk letting both of them walk for nothing.

Kyle Lowry

Let’s start by dissecting Lowry’s situation. Kyle has been with the Raptors for nine years, although it feels like he’s never played anywhere else. All six of his All-Star appearances have been as a Raptor, and the time that he’s spent North of the border has encapsulated the most successful moments of his career. He’s the greatest Raptor of all-time, and it’s possible that nobody will ever take that away from him.

The only issue now is that he is 35-years-old. He doesn’t fit the timeline of the rest of the Raptors core whom they have locked up on long-term contracts, and with only a couple years of star-player-level basketball left in him, Kyle’s probably looking to compete for another championship as opposed to teaching young guys how to contend long after he’s gone. Pair this along with the fact that Lowry sold his house in Toronto a couple of weeks ago below asking price, and one would have a pretty good indication that he’s begun looking to take his talents elsewhere.

As Imman from Dishes and Dimes put it, it’s rare that a team and their star player are both ready to move on from each other at the same time. When the Raptors dealt DeMar, he wasn’t ready to move on. When the Rockets dealt James Harden, the team wasn’t ready to move on. Right now, the Raptors are looking to get younger, and Kyle is looking to win elsewhere. It’s like they’re having a mutually exclusive break-up which only happens in movies.

According to ESPN’s Brian Windhorst, “Kyle’s free agency is happening right now. The expectation is that Kyle Lowry is going to have a new contract by the end of this week. It’s either going to be to stay in Toronto… it’s going to be Miami, or it’s going to be Philadelphia.” Obviously, Lowry wouldn’t actually be able to put pen to paper this week, however it’s likely that each of these front offices is having discussions with the Philadelphia native to gauge where he wants to go in the offseason. If he’s planning on leaving for Miami or Philadelphia, then Toronto will trade him there pre-emptively to gather assets in return. If he says he wants to stay, then it’s likely he won’t be dealt at all.

The latest from Sportsnet’s Michael Grange is that Toronto and Miami are progressing in discussions to send Lowry to South Beach, however the Heat are reluctant to give up Tyler Herro in any deal, and prefer to surrender the 26-year-old Duncan Robinson instead. It’s likely that either player would be heading to Toronto in addition to Goran Dragic, Kelly Olynyk, and either Precious Achiuwa, or a first-round pick, if a deal is made.

Should a deal be found with Philadelphia instead, there are numerous different permutations of packages that Ujiri and Webster could try to pry from the 76ers. Likely the counterpart of any trade that lands Lowry back in his hometown would be Danny Green, simply because getting off from his $15M expiring salary would allow the Sixers to make space for their incoming point guard. In addition to Green, the Raptors could look to snag Tyrese Maxey, Mattisse Thybulle, Isaiah Joe, Paul Reed, or any of the Sixers first-round picks between 2021 and 2024.

What’s even more interesting with the 76ers trade scenario is that according to Windhorst, an unnamed third team would supposedly be interested in joining that transaction, and taking Danny Green off the Raptors hands in exchange for assets. Presumably that team might be Dallas, since they were interested in Green as a free agent in 2019. If that’s the case, Toronto may be able to flip Danny Green for some combination of Dwight Powell, Tyler Bey, Tyrell Terry, or Josh Green.

While saying goodbye to Lowry would certainly be emotional, Kyle made it clear a couple of weeks ago that he wants to retire as a Raptor, “even if it’s on a one day contract.” It sucks that Kyle may not have played his last game as a Raptor in Scotiabank Arena in front of the fans that adore him, but his jersey retirement ceremony should be equally as electric.

Norman Powell

Onto the latter half of the likely-to-be-dealt Raptors this week: Norman Powell. Unlike Lowry, Powell has spent his entire career in a Raptors uniform. After being picked with the 46th overall pick in the 2015 NBA Draft, Norm has had a turbulent path to stardom. He’s constantly dealt with injuries, which have set him back several times, and had robbed him of any consistent role on the team during his first four years in the league. Last season after finally breaking out and winning an Eastern Conference Player of the Week award however, things started to look up for him. His $11M contract – which seemed like a monstrosity on the books before his stellar shooting became a factor – now seems like a discount. In last year’s playoff run, it wouldn’t even be an exaggeration to say that Norm was probably the third best player on the team.

With Powell’s performance having only elevated this year to the point where he is among the most efficient all-around scorers in the entire NBA, he is due to command a large contract in the summer – one which the Raptors might not be looking to pay him, because of his shortcomings defensively, and his age. Rather than letting him walk for nothing, similarly to the Lowry situation, it’s in the Raptors best interest to deal him prior to Thursday’s deadline and get some young assets in return.

NBA: Toronto Raptors Trade Deadline Primer
(Trevor Ruszkowski/USA TODAY Sports)

According to ESPN’s Zach Lowe, there are over ten teams who have called the Raptors inquiring about Powell’s availability. Pretty much any team in the league could match his contract salary-wise, and make a good use of his services too. He has championship experience and is a great veteran leader who can help a young team build for the future; he’s an elite scorer who could help a middle-of-the-pack team make a strong playoff push; and his ability to hit big shots in the clutch or bolster a bench unit’s offense could be invaluable to a contender.

The latest from Michael Grange is that it’s “close to inevitable” Powell gets traded before Thursday evening. In this situation, because there will be such a wide range of offers on the table and so many teams in the mix, it’s hard to gauge what type of return the Raptors might be able to get from trading Norm, however it’s safe to assume that the Raptors would want a solid young player plus possibly some draft compensation in consideration.

Among some names to look out for in a potential Powell trade are Lonzo Ball, Mitchell Robinson, Spencer Dinwiddie, and even Myles Turner.

There will certainly be a lot to look forward to before Thursday’s trade deadline, and possibly an equal amount to stress about. Just remember though – nothing is over until it’s over, especially in the NBA.


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