During a media availability, Webster indicated he's optimistic about keeping the relationship between team and player going, telling reporters that "everything has been positive" so far.
"I think we’ve said it publicly, privately and every which way. He’s our top priority, he’s our biggest priority for the off-season is bringing him back," Webster said. "He had a great run four years, we fully expect that to continue and everything’s been positive."
VanVleet, 26, is scheduled to hit free agency when the market opens this Friday and will be one of the biggest names available. The guard went from undrafted signee in 2016 to G-League champion one year later with Raptors 905, and then made the jump from grind-you-down member of the Raptors' bench mob in 2018 to Championship starter in 2019. Asked about his goals as a first-time big-name free agent during an appearance on The Old Man & the Three podcast last week, VanVleet was an open book:
"I'm trying to get paid, man,” hosts JJ Redick and Tommy Alter. “I'm not shy about that. I don't have to tell people that I value winning. Just look at my story, do your research. I've never been on a losing team in my entire life. That's what I'm about. And that's just what it is. I won a championship and now it's time to cash out.”