As Kyle Lowry approached free agency for the second time as a Raptor back in 2017, it seemed possible he would get a deal close to a maximum-value contract.
Lowry was coming off arguably his best two seasons in the league. In 2015-16, he recorded 11.6 win shares, and followed up with a 10.1-win share season — in just 60 games. Those are two of the top eight Raptors seasons by that metric (Lowry has posted four of the eight 10-plus-win-share seasons for the club). He was halfway through his six-season run as an All-Star, a clear difference-maker when it came to winning basketball games.
Alas, the Raptors were swept by the Cavaliers in the second round that year, with Lowry missing the last two games with an ankle injury. He averaged just 14.3 points and 5.2 rebounds per game against the Bucks in the first round, with an ugly shooting line of 42.6/25/79.1 percent.
