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The Anguish Index: Every post-2014 Raptors playoff game ranked — #51-26

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We’re looking back over the past five years of Raptors’ post-seasons to determine a definitive ranking for each and every playoff game based on how much it sucked to watch it. Welcome to the Anguish Index.

NBA: Playoffs-Miami Heat at Toronto Raptors Nick Turchiaro-USA TODAY Sports

The last five years in Toronto basketball have generally been fruitful and fun. More often than not, though, the endings of those seasons have been downright miserable. We don’t need to re-litigate all the different reasons why the Raptors have pooped the bed in the playoffs time and again. LeBron did some mean things; Paul Pierce can go to hell; Kyle and DeMar had a lot of 4-of-19 games. You know the repetitive, soul-crushing drill.

All those heartbreaks hurt, but they were also necessary. Each Game 1 misstep or lifeless sweep served as a step along the road to the 2018-19 season — the year where, finally, there is no need to be cripplingly afraid of spring hoops. At least, there probably isn’t.

The Raptors have Kawhi Leonard now. It actually is different this year, because he is different.

It’s not as if Raptors fans won’t suffer any despair in this year’s post-season. Sorrow is inherent to every team’s run, save for one. But with Leonard, and Danny Green, and Marc Gasol, and new Pascal Siakam, and all the other good players these Raptors employ, the agony should be sparse relative to years past. There’s reason to be confident — even arrogant — about what this Raps team is about to do.

So with hopefulness in the air, and a first round date with the Magic finally set in stone, let’s reflect on five years of pain. Closure is important in the quest for growth.

Here is every playoff game the Raps have played since 2014 — considered in total as the We the North-era in Toronto — ranked from least to most crushing. Let the sadness wrap itself around you like a heated blanket, baby.

Unbridled Joy

There have been, by my count, three Raptors playoff games since 2014 during which I do not recall feeling an ounce of stress. Three times where Raps fans were able to fully embrace the Hakuna Matata lifestyle. Let’s get ‘em out of the way quickly.

#51. 2016 — Round 3, Game 3 — CLE 84, TOR 99 / The Bismack Game

Game 3 of the Eastern Conference Finals against the Cavs didn’t feel especially heavy. Toronto’s championship was simply making it to round three. Getting booted in the gut twice to open the series erased any illusions that the Raptors might actually win the thing. The first ever conference finals game at Air Canada Centre had more of a celebratory, happy-to-be-here vibe. And then the Raptors went out and kicked the piss out of Cleveland!

It was one of the rare post-season games where both Kyle Lowry and DeMar DeRozan played up to their abilities in concert; KLOE with a tidy 20-6-3 on 4-of-8 from deep, DeMar with a steadying 32 on 24 shots. Bismack Biyombo grabbed the 26 most noise-inciting rebounds this city has ever seen. It was a perfect victory, free of lofty expectations or, let’s be honest, real stakes. The same could not be said for the game that followed it. More on that tomorrow.

#50. 2018 — Round 1, Game 6 — TOR 102, WSH 92 / Extinguishing The Wizards

Closing out the Wizards in 2018 was so goddamn sweet, dude. The Game 6 win, in which Lowry had himself a game, the 2015 sweep demons were exorcised, and Delon Wright blocked the shit out of Kelly Oubre Jr. as time expired, warmed the tummy like a hot, artisanal chai.

#49. 2016 — Round 2, Game 7 — MIA 89, TOR 116 / The Kyle Lowry Middle Finger Game

And then there was Game 7 against the Heat. That one sure made you feel squeamish in the lead-up to opening tip. But all those frayed nerves just kinda washed away over the course of the game. Toronto didn’t pull away for good until it picked apart Miami with a 30-11 fourth quarter push, but Kyle freaking Lowry, man — he had his finger on the pulse of the entire contest. He was not losing that game, and he made you believe it from the jump. Lowry’s final line — 35-7-9 on 11-of-20 shooting, 5-of-7 from deep, and a game-high +31 — stands as Toronto’s best individual playoff performance of the last five years, I think. Even more importantly, the game brought Yonge-Dundas Tupac into our lives.

Stunning Subversions of Expectations

#48. 2018 — Round 1, Game 1 — WSH 106, TOR 114 / THEY WON A GAME ONE!?!?!

No seriously! They won a Game 1! Delon Wright and CJ Miles, at least for a little bit, made the dream of a sustainable playoff bench still believable!

No Game 1 could ever be considered an anxiety-free affair. Toronto is 2-13 all-time in series-openers, and this one was just a one-point game going into the fourth. But it’s hard to match the relief of winning that game, man. No exhale has ever been more prolonged.

#47. 2018 — Round 1, Game 2 — WSH 119, TOR 130 / They Have a Two (2) Game Lead?!

For a brief moment in time, it looked like the Raps might strike back at the Wiz with a four-game series win of their own. Of course, it was the Raptors in the playoffs so the sweep was never actually going to happen. But those couple days sure were sweet.

#46. 2017 — Round 1, Game 5 — MIL 93, TOR 118 / The Game Where They Proved They Solved It

#45. 2017 — Round 1, Game 4 — TOR 87, MIL 76 / The Game Where They Solved It

Toronto’s collective sphincter has never, ever been tighter than it was in the run up to Game 4 against the Bucks. Two big deadline moves, all sorts of looming free agents, the prospect of going down 3-1 to an emergent, narrative-backed Giannis — the stakes have rarely been so high in Raptors history. Aside from indigestion, the only certainty about Game 4 was that Dwane Casey was going to have to do something to change the tenor of the series.

Maybe it took him a few games too many to get there, but Casey solved the Bucks with a single lineup move in Game 4. Jonas Valanciunas out, Serge Ibaka to the five, DeMarre Carroll to the four, Norman Powell in on the wing: Check mate. Bless you, Jason Kidd, you wonderful dolt.

Game 4 wasn’t entirely smooth. Serge nearly shot the team out of it in the opening minutes of the fourth quarter until Casey deftly yanked him. But it was the symbolism of Norm canning treys and driving sharply to close out pretty, flowing possessions that ultimately lands Game 4 among the most easy-to-enjoy post-Gay playoff games.

I probably could have stuck the Game 5 blowout in the first group. That was a wire-to-wire pounding that proved the Bucks were out of moves to make. Blame thematic convenience for its position here.

#44. 2016 — Round 3, Game 6 — CLE 113, TOR 87 / A Fight Well Fought

Everyone knew the series was over going into Game 6 of the Conference Finals. Shit, Luis Scola couldn’t even pretend:

After shelling the Raps in Game 5 (we’ll get to that game, don’t worry), LeBron dropped the hammer quote:

“I’ve been a part of some very adverse situations. And I just didn’t believe that this was one of them.” That’s it. That’s what ended the series.

Even if the Raps had pushed it to seven with a home win, there was no way Toronto was taking a deciding game at Predatory Loans Arena. Better to get a proper send off from the home crowd after valiantly fought series, anyway. And boy did they ever receive that. Toronto fans rule in victory; but they’re just as devoted in honourable defeat.

#43. 2018 — Round 1, Game 5 — TOR 108, WSH 98 / OK! Back on Track!

Any win over the Wizards is gonna rank pretty high.

#42. 2014 — Round 1, Game 2 — BKN 95, TOR 100 / The First Win Since ‘08

None of the games against Brooklyn were exactly chill. All but one were decided by eight points or less. It’s kind of hard to feel relaxed with Kevin Garnett roaming the floor, no matter the score. But Game 2 against Brooklyn gets bumped up a tier because it was the Raps’ first post-season win since 2008, and it was glorious.

Sort of Happy Sighs of Relief

Ah, now we get into the games that weren’t so much enjoyable as they were not entirely horrendous and gut-wrenching. Fun!

#41. 2016 — Round 2, Game 5 — MIA 91, TOR 99 / DeMar! Ya Did it Buddy!

Deebo had one of his very playoff games as a Raptor to edge his team ahead of Miami, 3-2. Just imagine his career playoff shooting numbers without the 34 points on 11-of-22 he posted that pivotal fifth game. The game also provided the most aesthetically pleasing sequence of the ugliest series of the decade. Bismack was a glimmering light in the enveloping darkness.

#40. 2014 — Round 1, Game 4 — TOR 87, BKN 79 / It’s Goin’ Long!

Probably the grimiest game of the 2014 first round. Holding Joe Johnson to seven points on 2-of-7 shooting over 42 minutes is a landmark achievement for the franchise. John Salmons: not entirely useless!

#39. 2016 — Round 1, Game 3 — TOR 101, IND 85 / Disaster Actually Averted?

#38. 2016 — Round 1, Game 2 — IND 87, TOR 98 / Disaster Averted... For Now

A 56-win, second-seeded Toronto team lost a Game 1 to a team that started Lavoy Allen at power forward...

This series was agonizing, start-to-finish. The two games where it looked like the Raps had figured Indy out were just the least stomach-churning.

#37. 2016 — Round 2, Game 3 — TOR 95, MIA 91 / The Game Where Jonas Went Down

It is hella telling that one of the 15-most pleasant playoff experiences of the last five years featured a series-ending injury for Toronto’s best player to that point in the 2016 playoffs. With Hassan Whiteside going down a couple quarters earlier, the series lost its lone compelling head-to-head match-up in one fell swoop. It’s the first and only time the Heat have been less fun with Whiteside on the bench. This series was ass. Thank god for Lowry’s 33 points.

#36. 2017 — Round 1, Game 2 — MIL 100, TOR 106 / They Will Never Lose a Game Two Again

It’s a shame we’ve never been able to revel in the Raptors’ Game 2 dominance, what with all the existential dread and sweating all the Game 1 pants-shittings have caused. This Game 2 was back-and-forth for three quarters before the Raps finished strong in the fourth. Lowry and DeRozan combined for 45 points on unseasonably warm 50 percent shooting, and Giannis managed to go just 9-of-24. A solid win that helped stave off widespread panic, at least for a couple days.

I Don’t Feel Anything Anymore

#35. 2017 — Round 2, Game 4 — CLE 109, TOR 102 / Hey! They Tried Really Hard!

Ah, the classic viking funeral game to wrap up a convincing sweep. At least in this one the Raptors tried kinda hard. Down Lowry — who may or may not have been able to play but didn’t cause of his pending free agency (???) — Cory Joseph had himself a 20-point, 12-assist, six-rebound game on 8-of-11 shooting in his final game with his hometown team. That’s about all the cheer I can spread. This series was the slowest possible quick death.

#34. 2018 — Round 1, Game 3 — TOR 103, WSH 122 / Eh, They Were Always Gonna Take One

Any loss to the Wizards is a great tragedy. Every ounce of success achieved by John Wall and Bradley Beal and The Bad Morris is an assault on the concept of meritocracy. But I mean, you didn’t actually think the Raps were gonna pull of a sweep, did you? At the time, it felt like a harmless loss not worth bunching your knickers over.

#33. 2017 — Round 2, Game 3 — CLE 115, TOR 94 / Shoulder Shrug

No Lowry, no fight, all of the alcohol. Screw this series.

Mid-Series Annoyances

#32. 2016 — Round 2, Game 2 — MIA 92, TOR 96 (OT) / This is Going to Be So Ugly

#31. 2016 — Round 2, Game 4 — TOR 87, MIA 94 (OT) / Please Poke My Eyes Out

There were no wins in the 2016 second round; the Raptors just happened to lose less than Miami did four out of seven times.

Toronto won Game 2 despite a 16-of-46 combined shooting effort from DeRozan and Lowry.

They were 6-of-28 in the Game 4 loss, just narrowly outgunned by Goran Dragic and ISO Joe, who went a blistering 10-of-29.

Miami evened the series at two despite going a cool 1-of-15 from three. Amar’e Stoudamire started that game in place of the injured Whiteside.

The tapes of this series should be put on display in a cold cellar in the hall-of-fame.

#30. 2016 — Round 1, Game 4 — TOR 83, IND 100 / Never Easy. Not Ever!

I never really thought DeMar and Kyle — especially Kyle — deserved quite as much scorn for their playoff maladies as they received. But uh... it’s a little more understandable when you flip from 2016 box score to 2016 box score in succession.

The pair followed up a couple nice, tone-reestablishing wins by scoring a combined 20 points on 8-of-29, including a donut on seven tries from deep. Ian Mahinmi and his week-old celery knees put up 22-10-5 on his own. A heinous game all around — and we only just hit the top-30!

#29. 2018 — Round 1, Game 4 — TOR 98, WSH 106 / Couldn’t Put ‘Em Away In Five, Huh?

Man, how are you gonna go and give up a 40-burger to the Wizards in the third quarter and call yourself different?

#28. 2016 — Round 2, Game 6 — TOR 91, MIA 103 / Of Course It’s Going Seven, You Fools

If anyone ever tries to tell you that game-to-game momentum in sports is a thing, slap them and remind them of the Raptors’ run to the conference finals. I remember feeling really confident in the Raps chances of closing out Miami in six. Game 5 was as resounding a win as you could have possibly hoped for in such a close (bad) series. To reiterate, Amar’e Stoudamire was starting for the Heat.

That experiment ended in Game 6. Justise Winslow became a full-time small-ball centre, and it flummoxed the Raptors enough to force a seventh game. The real shame of this one was the wasted 36-point KLOE explosion.

#27. 2014 — Round 1, Game 3 — TOR 98, BKN 102 / The Near 15-point Comeback

At spot 27 we mercifully get a break from the cruel and unusual meat-grinder that was 2016, and go all the way back to the series where the disappointments were positively regular.

Game 3 against the Nets was just a couple possessions from being all the way up in the Unbridled Joy section. A 15-point fourth quarter deficit was almost turned around by DeRozan’s 30-point night, and a highly uncharacteristic 17-spot from Patrick Patterson. Naturally 2Pat missed a pair of free throws to tie with 19 seconds left, which really beefed up the anguish this puppy produced.

#26. 2016 — Round 1, Game 6 — TOR 83, IND 101 / They Will Never Do It The Easy Way, Ever

Oh? You were feeling revitalized and, dare I say, hopeful after the Raptors pulled out that Game 5 miracle against Indy? Well, how would you like a nice punch in the face to knock your mood down a peg or five?

Of course all of the terribly annoying mid-series losses during that 2016 run were ultimately harmless to the Raptors’ campaign for the conference finals. In a sadistic way, games like the one that forced an uncomfortably tense Game 7 vs the Pacers enriched the post-season experience that year. A Game 7 triumph offers so much more drama and excitement than a ho hum four or five-gamer. Right?! Plus, without all those extra home games we never would have gotten to see the full array of graffiti tees the probably fired design team had in the bag. It just wouldn’t have been the same without the angry beaver, or the even angrier spitball.

Anyway, that’s enough despair for one day. Come back tomorrow as we dive deep into The Shit — the 25-most ulcer-causing playoff games of the last five years. There will be tears. LeBron may make an appearance, too.