Will the Toronto Raptors ever make it back to the NBA Finals?

With the NBA Finals now underway, and our Toronto Raptors long gone from the Orlando Bubble, I can’t help but wonder: was 2019-20 their best chance to get back to the Finals?

And since they didn’t make it back there, that leads to: Will the Raptors ever make it back to the NBA Finals? And when?

If 2018-19 taught us anything, it’s how difficult it is, and how lucky a franchise like the Raptors (read: Not a warm-weather, big U.S. market, hi Lakers and Heat!) must be, to get to the Finals. The Raptors needed a superstar to get injured and lose trust in his (highly respected!) organization, had to have the right assets to trade for him, had to remain good enough to win when he sat out for load management and needed four bounces to get out of the second round.

When I look at this completely bizarre 2019-20 season, it seems like the Raptors may have blown a prime opportunity. The four-month break, plus the lack of travel, was a boon to a an older team that was beset by injuries all year. And after playing pretty well in the seeding games, they got the best possible first-round playoff matchup. Their defense seemed tailor-made for the playoffs.

And while the Raptors fought it out with Boston, the top seeded Bucks were losing to the fifth-seeded Heat. Which makes me feel that the Raptors blew a great opportunity to get back to the NBA Finals.

Obviously I don’t know that the Raptors would have beaten the Miami Heat; they’re flawed, but they’re good, well-coached and tough, and they’d beaten the Raptors two out of three times this season. But I think the Raptors would have had a good chance — especially if Pascal Siakam managed to shake off his slump — and I think they’d have put up a better fight than the Celtics did. (And I don’t need to tell you to the Raptors were 2-0 against the Lakers this year, right?)

Alas, Toronto could barely hit a shot against Boston, Siakam struggled mightily on offense, the bench disappeared and the Raptors lost to the Celtics in seven games.

Which means we’re watching other teams in the Finals — and looking forward for the Raptors.

How Far Will the 2020-21 Raptors Go?

It’s possible, depending on how free agency shakes out, that the Raptors run it back with their same core seven guys, if Fred VanVleet returns and Serge Ibaka and Marc Gasol take one-year deals to stick around. If VanVleet and Siakam continue to improve, if OG Anunoby, Terence Davis and Matt Thomas continue to develop, and if Kyle Lowry remains Kyle Lowry, sure, next year’s team might have a shot. (Though of course the Bucks, Celtics, Heat and 76ers will have something to say about it).

Chances are, though, that next year will be a transition year for the Raptors, as they look ahead to 2021 free agency, which is where many of us have our hats hung as the real path to the Raptors remaining in title contention.

But while this “We the North”-era iteration of the Raptors is better poised than ever to lure a big-name free agent, I’m still a “believe it when I see it” guy. It’s never happened. I hope it does! But what if it doesn’t?

Let’s also consider the future of Masai Ujiri with the Raptors. He still hasn’t signed a contract extension (and neither has Bobby Webster, despite Masai saying that deal was “close” two weeks ago). If Ujiri becomes a free agent right when 2021 free agency opens, that’s a disaster; he’s part of the draw of coming here, for one thing, but also, if Ujiri is planning to leave, is he even going to be recruiting free agents to come here at all? Or will he be forging relationships with an eye on his next job?

What are the Raptors’ Chances in 2021-22?

So with that in mind, there’s a possibility that the 2021 Raptors — if they strike out on free agency, and if Fred VanVleet signs elsewhere this offseason and Kyle Lowry signs elsewhere in 2021 or retires, and if Ujiri isn’t around to mastermind the next step — will be closer to the middle of the pack than the top, and without a proper path forward to improve.

And that does make me think we might not see the Raptors back in the Finals for a long time, if ever. The big market teams, after all, will keep getting richer, and big-name players will want to play for those teams (many without bothering to wait for free agency). Small market teams will have to continue to wait for lucky breaks that may never come.

That makes me a little sad, certainly. It also makes me even more grateful for the 2018-19 season.

The further we get from it, the more and more unlikely — and amazing — the Raptors’ 2019 championship becomes. While it feels like 24 years was a long time to wait, I also can’t help but think of the other teams that have never made it to the Finals, like the Hornets and Timberwolves, who are working on 30-year droughts. Or the Bucks, Wizards, Hawks, Kings and Nuggets, none of whom have been to the Finals in four decades or more. Or of course, the Clippers, who in 50 years have never even been to the Conference Finals.

Anything can happen, of course. Maybe I’m wrong about the Raptors’ future chances; maybe that Raptors schadenfreude-bred pessimism still lingers. Maybe those lucky bounces come our way again (or maybe they come for one of those other long-suffering fanbases)!

All we can do is hope, put our faith in the team’s management, and utter those infamous words: “maybe next year.”