Fred VanVleet is at a crossroads in his career. With the Raptors struggling to even make it into a play-in spot, they may soon find themselves willing to deal away a few crucial members of their core.

Among the Raptors’ core players, however, VanVleet appears to be one of the likeliest to go, especially with his upcoming foray into free agency in a few months time should he decline his player option for the 2023-24 season. And one rumored suitor – the Orlando Magic – is already planting the seeds for a potential Fred VanVleet arrival.

A member of the Magic front office was in attendance during the Raptors’ 130-122 loss to the Milwaukee Bucks on Tuesday night, per Michael Grange of Sportsnet Canada. At the very least, VanVleet definitely impressed that executive with his 39-point performance even if it didn’t result in a victory.

The Magic have reportedly expressed interest in, not only a potential free-agent pursuit of Fred VanVleet, but also a potential trade should the Raptors’ season continue to go south. And in the process of doing so, they appear to have taken a page out of the Los Angeles Clippers’ playbook, who courted Kawhi Leonard by also sending a few executives to Raptors games.

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Orlando currently has a few point guards in their ranks, namely Markelle Fultz, Cole Anthony, and last year’s fifth overall pick, Jalen Suggs. Fultz, in particular, looks like a true keeper, emerging as a solid two-way playmaker even if his shooting hasn’t truly developed as well as one would have hoped. Nonetheless, the Magic look ripe for a consolidation of talent, with too many players clogging up a few positions.

Thus, it makes sense for the Magic, especially as they look to expedite their rebuild to pursue an All-Star guard in Fred VanVleet to bolster the squad around Paolo Banchero and Franz Wagner. They have the necessary assets as well to swing a trade, should the opportunity arise before the February 9 trade deadline.

However, it may be shrewd for them to wait until free agency commences, since they can most definitely free up the necessary cap space to sign the 2022 All-Star. And if sending an executive to watch Raptors games is any indication, that may be the route they’re willing to take.