Kyle Lowry and the Raptors have experienced their best years together, taking Toronto to heights it had never seen before. But while their success was groundbreaking, the star point guard might still be on his last leg.

Last season marked a seminal moment for the Raptors, with Toronto claiming the East’s best record for the first time in franchise history. Armed with one of the league’s most effective bench mobs, the duo of Kyle Lowry and DeMar DeRozan reached new heights, with the latter earning second-team All-NBA honors. With a vulnerable Cavs squad and banged-up Boston as their chief competition, 2017–18 looked to be the year for Toronto’s first-ever Finals appearance.

LeBron James had other plans. The King steamrolled the Raptors in the Eastern Conference semifinals, sweeping Toronto out of the playoffs. The beatdown was so severe it sent seven-year head coach Dwane Casey packing, ending the run of the most effective coach to ever stroll the sidelines in the Six. Raptors president Masai Ujiri followed through on his calls for a “culture reset”, albeit one year later than expected.

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It’s not just the coaching staff that will be new up north next season. Toronto opted to buy a one-year lottery ticket on disgruntled Spurs’ star Kawhi Leonard, shipping the homegrown DeRozan to San Antonio. After years of carefully growing its core from Eastern irrelevance to perennial contender, Toronto has entered a new phase: Finals or bust.

With DeRozan in the Lone Star State, Lowry is now the longest tenured Raptor, which is emblematic of the franchise’s rise through the East. He entered Toronto in 2012 after three-and-a-half year stints in Memphis and Houston, a useful yet unspectacular backcourt piece. Since then, Lowry has ripped off four-straight All-Star appearances, earning All-NBA honors in 2015–16. The former overweight point guard from Villanova has become one of the NBA’s leading floor generals.

Pairing with Leonard will be Lowry’s best shot at capturing the elusive conference crown. DeRozan’s inability to shoot from beyond the arc—save for flashes of effectiveness last season—limited Toronto’s spacing, relegating Lowry to a catch-and-shoot role in key moments. The pair failed to play off one another, rotating isolation possessions reminiscent of early Wade-LeBron and Durant-Westbrook come playoff time.

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And with neither player skilled enough to truly take over down the stretch, Toronto’s offense became a stagnant mess against the Cavaliers, failing to generate quality looks late. Lowry registered just five points in Toronto’s Game 4 blowout loss to Cleveland, while DeRozan shot 34.8% in the final two contests. It was an ignanamous end to the best season in franchise history.

Lowry’s struggles against Cleveland were disappointing, but they weren’t entirely surprising. The 13-year veteran entered the 2017 playoffs with the worst field-goal percentage amongst all active players in playoff competition, currently sitting at No. 9 on the list. Toronto entered the 2018 playoffs losers of 10-straight Game 1’s, seven of which with Lowry at the helm. It’s never an encouraging sign when your franchise point guard says, "Our Game 1 is our Game 7 tomorrow,” when referring to a first-round matchup with the Wizards.

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If the acquisition of Leonard marks Lowry’s best chance at reaching the NBA Finals, it also might mark his last in Toronto. The Raptors’ brass signaled it was frustrated with the status quo in the firing of Casey and trade for Leonard. With the clock ticking until Leonard’s free agency next July, a strong showing in the East won’t be enough. Anything short of the Finals won’t suffice. Another season of falling short, and Lowry could very well be on the way of Casey and DeRozan, out the door and on a plane back to America.

The pieces are in place for a clean break should Toronto fail to capture the East and see Leonard chase a new situation in free agency. Lowry will be an expiring contract in 2019–20, and while he’ll come in at an expensive $33 million, he can still be a valuable piece for a contender, a minimal risk with no additional years attached. Even if Toronto doesn't find a taker for Lowry’s deal, 2019–20 will be seen more as a farewell tour than a career revival. Lowry will be 34 at the end of his contract. Another three-year, $100 million deal like the one he signed in 2017 won’t be on the table.

Aside from the economics of parting with Lowry, Toronto is in prime position to reset without its veteran cornerstone. The Raptors sport a treasure chest of promising youngsters, heavy on wing talent. OG Anunoby shined as a two-way menace in his rookie season out of Indiana, while Pascal Siakam flashed as an impressive rim runner and stretchy defensive pillar. Fred VanVleet is wise beyond his years slinging passes off the pick-and-roll with Jonas Valanciunas, and Delon Wright is a reliable three-point threat. The kids were alright when Lowry headed to the bench last season.

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Toronto’s bet on Leonard was a sensible play, born out of frustration from the good-not-great years of the Lowry-DeRozan pairing. The former Finals MVP will be the best player to ever suit up for the Raptors, capable of running roughshod through the East playoffs with Lowry as his sidekick.

If all breaks right for Ujiri and Co., Leonard will win the conference and fall in love with Toronto, signing long-term for a half-decade of competition with Boston and Philadelphia. But if the Raptors do fall short and see Leonard head west, there is still a path to relevancy moving forward into 2019–20. It just won’t include Lowry.