Just six games in, the Toronto Raptors are already off to a bumpy start with a record of 3-3. With All-Star forward Kawhi Leonard on the shelf with a knee injury for the next 3-4 weeks, the Raptors must continue to stay afloat and maintain stability amongst the top half of a strong Eastern Conference.

Although Toronto has surprisingly sits amongst the top-10 teams in scoring (9th, 118.3 point per game), their biggest hole offensively continues to be their lack of three-point accuracy. The Raptors are shooting 32 per cent, 7th worst in the NBA. With minimal shooting on the roster, the team may have to look to the trade market to make the fix. According to CBS Sports NBA writer Sam Quinn, Milwaukee Bucks guard Tyler Herro may be the perfect candidate to target first.

Why It Makes Sense for the Raptors

It’s no secret that the Raptors current backcourt has been a major question when measuring this team versus the league’s elite. In the shooting department Immanuel Quickley is a knockdown shooter (37.4 per cent for his career) but can be a streaky scorer with size that creates doubt about how he will hold up against the physicality that comes in the Playoffs.

His lack of consistency on offense paired with his underwhelming potential defensively led to him being cast away from the New York Knicks and could eventually be costly to future Raptors playoff run.

Barrett on the other hand is the exact opposite equally problematic. Barrett has been a consistent 18 to 20 point scorer throughout his career with a bit more upside defensively standing at 6-foot-6. The issue is that he’s not a good three-point shooter (29 per cent this season) and needs the ball in his hands to be the most effective. On a team with better ball handlers like Leonard, Scottie Barnes and even Quickley, his on-ball talent is outweighed by his need to help in the floor spacing department.

Herro is a happy medium between the two. Herro has averaged 20 or more points each of the last each of the last six seasons, including averaging 22 points through six games so far with the Bucks.

At 6-foot-5 he has the upside to be a better defender then Quickley and as career 38.3 per cent three-point shooter on just over seven attempts per game, he provides the floor spacing that Barrett hasn’t. But more importantly, through his time with the Miami Heat, he has learned how to be just as effective off-ball as he is on the ball. An overall better fit role wise with All-Star production to match.

Do the Raptors Have Enough to Push the Deal Through?

Honestly with Herro making $33 million as an expiring deal and Barrett making $29.6 million and also expiring, the deal could be a perfect one-for-one swap with pick attached to Barrett to incentivize the Bucks to give up the better player in the deal.

It’s also notable that the Bucks have a ton of guards with rookie Brayden Burries, Ryan Rollins and Kasparas Jakucionis headlining a promising backcourt rotation. Getting some kind of value for Herro while opening up more minutes for the younger players to see the floor maximizes his value.

Also with Kyle Kuzma as an expiring contract and Jaime Jacquez Jr. set to hit restricted free agency next summer, the Bucks’ forward rotation gets a little thin with only Ousmane Dieng and rookie Nate Ament to fill the roles. As someone who could slide to the three, Barrett could be a re-sign candidate if Milwaukee gets outbid for Jacquez Jr.

The worst case scenario is Barrett walks and the Bucks still come out of the trade with draft capital rather than a result where either Herro or Barrett could simply just leave in free agency this summer. Given that Herro has easily been their best player so far this season and the “hometown kid” element, the Bucks may simply value Herro too much to move him for such a small package. But Herro’s pending free agency could hinder Milwaukee from getting any offers better than what Toronto could offer.

Nonetheless, a trio of Herro, Barnes and Leonard with players like Ja’Kobe Walter, Collin Murray-Boyles, Jakob Poeltl is a strong lead six to spearhead an eight-man playoff rotation. The fit is nearly perfect, it just comes down whether the Raptors are willing to part with a draft pick to make it happen.