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Why do the Basketball Gods continually taunt the insecure Raptors fanbase?

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By getting the Orlando Magic, the Raptors have once again, drawn the worst first-round opponent possible. We dive deeper into their post-season history of nightmares (yay!)

NBA: Playoffs-Toronto Raptors at Cleveland Cavaliers Ken Blaze-USA TODAY Sports

Because we’re Raptors fans, and masochists, and we secretly expect the sky to fall down on our heads. I bring you this:

So, confession. I’ve never actually seen this play before. I originally followed this game on my phone on the TTC. I was coming back from the airport, and it was killing me that I wasn’t going to be able to watch Game 7.

I remember realizing the Raptors had the ball down one with seconds left, when woosh — into a tunnel. When I came out, I refreshed my phone over and over, until, FINAL SCORE: BKN 104 - TOR 103. The final play — BKN: P. Pierce BLOCKS K. Lowry’s lay-up attempt.

In my mind I just decided that it was some heroic, ridiculous, very Raptors-esque effort from Pierce to end it all. I didn’t need to watch the highlights. I just didn’t, you know? And then I never thought to dig it up afterwards, I mean, what’s the point of revisiting that old wound? (Yes, I may take this stuff too seriously.)

In the end I decided that this was the best way for me to consume Raptors playoff games. Dispassionate text. Paul Pierce hits a three? He does that. DeRozan misses a six-footer? I can assume it was a good shot that rimmed out. I don’t need to know that Pierce’s came after three deflections sent the ball rolling to him, wide-open, behind the arc. I’m better off not knowing that DeMar had dribbled the air out of the ball for 13 seconds before launching a triple-teamed fadeaway.

Part of this is because I’m a wimp. I’m the guy who reads Wikipedia entries, and then sees the horror movie. Because even knowing when the scares are going to happen, doesn’t keep me from being scared — it just makes it bearable.

But there’s an even more specific reason I need text. It’s because the Raptors’ first round playoff match-ups always feel like a horror film. Whenever there is a chance for Toronto to end up with serial killer lurking behind the smile, they do.

One thing that made the Nets series of 2014 so painful was that it wasn’t until the last day that the Raps knew their opponent, and of course, out of all the options, it was the one that scared the bejeezus out of me.

So, without further ado, let’s take a tour of what I like to call: The Why Do The Basketball Gods Love Taunting The Incredibly Insecure Raptors Fan Base With The Worst First Round Match-ups Possible Hall of Fame (or WDTBGLTTIIRFBWTWFRMP Hall of Fame for short).

2006-07

The Match-Up: (3) Raptors vs. (6) New Jersey Nets

The Team: The first of the heart-breakers. The Raptors out-of-nowhere season where a collection of kids (Andrea Bargnani was a rookie, and Bill Simmons was swooning, T.J. Ford, Joey Graham), Euro-league imports (Jose Calderon, Jorge Garbajosa, Anthony Parker), and one star (Chris Bosh) figured out how to play with each other at mid-season, going 24-12 down the stretch to win the Atlantic.

The Achilles Heel: As mentioned this was a young team. Morris Peterson was the elder statesman (who played), and he was in year six with no playoff experience. And while Garbajosa, Calderon, and Parker brought a wealth of international experience they’d never played in the cauldron of the NBA post-season.

The Standings: NJ 41-41, Washington 41-41, Orlando 40-42

Why I Didn’t Want Who We Got: I think we forget how legitimately good this Raptors team had become. Their Achilles heel meant the one thing they needed was playoff experience. Has they got a less-seasoned first round opponent, I think they would have had growing pains, but Toronto ultimately would have prevailed.

Once they got through Round 1, I truly think they could have made a run to the Eastern Finals (nobody was beating the Pistons that year). That could have changed everything — the league’s perception, the way they handled the Garbajosa injury (after a Conference Finals run, why not be patient?), and more. With a playoff series win, or two, would Bryan Colangelo let things grow organically, rather than flying into the Jermaine O’Neal move that started their quick descent? A huge Sliding Doors moment for the franchise.

How the Basketball Gods &%^$& us: New Jersey had been to the playoffs six consecutive years, and still had two key members, Richard Jefferson and Jason Kidd, from the team that had gone to back-to-back Finals. They had sleepwalked through the season, before finishing on a 10-3 run. (They were also 7-1 in games decided in OT or by five points and less.) This was the definition of a veteran team that knew how to win, peaking at the right time.

In contrast, Washington went into the playoffs on a 4-14 slide. Orlando was 6-1 down the stretch, but faced some weak opponents. They were just 10-10 in their last 20.

So, yeah. I’d say the Raps definitely got the short end of the stick here.

2009-10

The Match-up: None

The Team: The Raptors last gasp with Chris Bosh ended with a whimper, as the Raps collapsed down the stretch to allow the Chicago Bulls to pull past them by a game. Toronto had the tie-breaker too.

Why This Is Here: It probably didn’t matter. Even if Toronto had made the playoffs, LeBron would have eviscerated them with one of his few, truly great, Cavaliers teams. If anything it would have made switching jerseys even more appealing to Bosh. Still, maybe a playoff run could have kept Bosh around.

Also, I wanted to include this...

If this rims in, Toronto goes to the post-season for a third time in four years. Bosh probably still does leave, but again, the narrative around the franchise might have changed. As we’ve learned in the last few years, culture matters.

(Plus, how is the music not the theme from Titanic? I mean you’re almost all the way there, wsupbrandon. Finish the job. FINISH THE JOB!!!)

2013-14

The Matchup: (3) Raptors vs. (6) Brooklyn Nets

The Team: The first-year of the current Rapto-ssance was as magical as it was unexpected. Toronto famously came this close to blowing it all up, until James Nolan got scared of being pantsed by Masai Ujiri, again.

After a 6-12 start, Toronto went 42-22 the rest of the way to win the Atlantic crown. We got the budding bro-mance of Kyle Lowry and DeMar DeRozan, the NBA introductions of Jonas Valanciunas and Terrance Ross, and the irrational confidence of Greivis Vasquez.

The Achilles Heel: Well, this team was woefully short of playoff experience. Aside from Vasquez, John Salmons, and Kyle Lowry’s brief-run as a Houston Rocket, none of the Raptors key contributors had played in the post-season. But they were really good and had gelled. As long as they didn’t run into a team with an inordinate amount of playoff experience they should be fine. Right?

The Standings: Toronto 48-34, Chicago 48-34, Wizards 44-38, Nets 44-38, Bobcats 43-39

Why I Didn’t Want Who We Got: Is that the Nets $%&*ing music!!! The same Nets who just happen to have Paul Pierce, Kevin Garnett, Joe Johnson, Jason Terry and their approximately 23,987 playoff games of playoff experience?! (All number approximate.)

How the Basketball Gods &%^$& us: Perhaps you missed the “Paul Pierce, Kevin Garnett, Joe Johnson, Jason Terry and their approximately 23,987 games of playoff experience?! (All numbers approximate)” part? Also, with eight games left the Nets were sitting in 4th spot, but they went 1-4 down the stretch to “accidentally” fall into the 6th spot.

Now, to be fair, the Wizards had a handful of vets (Trevor Ariza, Nene, the Professor Andre Miller) went 6-2 down the stretch and actually beat the Bulls — but that was John Wall and Bradley Beal’s first post-season, and the Bulls had lost Derrick Rose.

The Hornets were hot too, 19-9 to finish, 7-1 down the stretch, but their entire young core (Kemba Walker, Gerald Henderson, Kidd-Gilchrest, Cody Zeller, Josh McRoberts), had never played in the post-season. And the Hornets vets (Ben Gordon, Al Jefferson, Ramon Sessions) aren’t nearly as threatening as KG and PAUL F—ING PIERCE!

2014-15

The Matchup: (4) Raptors vs. (5) Washington Wizards

The Team: In retrospect, it may not have mattered who the Raps faced, as this was the franchise’s premier gut-punch edition. After a blistering 24-7 start that had people legit talking about a Finals appearance, the Raps swooned to a 25-26 finish.

The Achilles Heel: The core was effectively the same (Lowry, DeRozan, Valanciunas, Patterson, Amir Johnson, Greivis, Ross), and the Raps even had the 6th Man Of The Year in Lou Williams, but for whatever reason — cough, cough, iso scoring, cough, cough, no perimeter defense — it all fell apart.

The Standings: Bulls 50-32, Raptors 49-33, Wizards 43-36, Milwaukee 41-42, Boston 40-42

Why I Didn’t Want Who We Got: The Wizards were obviously better than the Bucks and the Celtics. They had gained confidence by beating the Bulls the year before, and legitimately believed they were good enough to beat LeBron (they were deluded, but still).

In contrast, the Raptors were operating with zero confidence.

How the Basketball Gods &%^$& us: Well, almost zero confidence. Toronto actually finished a respectable 7-3 down the stretch, with all three losses coming by five points or less. Chicago did the same. The problem was that 11th to last game: the Bulls beat Toronto 116-103 on the second night of a back-to-back and the third of a “three in four nights” stretch.

It was the schedule makers fault! If Toronto played the Bucks (Giannis’ rookie year, Brandon Knight was their leading scorer), they could have won and got their swag back! Or the Celtics, who, uh, [checks notes], had Rajon Rondo, Marcus Smart, Jae Crowder, Jeff Green, Evan Turney and Avery Bradley and went 17-7 down the stretch...

OK, never mind... we were pooched.

2015-16

The Matchup: (2) Raptors vs. (7) Indiana Pacers

The Team: The core was the same, but everyone was a year more experienced, and the Raps got a badly needed dose of energy from Bismack Biyombo who, despite, or maybe because he had anvils for hands, wasn’t afraid of anyone. Not even LeBron.

I will go to my grave knowing this was not a foul:

The Raps also had Cory Joseph, a gritty vet who’d been to the Finals with the Spurs; DeMarre Carroll, who was a bit of a bust on the court, but also had some vet sheen; and a precocious young second-rounder named Norman Powell.

The Achilles Heel: Confidence. Just a little bit? That, and the fact that people were starting to realize that a six-foot point guard, and a shooting guard who wasn’t great at shooting might be stoppable.

All, unfair DeMar shade aside, he was great this year, it was just clear that big athletic wings with savvy defensive instincts could slow DeRozan and pull the Raptors’ offense down with him. There was also the growing fear that the Raps’ superior depth might not mean much, and they were going to be vulnerable to teams that had the best player in the series.

The Standings: Cleveland 57-25, Raptors 56-26, Pacers 45-37, Pistons 44-38

Why I Didn’t Want Who We Got: Remember that Achilles heel? Yeah, well Paul George was created in a lab to exploit that.

How the Basketball Gods &%^$& us: It may seem strange to curse the Gods in what was the most successful season in Raptors history, but Toronto was this close to losing that first round series. Surely that would have meant a massive tear-down. No DeMar, no Kyle. (Which also means no Kawhi.)

Would the Raps have flipped the pick that became Pascal Siakam to clear Carroll’s contract a year early (likely having one or two earlier picks from Kyle and Demar deals)? It’s another massive Sliding Doors moment.

Remember too that the Cavs faltered down the stretch, going a pedestrian 8-6, which opened the door for Toronto to get the one-seed. Meanwhile, the Pacers stormed into the playoffs on a 6-1 streak, passing the Pistons, who had a little Andre Drummond,-Reggie Jackson pick-and-roll magic happening, but not much else.

If Toronto gets Detroit, they probably destroy them. Maybe that ends the “deep down we’re all a little terrified the Raps will crap the bed against an inferior team” feeling that still grips the city today (and is the reason these 3,000 words even exist).

2016-17

The Matchup: (3) Raptors vs. (6) Milwaukee Bucks

The Team: The core was the same, but this was the first of the “Kyle Lowry can’t stay healthy because secretly he’s getting kinda old for a lead guard” years (he played 60 games). The Raps thought Jared Sullinger was the answer at the four, but he got hurt and so way-too-raw rookie Siakam started half a season. Toronto swung a big deal to get Serge Ibaka, and a smaller one for P.J. Tucker, signs that Masai Ujiri understood the Raptors needed some swag in the room.

The Achilles Heel: Still the same path to victory. When Ibaka scuffled as a Raptor, the dream of a Big 3 died. And, with the rest of the names remaining the same (Valanciunas, Carroll, Patrick Patterson, Joseph), there was a feeling that Toronto had proven that it’s formula of DeMar and Kyle couldn’t work.

The Standings: Cleveland 51-31, Toronto 51-31, Atlanta 43-39, Milwaukee 42-40, Indiana 42-40, Chicago 41-41, Miami 41-41

Why I Didn’t Want Who We Got: Giannis had just submitted his first “one name” season, and like the year before, the concern was that a hard-nosed team, led by a physically superior superstar who was better than anyone Toronto had, could turn the tide.

How the Basketball Gods &%^$& us: The Raps actually were great going into the post-season, 12-2 in their last 14, but the Cavaliers again teased us with a late-season fade (6-8), that fell just shy of granting Toronto an easier foe.

The Bucks went wild down the stretch, going 16-7 to secure the sixth seed. Behind Toronto, and one other team, they were the second hottest team in the East heading into the dance.

Meanwhile, Atlanta went 11-16, but 4-1 in their last five to just hold off Giannis. The Hawks were only two years removed from their 60-win team, but the tear-down was almost finished — only Paul Millsap remained from that core.

Indiana went 5-0 down the stretch to get into the playoffs, but they were 7-17 in the 24 games before that, and there was a sense that Paul George had checked out.

The Bulls were a ho-hum team who were 10-10 in their last 20 and had a roster of blah.

Meanwhile, the Heat missing the playoffs seems like evidence that the Gods don’t completely hate the Raptors. But instead, Miami went a bat-shit crazy 30-11 in the second half. They didn’t make the playoffs, but there’s a universe out there where they squeeze into seventh and upset the Cavs in the first round — which would have spared us all those LeBronto memes.

Which brings us to...

2018-19

(I’m skipping last year, despite all the whining about the Wizards top-end talent being the worst match-up, because, while the Wiz did lose their way into the match-up, a la the Nets in 2013-14, neither the Heat or Milwaukee stormed past them. And deep down Raps fans were secretly OK with it. We knew how dysfunctional that team was.)

The Matchup: (2) Raptors vs. (7) Orlando Magic

The Team: After fighting through the early season deluge of non-stop: “Kawhi wants to play for the Clippers” pieces (I mean even BUSINESS INSIDER wrote one of the damn things), the Raptors have had a pretty boring season. Sure there have been injuries, odd stretches of dispirited play, the super-nova emergence of Pascal Siakam, the up, and down, then back up season of Serge Ibaka, and the “did that trade make us better or just different?” Marc Gasol deal, but overall it’s been very... business like.

Achilles Heel: Is there one? I mean, for awhile it looked like it was Kyle Lowry being washed. Then it seemed it was the teams inability to hit a three-point shot. And, of course, there’s been a lot of hullabaloo about the bench (which, for the record, doesn’t suck, it’s just no longer clear and away the best bench in basketball), but overall this is a team with a lot more strengths than weaknesses.

But, if you were going to pick something: facing a team that has a bully-ball centre, long-armed defenders everywhere, and a spindly four who could keep Pascal Siakam in check wouldn’t be good. Especially if they had beaten the Raps a couple of times and were playing really good basketball.

Oh. Shit.

Standings: Brooklyn 42-40, Orlando 42-40, Detroit 41-41

Why I Didn’t Want Who We Got: Let’s get this out of the way. Nobody should be scared of Detroit. Yes, they went 3-0 against the Raps, but it was by a total of 10 points. Blake Griffin is hobbling around, their wings are all one-dimensional, and they were a thoroughly mediocre 11-10 in their last 21.

The Nets bring a guy who can take over quarters in D’Angelo Russell, a great pick-and-roll attack, and the danger of four hot three-point shooting nights, but they can’t guard Leonard, Lowry or Siakam.

The Magic though... they’re better than you think. They’re 21-9 in their past 30 — the second best record in the East behind Milwaukee in that time. They’ve also been the league’s best defensive team since February 1st. They have been up by at least 18 points in three of their four games against the Raptors, and they have the length, and bully-ball centre (Nikola Vucevic) needed to attack the Raptors lack of rebounding, and to make Kawhi and Siakam uncomfortable.

How the Basketball Gods &%^$& us: Well, I mean you never like playing a team whose been playing .700 ball for over two months, especially when they clinch going against you on the last day of the season. That feels... unlucky.

Still, the last game saw the fully operational Raptors, with the bulky Marc Gasol at centre, handily beat the Magic. So, it’s not like Toronto fans should be scared, but of all the possible first round opponents Toronto could have got, they received, easily, the worst.

Because of course they did. Because the Basketball Gods still don’t want me to ever feel comfortable actually watching a playoff basketball game.