Lowry, Ujiri and roster upgrades: Here's what to expect from Raptors in free agency

It’s finally here! Free agency officially starts at 6 p.m. ET on Monday. We use the word officially in air quotes because everyone knows the behind-the-scenes maneuvering between teams, players and agents has already started. The Raptors have a couple of huge questions they need answered before potentially venturing into the open market to restock their roster, so here’s a quick primer on what to expect this week:

Where is Kyle Lowry headed in free agency?

This is not only the biggest domino for the Raptors, it is arguably the biggest domino of the entire free agency:

Several teams, including the New Orleans Pelicans and Dallas Mavericks, have cleared enough cap space to make a substantial offer to Kyle Lowry, who is reportedly looking for a new contract in the range of $90 million over three years.

The Miami Heat also made a few moves on Sunday, declining a $15 million team option on Andre Iguodala and picking up a $19.4 million option on point guard Goran Dragic. As ESPN’s Adrian Wojnarowski reported on Sunday, Miami is considered the front-runner to acquire Lowry although getting him the most money will require a sign-and-trade with the Raptors.

The Heat can offer the Raptors a trade package built around Dragic—who would most likely be re-routed to another team or accept a buyout from Toronto—and Precious Achiuwa, Miami’s first-round pick in the 2020 draft. The Raptors are not obligated to engage in a sign-and-trade, but doing so would help facilitate moving their beloved starting point guard to the destination he prefers while ensuring he’s getting paid the maximum amount possible. On the other hand, Toronto does have some (albeit minimal) leverage in negotiations with Miami as the Pelicans and Mavericks can sign Lowry outright with their cap space.

The details of how Lowry ends up in Miami will need to be sorted out, but at the moment, it appears wherever he ends up, the greatest Raptor of all time will be moving on this summer.

Will restricted free agent Gary Trent Jr. return to the Raptors?

The second most pressing question of the summer for the Raptors is restricted free agent Gary Trent Jr., who Toronto acquired at the trade deadline from Portland in exchange for Norman Powell.

The entire fanbase is currently hanging on to every single photo from Scottie Barnes’ tour through Toronto over the weekend (he is possibly getting a Raptors face tattoo as we speak), but Trent Jr., who won’t turn 23 until next January, also projects to be part of the team’s core group moving forward.

The latest reporting via Bleacher Report’s Jake Fischer indicates the Raptors will get a deal done with Trent Jr. in the range of $50 million over three years. Barring a surprise, Trent Jr. will be playing in Toronto next season.

When will Masai Ujiri sign a new contract with the Raptors?

We still don’t have an official announcement from the Raptors on Masai Ujiri’s contract status. Because of the moving NBA calendar due to the pandemic, Ujiri’s contract is believed to have been extended past July 1 to accommodate for last week’s NBA Draft, where the Raptors president of basketball operations was front and centre in the war room as the team’s draft selections were announced.

It is still possible Ujiri could walk away at this point—anything is possible until the two sides put pen to paper. But it would be strange for him to leave after being so involved in drafting Barnes and presumably with free agency in the days ahead. The expectation is still for Ujiri to return, although no one has a clear idea on what the hold-up is.

Who will the Raptors target in free agency and trade?

The Raptors have reportedly been pretty active in trade talks with other teams. They were recently linked to the Philadelphia 76ers as an interested suitor in point guard Ben Simmons. However, the Sixers reportedly asked for Kyle Lowry, OG Anunoby, Fred VanVleet and the No. 4 pick in return. There also continues to be rumblings Pascal Siakam is available for the right package.

Until he traded for both Kawhi Leonard and Marc Gasol, the Raptors under Ujiri had been pretty patient when it comes to blockbuster trades. They’ll surely canvas the rest of the league for opportunities to improve the roster, but the (expected) departure of Lowry and the addition of Barnes at the draft means it’s still more likely than not Toronto won’t make a trade this summer that significantly alters the roster.

This brings us to free agency. The Raptors could have a pretty significant amount of cap space to work with, assuming Lowry walks away in free agency without the team having to take back an equivalent amount of salary in a sign-and-trade. There are also several other scenarios where the team could open up some cap space to pursue free agents.

The Raptors have been linked to Lonzo Ball, but the restricted free agent is expected to either return to New Orleans or sign an offer sheet in the four-year, $80-million range with Chicago. There are plenty of point guards available in the open market, including Chris Paul and Mike Conley—although both are expected to sign new deals to remain in Phoenix and Utah respectively. The next tier includes Dennis Schroder, Patty Mills and Spencer Dinwiddie, who are either not a great fit with the team’s timeline, will be asking for too much money, or both.

Toronto could pass on adding a lead ball-handler on the open market altogether. They have VanVleet, Malachi Flynn and even Barnes, who has plenty of experience playing point guard. Dalano Banton and David Johnson, the team’s recent second-round picks, are likely headed for the G-League, but that’s two more point guards in the team’s developmental system.

The Raptors are more likely to add a big man to the roster in free agency. The two most intriguing names are John Collins and Jarrett Allen, who are both 23 and would fit the team’s timeline and potentially be a core piece moving forward. The problem is both are coveted around the league and are restricted free agents, which means Atlanta and Cleveland can (and probably will) match any offer sheet they receive in the open market.

It leaves the Raptors with other options like New York Knicks centre Nerlens Noel and Sacramento’s Richaun Holmes. Noel is probably the more affordable option, while Holmes will not be cheap but has a higher upside. Toronto will also need to decide whether to bring back free agent Khem Birch on a new contract. The Montreal native was a welcomed addition to the team at the end of last season and is expected to be back in the fold, although the Raptors probably would prefer to add a starting centre in free agency and have Birch serve as the first big off the bench.

There are plenty of possibilities for Toronto as the free agency period starts. The most likely scenario appears to be a Lowry sign-and-trade with Miami, a new contract for Trent Jr., and then a few fringe additions in the open market. Ujiri and the Raptors have surprised us before, though, so prepare for everything, just in case.

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