The final Toronto Raptors game played at Scotiabank Arena in 2023-24 had very little in common with the first. Expectations had been erased, nearly the entire roster turned over, the present and future direction of the franchise shifted, and the quality of play had, to be kind, decreased.
There was one stark similarity, though. In both games — a pre-season contest against Australian side Cairns and a drubbing at the hands of the playoff-bound Indiana Pacers — Javon Freeman-Liberty stood out in a field of developing players hoping to make their case as a part of the team’s long-term plan.
Back in October, Freeman-Liberty was on a two-way contract. Signed after a standout Summer League performance with the Chicago Bulls, Freeman-Liberty was fairly secure in his roster spot but hoping to impress early, possibly earning early-season bench minutes at the NBA level or, likelier, just starting his Raptors 905 season on the right foot. He took full advantage of his minutes, and while 15 points in 14 minutes doesn’t mean a ton against a non-NBA team, Freeman-Liberty’s knack for the paint as a cutter, offensive rebounder and second-side attacker was obvious.
Fast-forward to Tuesday’s home finale, and Freeman-Liberty was starting in an actual NBA regular season game, something even his most optimistic believers would have called a stretch goal for the season. Freeman-Liberty once again took advantage, attacking a sleepy Pacers defence for 14 points in the first quarter and a career-high 20 points overall. He knocked down a pair of threes — something the team believes he’s very capable of beyond his 27-per-cent mark in the NBA and 35.8-per-cent mark in the G League this season — and got into the paint with both feet, a skill that remains in high demand on the current roster. He added eight rebounds, too, something that points to a hustle level that’s similarly been in short supply at times this year.
Freeman-Liberty’s season had some detours (a persistent ankle injury robbed him of NBA chances earlier in the year when the Raptors desperately needed another guard) but there’s no way you could be lower on him now than you were in October. He was a monster scorer for Raptors 905, nearly doubled his assist rate while being asked to handle more traditional point guard duties, and has been very well-liked as a culture piece from Day 1. While he’s a bit undersized as a two-guard and not really a point guard, there’s enough there at both ends of the floor that the Raptors converted him to a standard contract that includes a $100,000 guarantee for 2024-25.
This is what life as a two-way player is supposed to look like, roughly: Start the season just making an impression, hone your craft with a strong G League season, and hope by the end of the year you’re getting some NBA opportunities to show you can be a bench piece the following season. In the case of Freeman-Liberty, he got that contract early, and will have an early advantage in the summer development program and fall-2024 camp battles.
This type of player development success has been a bit rarer for the Raptors in recent years than we’ve been accustomed to.
Never has that been more apparent than the tail-end of a 25-win season. In a year where a team takes an intentional step backward, player development becomes the name of the game.
The Raptors have done a good job continuing to develop good players into better ones. Scottie Barnes took a leap before going down injured. Immanuel Quickley and RJ Barrett have looked ready to expand their roles beyond the ones they had in New York. Gradey Dick’s in-season rehabilitation might be the most important thing that happened this year. Even Gary Trent Jr., who isn’t a prospect based on time in the league and is a pending unrestricted free agent, had a significantly better second half.
Those steps are important. Barnes becoming an All-NBA player or Barrett or Quickley getting to a fringe All-Star level are developments that, if they occur in 2024-25, could change the upward mobility of the team, or at least adjust a murky timeline. Barnes, Dick, Barrett, and Ochai Agbaji are the four youngest players on the roster, save for two-way piece D.J. Carton. Developmental runway for their best players is the single biggest reason for Raptors optimism.
At the other end of the roster, though, it feels like the Raptors are leaving a lost season without any new discoveries. Malik Williams became the 30th player to play for the Raptors this year, and the 32nd to be on the roster (Justise Winslow and Christian Koloko didn’t see game action). That would be a league record for roster churn had the Memphis Grizzlies not topped it already this year. And despite the heavy churn, the Raptors haven’t really discovered someone they didn’t already have in-house.
There are minor successes, to be clear. Mo Gueye playing his way from a G Leaguer to a two-way piece is a nice story for a fun, high-energy prospect who is a little on the older end (he’ll be 26 this summer). Jontay Porter would have been in the same position as Freeman-Liberty had he not been removed from the team as the league investigates irregular betting activity around him.
There’s also been a lot of bad luck. Koloko was waived and referred to the NBA’s fitness to play panel due to a medical issue outside the Raptors’ control and remains sidelined. Ron Harper Jr. was brought back for a second year as a two-way, and while there doesn’t seem to be an NBA player there from what he’s shown with Raptors 905, he was injured for the season and waived before he got a chance to show otherwise. Markquis Nowell was released from his two-way after a long-term injury (which also cost him the G League All-Star Game), too. Carton was signed to fill one of those spots and was immediately injured.
That context is important. Koloko and Porter, in particular, seem like potential player development success stories that didn’t happen through no fault of the Raptors.
Still, for a team that churned 32 players in roster spots this year, it doesn’t feel like anyone except for Freeman-Liberty has popped in their opportunities. Freeman-Liberty (24), Carton (24 this summer) and Gueye (26 this summer) are on multi-year deals. In addition to the injured two-way players, the team also tried Winslow, Jahmi’us Ramsey, Kobi Simmons, and Williams on 10-day deals. It’s possible one of those players factors into summer plans. None were undeniable. Williams will be 26 this summer, anyway. (The team’s other young-ish players don’t offer a much better story; Jordan Nwora (25) is a free agent and is probably headed for a minimum deal as an offence-sparking bench piece somewhere and Jalen McDaniels (26) has taken several steps backward.)
The lack of pop at the end of the roster has been particularly noticeable as former Raptors succeed in bench roles in new locations. Malachi Flynn dropping 50 was as big a red herring as it gets — he’s scored 40 points total for the Detroit Pistons in the four games since — but it felt a bit on the nose the night the Raptors lost their 15th in a row. Dalano Banton has been a major success story since being traded to Portland. Oshae Brissett has played rotation minutes on and off for the league-leading Boston Celtics. Jeff Dowtin Jr. and Justin Champagnie are back in the NBA.
Again, some context is only fair. These things happen around the NBA. Fringe roster players land in new spots and cycle around until something clicks. Garrett Temple had seven different NBA chances and a season overseas before he stuck in the league, and that was before the G League was as well-established. The success rate of 10-days is pretty low, and even in-the-moment successes like Freddie Gillespie don’t always make it through the subsequent summer roster competition. (Of the 43 players to sign 10-day deals in Raptors history, only Alan Anderson and Reggie Slater played for them the following year. Rafer Alston eventually returned but after playing elsewhere.) And the Raptors have done well enough with two-ways, blending win-now players who could help in the short-term like Malcolm Miller, Yuta Watanabe, and Lorenzo Brown with longer-term development plays like Chris Boucher, one of the biggest two-way success stories there is.
Boucher was six years ago now. The lack of a next Boucher highlights a few challenges the Raptors have dealt with. One is that they’re paid the legacy cost, so to speak, of the 2019 championship, armed with fewer draft picks and left to sort through the undrafted bin more often instead. Another is that a split focus between winning now and developing for later is incredibly difficult to execute in real-time, which became one of the key talking points of Nick Nurse’s firing and Darko Rajakovic’s hiring. Mostly, though, in an age where information has never been more efficient for teams, finding undervalued players is difficult, and even the best teams might hit cold streaks, probabilistically.
The Raptors have to hope Freeman-Liberty marks a step back in the right direction. Turning a two-way into a 12th man isn’t as sexy as turning Barnes into an All-NBA player, but it’s the type of developmental success that better equips a team to compete around that All-NBA player. The star-heavy championship core was made possible because the Raptors had desirable prospects to trade and other prospects who were ready to step into supporting roles on inexpensive contracts, a necessity in a salary capped league. Turn an undrafted player into a second-round value, turn a second-round pick into a first-round value, turn a minimum signing into a Bi-Annual Exception value, and those small victories add up, making your team deeper and your roster-building more flexible.
It’s not easy; the Raptors thriving in that area for the better part of a decade was an exception. It’s an exception the front office has shown capable of leveraging, though, and it’s something that could expedite the path back to competitiveness.
