Both players are unrestricted free agents and should draw interest from contenders and teams looking to make significant changes.
They could be the premier names on the market if Anthony Davis, Gordon Hayward and Andre Drummond opt to remain with their current teams and the New Orleans Pelicans do everything to keep restricted free agent Brandon Ingram.
Gallinari drew interest from the Miami Heat at the trade deadline, and there is still a chance the two parties unite when the season concludes.
VanVleet should have a variety of suitors, including at least two from the Eastern Conference that are looking to leap up the standings.
Free Agents Who Could Switch Teams
Gallinari's best two-season span of his career is one of the factors that could lead to leaving Oklahoma City in the offseason.
The Italian forward averaged a career-best 19.8 points per game last season and has 19.2 points per contest in the current campaign.
In that span, Gallinari's three-point shooting has improved, as he shot 43.3 percent in 2018-19 and 40.9 on a higher number of three-point attempts this season.
Gallinari would be a valuable asset for any contender if he left the Thunder, who may not be able to match his asking price if the salary cap decreases, as The Athletic's John Hollinger pointed out:
"If the Thunder entertain ideas of keeping Danilo Gallinari at a price point in the $20-25 million range, a lower tax line makes it a lot harder. Not impossible, but harder. One presumes they’d like to use their full mid-level on a younger wing and that they also would wish to keep Nerlens Noel; doing all three would push them well into the tax and invoke a punishing repeater penalty."
The natural connection to make for Gallinari is the Miami Heat, who tried to acquire him at the trade deadline, as Heat president Pat Riley told Ira Winderman of the South Florida Sun-Sentinel.
"I like Gallo. And I think he would have fit in here really well, but it didn't work out. And somewhere you have to sort of draw a line in the sand for your team," Riley said.
If Miami still has interest in Gallinari, it has to weigh how long it wants to keep him around to partner with Jimmy Butler.
Gallinari is making $22.5 million on the back end of his current deal and likely would not be a cheap option on the open market.
The ideal move for the Heat would be to sign him to a short-term deal so the player can get maximum value for himself while the team does not get stuck with a longer contract for a guy in his 30s.
That would also allow Miami to chase bigger free agents in the coming years without limiting their financial capabilities.
VanVleet is due for a pay increase after improving his scoring average by six points per game in his fourth NBA season.
The guard out of Wichita State is averaging 17.6 points and 6.6 assists per contest and is shooting 40.9 percent from the field and 38.8 percent from three-point range.
Toronto should do its best to keep him around as the long-term solution at point guard as Kyle Lowry gets older, but the Raptors may not be able to retain his services.
The Athletic's Danny Leroux expects VanVleet to garner a contract much higher than the two-year, $18 million deal he is currently on: "It feels like he will get about $15 million to $18 million per season, but contract length will be key."
The Detroit Pistons and New York Knicks are among the suitors that could chase VanVleet in the offseason.
Detroit needs to find a younger point guard to take over for Derrick Rose, and the Knicks need help at every spot on the hardwood.
New York could be more inclined to land a premier free agent in 2020 after striking out on the big names in 2019.
That would give the Knicks a small foundation to work off when they begin to make their pitches to the more robust free-agent class of 2021.
The Pistons and Knicks could both opt to focus on point guard in the draft with so many prospects available at the position, but signing VanVleet away from Toronto may be the more intriguing option since he is a known commodity compared to rookies that would time to adjust to the professional level.
Detroit and New York could be among the suitors for Evan Fournier as well.
The 27-year-old shooting guard has a $17 million player option for the 2020-21 campaign, but he may turn away from the Orlando Magic.
Although salary cap space is limited across the league, Fournier could be in the best position to cash in on his talents now.
He is averaging a career-best 18.8 points per game and is close to his best-ever three-point shooting percentage (40.7) at 40.6.
While it is possible Fournier improves his numbers again next season and earns a large contract, he may not want to take that risk.
That leaves him with one of the most difficult decisions of the offseason, but if he leaves, he should have a handful of potential suitors.
If Fournier believes the risk is worth it, he could find some long-term security on a deal that might fetch something similar to what he would under a player option in Orlando.
Follow Joe on Twitter, @JTansey90
Statistics obtained from Basketball Reference
Contract information obtained from Spotrac