Three Prospects to Watch at No. 39 After Raptors Secure Second-Round Pick

The Toronto Raptors secured the No. 39 pick in the second round where Will Riley, Ryan Kalkbrenner, and Tahaad Pettiford are all expected to be in the mix

Illinois Fighting Illini forward Will Riley (7) rushes past Iowa Hawkeyes forward Payton Sandfort (20) on Thursday, March 13, 2025, during the second round of the men's Big Ten tournament at Gainbridge Fieldhouse in Indianapolis. The Illinois Fighting Illini defeated the Iowa Hawkeyes, 106-94. / Grace Hollars/IndyStar / USA TODAY NETWORK via Imagn Images

The Toronto Raptors secured the 39th pick on Wednesday night thanks to the NBA’s tiebreaker between the Phoenix Suns and Portland Trail Blazers.

It’s a minor win for Toronto, who would have dropped to No. 40 had the draw gone the other way. With the second-round order now finalized, here are three players to watch at pick No. 39, based on recent mock drafts from Bleacher Report, The Athletic, and ESPN.

Will Riley | F, Illinois | 6’8”, 210 lbs, Freshman

Canadian forward Will Riley is one of the more intriguing prospects in this year’s draft and could be a real steal if he slips to the second round. The 19-year-old from Kitchener, Ontario, brings size, scoring touch, and shot creation at 6-foot-8. He has polished footwork, can score at all three levels and plays with a mature tempo for a player his age.

Riley averaged 12.6 points per game as a freshman at Illinois while shooting 32.6% from three and 72.4% from the free throw line. His jumper should develop into a real threat, especially off the dribble, and he looks pretty comfortable operating in one-on-one situations.

There are questions about his defense and playmaking, and he will need to get stronger to finish through contact more consistently at the next level. But for a team like the Raptors, Riley offers real long-term upside as a scoring forward. If he makes strides defensively, he has the potential to become a valuable offensive weapon off the bench in the not too distant future.

Ryan Kalkbrenner | C, Creighton | 7’1”, 260 lbs, Senior

Ryan Kalkbrenner may not have the flashiest profile in this year’s class, but the 23-year-old fifth-year senior offers a dependable skill set that could appeal to the Raptors who are looking for immediate frontcourt depth. At 7-foot-1 with a 7-foot-5 wingspan, the Creighton center is one of the best shot-blockers in college basketball and brings a veteran feel to the game after five seasons in the Big East.

Kalkbrenner averaged 19.4 points, 9.0 rebounds, and 2.7 blocks this season while finishing efficiently around the rim. He also showed some stretch potential, shooting 34.4% from three on 1.4 attempts per game. His free throw shooting remains a weakness, though, as he struggled to consistently convert at the line.

He’s not a switchable defender and lacks the mobility to handle quicker players in space, but in a drop coverage system, he can anchor a second unit and protect the paint without fouling. Kalkbrenner may not have much upside left, but he’s a mature, low-maintenance big who could fill a role from day one.

Tahaad Pettiford | G, Auburn | 6’1”, 180 lbs, Freshman

Tahaad Pettiford is a 19-year-old freshman guard who brings burst, shot-making, and offensive upside in a compact frame. At 6-foot-1, he’s undersized by NBA standards, but his speed and creativity with the ball make him a tough cover. He averaged 9.2 points per game at Auburn and shot 36.6% from three, flashing deep range and the ability to get downhill quickly.

Pettiford plays with confidence and energy, regularly creating separation off the dribble and showing some touch finishing through contact. His size will likely make him a target defensively, and he still has work to do as a decision-maker, but the tools are there for him to grow into a dynamic scoring guard.

For a team like Toronto, he could be a long-term project as a third point guard or Raptors 905 developmental piece. If the defense improves and the decision-making tightens, Pettiford could carve out a role as an offensive spark off the bench.

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