With how long the Kawhi Leonard trade took to become official, it may sound silly to some to be drawing up mid-season trade angles for the Toronto Raptors. But it’s September, and after minimal news and typing my fingers off about whether Leonard was or wasn’t coming to Toronto for two-plus months, I want to change things up. Since Leonard’s return was made official, one of Toronto’s players whose future was dragged back into the limelight has been RJ Barrett.
Some fans have started asking whether Barrett is good enough defensively and off the ball offensively to fit as a starter with this team. For some time now, I’ve made my stance clear: no. With that, I hopped on the trade machine and started cooking things up, eventually landing on Jrue Holiday as the perfect trade target.
Now, I’ll say this: I don’t see Portland wanting Barrett, and you’d likely have to get another team involved because Toronto is currently hard-capped and can’t aggregate contracts in trades. But with their guard depth and Holiday having a player option for $37-plus million next summer, I see a real possibility he is dealt before the 2027 trade deadline. So if the Raptors can find a way to make the financials work, getting Holiday would be a no-brainer.
Holiday could be the missing piece
While I have argued that trading Barrett for an upgrade isn't the path Toronto should take and instead should stretch his salary into two rotation players, Holiday is different. Sure, Holiday is an upgrade, but he’s also a great fit for this team. Holiday would be another proven, experienced winner who is still elite defensively and has thrived off the ball in the later half of his career.
For the Trail Blazers, Holiday averaged 16.3 points, 4.6 rebounds, 6.1 assists, and 1.0 steal per game last season, while shooting 37.8 percent from three in 53 games. That type of well-rounded production off the ball in the backcourt next to Immanuel Quickley would be a match made in heaven for Toronto. Holiday would be a plus floor spacer, high-level connective passer, a very good rebounding guard, someone who can play in the dunker spot and is a pitbull on the defensive end.
Think about a late-game situation where you're up three with two minutes to go and need stops to close out the game. So what lineup does head coach Darko Rajakovic roll out? Holiday, Ja’Kobe Walter, Leonard, Scottie Barnes, and Collin Murray-Boyles. I mean, talk about clamps city. Holiday and Walter picking up 94 feet with CMB in the paint and Leonard and Barnes wreaking havoc on the wings sign me up.
Although the financial burden of a deal like this is real and is why trading Barrett for two players is likely an easier route, Holiday would put this team over the top. The winning characteristics in his game and the experience he has as a two-time champion would be a natural fit for this roster. So definitely keep this idea in mind as we get into the regular season.
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