Few moments of the NBA offseason are more exciting than the inevitable changes that happen in free agency.
Unfortunately for many teams, those signings often don't work out as hoped. The last half-decade is loaded with big-money mistakes on players whose salaries far outweighed their actual production.
But the positive side of the conversation is so much better.
The following players all changed teams as free agents since 2019, and they excelled at their next destination.
One important note: The list doesn't include players who re-signed with the previous team or inked an extension, and anyone who signed a max contract is not considered—we're looking for cases where GMs had to dig in an earn their paychecks.
Jerami Grant, Detroit Pistons (2020)
Six years into his career, Jerami Grant had never been a star. He played well in the seasons leading up to his free agency, averaging 13.6 points with the Oklahoma City Thunder in 2018-19 and helping the Denver Nuggets make the Western Conference Finals the following year.
The latter convinced the Detroit Pistons to take a three-year, $60 million risk (in a sign-and-trade) to land Grant.
Despite the Pistons' poor records over the ensuing years, the gamble paid off.
Grant turned in a superb 2020-21 season, averaging a career-high 22.3 points per game and finishing second in Most Improved Player voting. He followed that up with 19.2 points per night in the 2021-22 campaign.
Detroit ended up trading Grant to the Portland Trail Blazers, where he signed a massive $160 million extension last summer. (That contract might not be remembered as favorably.)
Malik Monk, Sacramento Kings (2022)
Malik Monk is a perfect example of a successful prove-it deal.
In four seasons with the Charlotte Hornets, he was a fine complementary player but didn't meet the expectations of his draft billing (No. 11 overall in 2017). Monk bolted Charlotte in the summer of 2021 to sign a one-year, minimum-salary contract with the Los Angeles Lakers, and he was among the few bright spots for L.A. that season.
After rehabbing his value with the Lakers, Monk signed a two-year, $19.4 million contract with the Sacramento Kings in 2022. He continued to improve from there.
Monk averaged 13.5 points and 3.9 assists per game in 2022-23, finishing fifth in Sixth Man of the Year voting. The next season, he put up a career-high 15.4 points and 5.1 assists per game and was the 6MOY runner-up.
Sacramento rewarded Monk's progress with a four-year, $78 million extension during the 2024 offseason.
Alex Caruso, Chicago Bulls (2021)
After becoming a fan favorite and a valuable piece of the Los Angeles Lakers' championship run, Alex Caruso hit free agency in 2021.
While he'd earned respect as a stingy defender and good three-point shooter, Caruso wasn't exactly a must-have player. That allowed the Chicago Bulls to snag him with a four-year, $37 million deal.
The rest of the league undervalued what he would contribute. Caruso secured an All-Defensive selection in both the 2022-23 and 2023-24 campaigns after averaging at least 1.5 steals per game in each of those seasons with Chicago.
Paying one of the NBA's best defenders less than $10 million was an absolute steal for the Bulls. The Oklahoma City Thunder will now get to reap the benefits of that, as they flipped 2021 No. 6 overall pick Josh Giddey for Caruso a few days before the 2024 NBA draft.
DeMar DeRozan, Chicago Bulls (2021)
The summer of 2021 was a busy stretch for the Bulls. Beyond signing Caruso, they also engineered sign-and-trades for both Lonzo Ball and DeMar DeRozan.
While injuries ruined the former deal, the latter worked out great for Chicago.
DeRozan, who agreed to a three-year, $81.9 million contract, poured in 27.9 points per game during his debut season with the Bulls. As the franchise snapped a four-year playoff drought in 2021-22, he earned an All-Star nod along with second-team All-NBA honors.
Chicago fell short of the postseason during the next two years—Ball playing zero games in either one didn't help in that regard—but DeRozan averaged 24-plus points per game in both seasons and landed another All-Star trip in 2022-23.
Bruce Brown, Denver Nuggets (2022)
At least through the 2023-24 season, Bruce Brown is the single most impactful player on the list in one respect.
Brown split his first four years in the NBA on the Detroit Pistons and Brooklyn Nets, and then he signed a two-year, $13.2 million deal with the Denver Nuggets in 2022. That contract included a player option after the first season.
Brown was nothing but a bargain for the NBA champions. He held a critical role as the Nuggets' top backup.
Brown was Denver's only bench player who averaged more than 4.1 points in the playoffs in 2022-23. He netted 12.0 points per game, with especially important games in the second round against the Phoenix Suns and opposite the Miami Heat in Game 4 of the NBA Finals.
As expected, he opted out of that contract last offseason and landed a two-year, $45 million payday from the Indiana Pacers.
Jalen Brunson, New York Knicks (2022)
Relative to production, there is little debate that Jalen Brunson is the most notable player highlighted here.
The Dallas Mavericks originally selected Brunson with a second-round pick in 2018. He developed into a guard who flashed upside as a core scorer when Luka Dončić was sidelined in 2021-22.
However, the Mavs slow-played contract negotiations and ultimately lost Brunson for nothing in free agency. The New York Knicks signed him to a four-year, $104 million contract in 2022.
Dallas' loss—a mammoth one, in hindsight—has clearly become New York's gain.
In two seasons with the Knicks, Brunson has averaged 26.5 points and 6.5 assists per game. He finished third in Most Improved Player voting in 2022-23 before receiving his first All-Star trip, a fifth-place finish in MVP voting and second-team All-NBA recognition in 2023-24.
Brunson has a $25.0 million player option in 2025-26 that he figures to decline. The Knicks can offer him a four-year, $156 million extension later this summer, but he'll be eligible for a five-year deal worth up to nearly $270 million if he decides to test the free-agent waters next year.
Donte DiVincenzo, New York Knicks (2023)
The third member of the Villanova Knicks next to Brunson and Josh Hart, Donte DiVincenzo had a breakout year in his debut with New York.
DiVincenzo bounced around the NBA for a brief stretch, leaving the Milwaukee Bucks as part of a 2022 deal at the trade deadline. He played out the rest of that season on the Sacramento Kings, spent the ensuing season in Golden State and inked a four-year, $46.9 million contract with the Knicks in 2023.
So far, so very good.
The sharpshooter scored a career-high 15.5 points per game during his first season with the Knicks, shattering his previous high of 10.4 points. DiVincenzo launched 8.7 three-pointers per night and buried them at an elite 40.1 percent clip.
He stepped into an even larger role for the injury-plagued Knicks in the playoffs and averaged 17.8 points per game across their series against the Philadelphia 76ers and Indiana Pacers.
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