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The Anguish Index: Every post-2014 Raptors playoff game ranked — #25-1

Here it is: a definitive ranking of the top 25 most painful playoff games in the last five years of Raptors history. We had to live it once — so let’s re-live it again and just get it out of our system.

NBA: Playoffs-Cleveland Cavaliers at Toronto Raptors Tom Szczerbowski-USA TODAY Sports

Welcome back! If you thought yesterday’s trip through sordid Raptors playoff history was bleak, are you ever in for a treat today! Part one was supposed to be the happy half of this exercise.

Today on our countdown to the most gut-punching Raptors playoff game this decade, you’ll really get to stare the futility of sports fandom in the face. And then it will probably spit on you. Paul Pierce makes way more appearances than he deserves to. The Raptors’ record in the games soon-to-be addressed is a combined 5-20 — which is also the shooting line DeRozan and Lowry each flirted with in just about every single one. You’re not even gonna wanna watch Raptors-Magic Game 1 by the time you get to the bottom. No need to delay the torture any longer; let’s begin, shall we?

Low-ish Stakes / High-ish Blood Pressure

#25. 2016 — Round 3, Game 1 — TOR 84, CLE 115 / Meh, It’s All Gravy

#24. 2016 — Round 3, Game 2 — TOR 89, CLE 108 / Yup

Look, did it feel good to get slapped by the Cavs in the opening game of the Eastern Conference Finals? No, not especially. But I’d posit the high of the Game 7 win over Miami had yet to wear off by the time Game 1 against Cleveland got going; the munchies snack of choice for Raps fans was a big vat of gravy. Life free of expectation rules.

Game 2 stung a little more, yeah. But even then, no sane person had the Raps winning that series against the eventual champs. Going down 0-2 was entirely to be expected. That the Raps hung around for an entire first quarter before the Cavs bench caved in their skulls was enough to satiate the thirst for legitimacy. What I’m saying is, be happy the 19-point, series win probability-zapping blowout loss wasn’t worse.

#23. 2014 — Round 1, Game 6 — TOR 83, BKN 97 / The Game Where They Just Couldn’t Seal It

You really couldn’t have felt too badly after Game 6 in Brooklyn. Yes, it was a missed closeout opportunity, but if those raggedy ass Nets had one thing going for them, it was experience. Had they fallen in six games the Pierce-Garnett trade would have really gone down as a failure!

Even after the loss, the Raptors had a rabid crowd waiting back home and probably could have been considered slight favourites to win Game 7. What could have possibly gone wrong.

#22. 2014 — Round 1, Game 1 — BKN 94, TOR 87 / The Buzzkill

This game had SO much build-up. Five seasons of playoff-less, Bargsariffic sludge, a front office change, the post Rudy Gay trade run, Jason Kidd spilling his drink like a punk, the Nets tanking down to the sixth seed, the first camera pans across the great Jurassic Park expanse, and then... wait... hold up... is that Drake narrating?!

Anything but a resounding Game 1 win was going to be a tremendous letdown after all that tantalizing foreplay. Joe Johnson and his 24 points on 8-of-13 delayed Toronto’s city-wide release in the most boring possible fashion.

Though in fairness, the first Raps playoff win since 2008 probably wouldn’t have felt as good as it should have had it been capped by Herbie Kuhn yelling “HORN!”

#21. 2016 — Round 3, Game 5 — TOR 78, CLE 116 / Ah Well It Was Fun While It Lasted

No matter what, Raps fans will always have “two wins away from the Finals.” They’ll also always have the therapeutic podcast our pals Blake Murphy and Alex Wong recorded for Raptors Republic in the wee hours following the Game 5 shellacking that put the Raps back in their place.

Recovery is a team sport.

Ulcer-Inducing Wins

Sometimes wins are terrible, too!

#20. 2014 — Round 1, Game 5 — BKN 113, TOR 115 / The ‘They Might Do This’ Game

The finish to this game was absolutely absurd.

Jonas Valanciunas is a huggable guy as it is. But have you ever wanted to hold and comfort someone as much as JV when it looked like he maybe committed history’s worst goaltend? This finish had everything, man, And when the review wrapped and Toronto emerged with a 3-2 series lead, you would have been forgiven for envisioning a series win and second round date with the Heat. Surviving that finish made it feel like the Raptors were destined for something other than supreme pain. Alas.

#19. 2016 — Round 3, Game 4 — CLE 99, TOR 105 / The Game Where They Were On Par

There was a malice to the way the Cavs carved up the Raptors in the fourth quarter of Game 4 in 2016. They scored on a dozen straight possessions, running the exact same option play that Toronto was hopeless to contain. Game 4 was not a throwaway hangover recovery day for the Cavs — that was Game 3. No, they threw everything they had at the Raptors as they sought to avoid a 2-2 split. LeBron played 46 minutes, putting up 29-9-6 on 11-of-16 from the floor. He initiated everything in the final 12 minutes, letting his gravity guide his playmaking. It was clinical. It was excruciating.

And it wasn’t enough.

DeRozan and Lowry were bosses, together — 67 points on a combined 43 attempts. It was the lone 48-minute instance over 14 meetings with Cleveland where DeMar and Kyle were on par with their tormentors.

And had the game been two or three minutes longer, it probably would have been a bottom-five loss on this list.

#18. 2017 — Round 1, Game 6 — TOR 92, MIL 89 / The One Where They Almost Blew It

The deciding Game of the 2017 first round, in which the Raptors nearly pissed away a 25-point third quarter lead in about the time Giannis takes to run a length of the court, would have ranked lot higher (lower?) if not for a few key factors. (1) Toronto had a bit of security blanket in the form of a Game 7 at home to bail them out. (2) The Raps played some truly inspired basketball for the vast majority of the game, which can not be said for literally any of the 17 games still to come. And (3) Crunch time produced a trio of indelible post-season moments: the only dunk of Patrick Patterson’s career, Cory Joseph’s three to take back the lead for Toronto, and DeRozan’s dunk on/over three fifths of the Bucks lineup:

Little did we know those were the last blissful moments of the 2017 campaign.

Pour the Pepto

#17. 2018 — Round 2, Game 4 — TOR 93, CLE 128 / The End

I was as despondent watching this game as the Raptors were playing it. With all that happened in the lead-up to this one — don’t worry, we’ll get there — how could anyone have expected the squad to have any sort of life. So many indignities suffered, so little wherewithal to do a damn thing about them. Lowry had his worst game of an otherwise Actually Good post-season. Ol’ Dwaner’s last piece of uncooked pasta to toss at the wall was late second-quarter Bebe. Poor guy went -10 in 1:51 and did not stand a chance.

The worst development of all? DeMar DeRozan — the face of the franchise for nearly a decade and holder of like every team record — got ejected in his last game in a Raptors uniform.

#16. 2018 — Round 2, Game 2 — CLE 128, TOR 110 / It’s Been Over Since Game 1

Ah, the “LeBron hits a thousand impossible shots in the third quarter cause he likes to be a meanie” game. With all the good Toronto for the first 47 minutes and 52 seconds of Game 1, and with all of the data still pointing to the 2018 Raps being among the best LeBron opponents since 2010, there was at least a faint outline of a blueprint for the Raps to follow en route to a long series.

That disappeared entirely when Dwane Casey used the phrase “play for pride” when asked about the way forward in Game 3.

That was a defeated man, speaking to an even more defeated fan base. We’re not even close to being done with that series, either.

#15. 2017 — Round 1, Game 3 — TOR 77, MIL 104 / Perhaps It’s Time to Panic


#14. 2016 — Round 2, Game 1 — MIA 102, TOR 96 / The Buzzer Beater No One Cares About

Even the nice and cool things that happened to the We The North era Raps did not always portend prosperity. Kyle Lowry’s half-court heave to send Game 1 of the Hell Series to OT was fucking insanity.

Look at the dejection on Wade’s face. Lowry’s grin is cheekier than his backside. And none of it mattered, because the Raptors couldn’t buy a bucket until the 1:24 mark of the extra period, putting to waste the miracle heave as well as a dominant 24 and 14 from Jonas Valanciunas, who was just a six quarters away from being excised from the remainder of the series. All this game amounted to was a late bedtime. It gave us Lowry’s late-night emo shooting session, too.

#13. 2017 — Round 1, Game 1 — MIL 97, TOR 83 / This Shit Again?

#12. 2016 — Round 1, Game 1 — IND 100, TOR 90 / This Shit Again?

Game 1 losses, at home, as clear favourites. It’s The Raptor Way, baby.

Catastrophic Intestinal Damage-Causing Wins

#11. 2016 — Round 1, Game 7 — IND 84, TOR 89 / The Exhale Game

It’s impossible to overstate how much the future of the franchise hinged on the outcome of Game 7 against Indy. A loss to Paul George and his bum ass pals would have probably cost Casey his job. Letting DeMar walk, dealing Lowry and nuking the whole damn thing would have been on the table, one would think.

For three quarters it seemed like the Raps were gonna do the thing — power through the pressure, dispatch their inferior, and win a series for the first time since 2001. With how junky Indy’s offense was, a 78-64 lead through 36 minutes seemed screw up-proof. And I mean, seeing as the Raps won despite scoring just 11 points in the quarter to Indy’s 20, I suppose it technically was.

#10. 2016 — Round 1, Game 5 — IND 99, TOR 102 / Thank You Frank Vogel

All the heavy contextual elements of Game 7 against Indy applied to Game 5 as well, except Game 5 didn’t see the Raptors hold a nice lead for, uhm, any amount of time at all. Rather, it was the Raptors who had to make up a 13-point deficit — a hole they absolutely deserved to be in. Lo and behold, they made it happen, orchestrating a 25-9 fourth quarter dissection of the Pacers — aided, of course, by Frank Vogel rolling out his incomprehensibly bad, Ty Lawson-led second unit for a good five minutes to start the frame. Norm dunked. Drake may or may not have scared Rodney Stuckey into a turnover? Both of those clips are too cheerful to plop into this joy-free space I’m trying to cultivate. I will, however, include Solomon Hill’s almost game-tying three at the end of regulation.

That review process was hell. An overtime in which Paul George actually played and Lawson almost assuredly would have not was not something anyone in the building was going to feel good about.

Speaking of things no one feels good about ... I guess we should address the Wizards...

That Sweep You Probably Repressed

#9. 2015 — Round 1, Game 4 — TOR 94, WSH 125 / The Resigned-to-Death Game

#8. 2015 — Round 1, Game 1 — WSH 93, TOR 86 (OT) / The Shimmy Game

#7. 2015 — Round 1, Game 3 - TOR 99, WSH 106 / The It’s Over Game

#6. 2015 — Round 1, Game 2 — WSH 117, TOR 106 / James Johnson Was Not The Answer

When I first put out the call for people to share with me their selections for the most agonizing Raps playoff Ls, one of the most common responses was “All of the Wizards Games.” Those folks were on to something! What a ghastly week of something vaguely resembling basketball. It feel right to lump them all into their own miserable category.

Landing on a proper order, though, is tricky. Each of these four nightmares had a unique brand of stink.

After a pair of sweeps at the hands of Cleveland, Game 4 almost feels like a familiar old pal. A wire-to-wire shit-canning where the outcome is preordained and you can allow the sports depression to consume you? Hell, that’s most Raps playoff losses. I for one welcomed the sweet release of elimination after the three games that came before.

Game 1s are a touchy subject in these parts, but OT loss to the Wizards wasn’t as deflating as some other series opening duds have been. That’s not to say it was good. Dwane Casey started Tyler Hansbrough because Amir Johnson was apparently just not psycho enough. Toronto scored 33 points over the course of quarters two and three. Lowry, DeMar and Lou Williams combined to go 12-of-46. Worse Than Dwyane Wade scored 20 points on 10 shots just days after that whole “It” business.

The Greivis Shimmy is really the only thing keeping this from being the worst of the Wiz games.

Game 3 arrived with a faint sense of optimism that maybe it wasn’t totally over. It’s not like the Wizards were all that impressive through two games — the Raps just wet themselves oh so amply. All they had to do was keep their trousers dry and baby it’s a series! DeMar even felt good before the game!

More like Fuck it, Let’s Get Hit, amirite.

Kyle proceeded to shoot 5-of-22. Lou was balmy by this series’ standards with his seven points on eleven shots. And of course, there was Paul Pierce...

I wasn’t gonna put that video in the post. It felt almost too mean, and Pierce’s thirsty ass deserves less than zero shine. But if I had to relive it you’re all gonna too.

And lastly, we come to Game 2. Personally, I find it to be the most loathsome game the Raptors have ever contested. Part of my hostile feelings here stem from the $150 I spent for not very good upper bowl seats. It was also the game where Lou Williams received his Sixth Man of the Year Award, underscoring one of the most severe symptoms of that team’s post-season unsustainability. And then there was the standing ovation for accused domestic abuser James Johnson, who for some reason was seen as the answer to the Wizards’ Raptor-killing small-ball lineups in some fan circles, in spite of the fact that he was bad at defense. Pierce drilled a three in Johnson’s eye seconds after he entered the game. If I were more honest with myself at the time, I would have recognized that game as the thing it was: the fucking end.

The Deepest Pits of Despair

#5. 2014 — Round 1, Game 7 — BKN 104, TOR 103 / The End of the Magic

This was a surprisingly tricky game to place. With the benefit of five years of distance, this game mostly sparks warm feelings in my otherwise disappointment-hardened gut. It was a game that promised a brighter future than anyone could have dreamed up five months prior. Amir’s 20 and 10 on those Crunchie bar ankles is a touchstone Raps playoff performance. ESPN was there. Jurassic Park was at its absolute rockingest. Terrence Ross’s steal and throw off Paul Pierce’s aged shins is my favourite NBA play of all time, and it should be yours too!

But a game ending with a happy Pierce, a crestfallen Lowry, and a series loss had to be in the top-five. Find a loved one’s hand to hold, and press play.

#4. 2017 — Round 2, Game 2 — TOR 103, CLE 125 / Kyle Gets Hurt, End of the Era??

Nothing quite like following up the most complete humiliation the franchise has suffered since Araujo with a blowout ass-whooping in which your best player — who happens to be a free-agent seemingly teetering on the verge of bolting — screws up his ankle and ends his season.

#3. 2017 — Round 2, Game 1 — TOR 105, CLE 116 / The Game Where LeBron Played with his Food

Two minutes and forty-eight seconds. It’s the ideal length of a good punk anthem. It’s about how long it takes to nuke a bag of popcorn. It’s the record for the fastest clinching of a series victory in NBA history.

Those were certainly the loudest of the 35 points LeBron put up in the round two opener that year. The rest of his buckets came so easily that he kicked back and pretended to drink a damn beer in the middle of the game. P.J. Tucker was supposed to, at long last, give the Raptors a legit LeBron foil. Instead, he gave us this.

Via u/clumsynincompoop on Reddit

This game was like watching your own colonoscopy with surround sound.

#2. 2018 — Round 2, Game 3 — TOR 103, CLE 105 / The Buzzer Beater

This is... probably the Raps playoff game with the wildest swings of emotion ever, yes? At halftime Toronto trailed 55-40, which seemed insurmountable. Hell, leading a LeBron team by 15 sometimes felt like a deficit. Personally, I was feeling glum enough about the whole thing that as the second half began, and my blood alcohol rose, I started blending Wilco lyrics with notes of Raptors heartbreak in what remains one of my worst uses of the internet.

But as the album turned over to side two, Dwane Casey decided to like, actually do some in-game coaching, and ran out an Ibaka-Siakam front-court flanked by OG, Fred and Lowry. It was that group that powered a rousing, belief-restoring comeback. OG capped it off by brandishing his nuts and canning the game-tying three.

And then the most incredible thing happened! The referees stopped the game with 8 seconds left, and awarded both teams a tie. And then we all went to bed happy and I did not drink alone until 2am. I told you. An emotional roller coaster, that game was.

#1. 2018 — Round 2, Game 1 — CLE 113, TOR 112 (OT) / The Missed Tip-in Game

The 2018-19 Raptors were different. The bench was going to sustain in the post-season. The offense was trap-proof as it had ever been. The Cavs were a disaster that swapped one heaping shit pile of a roster out for another at the deadline. Toronto’s advanced metrics, hoo baby those were sweet. Cleveland’s defense was better than only that of the Sacramento Kings! LeBron’s old sidekick? Gone, cause he hated it there. Psychological obstacles — schmycholigcal schmobstacles. This was the series; this was where the dragon would be slain, where LeBron’s vice-grip around the neck of the easternmost half of a continent would be pried apart. The Raptors were finally gonna do the damn thing. Even smart analysis types agreed!

And then this inexplicable bullshit happened.

For years, I had been very much opposed to diagnosing the Lowry/DeRozan/Casey Raptors as mentally fragile. It felt a little icky, and also kind of undersold how freaking great those LeBron/Kyrie Cavs teams were. Game 1 last year was the point at which I gave in to the idea of some funky shit going on the Raps’ heads in the face of Cleveland. The fact that Dwane Casey made reference to some sort of “Game 1 hangover” after each of three subsequent Ls kind of proved something bigger than the on-court play was going on.

Maybe it wasn’t all bad, though? The loss pierced the aortas of an entire country in the moment, yeah. But maybe this game was the last straw for Masai Ujiri — the inciting incident for the off-season makeover than landed the guy who could be the antidote to all the hypertension and fear.

This year actually will be different. It should actually be enjoyable, even... fun?! The heartbreaks of 2014-18 are in the past, and Toronto’s storybook’s been flipped to a crisp new page.