2018 NBA free agency: Biggest winners and losers

Winner: Toronto Raptors
The way the DeMar DeRozan business went down rubbed everyone wrong, but when you can trade for a top-five player in the league (when healthy) without giving up a tantalizing asset like OG Anunoby, Pascal Siakam or an unprotected first round pick, you do it — especially with the King finally abdicating his Eastern Conference throne.
Kyle Lowry is the ideal kind of point guard to play alongside Kawhi Leonard, and though there are concerns about his injury problems and his status as a free agent at the end of the 2018-19 campaign, the Toronto Raptors‘ window was closing. This trade throws it right back open, and if this team manages to win the East and make it to the NBA Finals, it’ll be hard for even Kawhi to bolt for L.A.
Between re-signing Fred VanVleet and this blockbuster trade that really only surrenders Jakob Poeltl and an admittedly beloved star who proved time and time again he wasn’t going to be the difference in the playoffs, the Raptors have to be feeling good. Not only this, but by trading for Kawhi, they also prevented their Eastern foes in Boston and Philadelphia from doing so.
Loser: San Antonio Spurs
On paper, the San Antonio Spurs got an established star for their injured superstar, which is usually as good as you can ask for in a trade with no leverage. Leonard left them in a tough spot, yet they got back DeRozan, a young player with upside in Poeltl and a draft pick.
Anyone trying to sell this trade as a win for San Antonio, however, needs to examine this team’s future prospects. The Spurs may have just added DeRozan to a group that won 47 games last year despite Kawhi missing 73 of them, but they lost their superstar and one of the team’s few floor-spacers in Danny Green.
Replacing them will be DeRozan, whose one notable flaw is his lack of 3-point touch. Pair him with another mid-range savant in LaMarcus Aldridge and a team that was already in the bottom-five for 3-point attempts, makes and percentage last year is going to continue moving away from modern NBA trends. Throw in how the Spurs only got Poeltl and a first-rounder that’s more likely to convey as two second-rounders and suddenly the end of the Kawhi Leonard era becomes even more depressing.