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Most heartwrenching D.C. sports losses of the decade

We're a bit late to the Top 10 decade retrospectives, but we'll be ramping things up in the next few days, with a few local and national lists. In the meantime, I was wondering in the shower this morning where the Cowboys/Eagles/Saints triple-play of anguish would rank in a list of this decade's most gruesome D.C. sports defeats.

Of course, a decade is a long time, and this one seemed to last several centuries, so it turns out these most recent vomit-inducers aren't even close to qualifying for Top 10 status. So many to choose from. Ah well, here goes.

(And yes, this list is slanted toward the end of the decade. Because at the end of the decade I was writing about sports, and at the beginning of the decade I was selling cheese. So sue me. Also, no wheel of Parmigiano-Reggiano has ever broken anyone's heart.)

(And also, the decade will end with the Caps having gone 1-5 in playoff series, the Wizards having gone 1-4 in playoff series, and the Redskins having gone 2-3 in the playoffs.)

10. Raptors 2, Not Possible 0, 2007-2008: Let's start this off with some regular season madness. Probably this doesn't deserve to be here, but it led to one of the greatest broadcasting moments of the decade, so we'll make an exception. The agony started on March 30, 2007, when, in an attempt to polish off the clock, Michael Ruffin...well, let me let Ivan Carter take over:

There are shockers and then there is seeing Michael Ruffin, game and third place in the East in hand, attempt to loft a ball up in the air and kill the clock only to have it slip out and wind up in the hands of Morris Peterson, who then threw in (I swear he didn't shoot it; it was more like a loft) a threeball from 31 feet away, tying the game, forcing overtime and all but ripping the heart out of the Wizards and their fans. Unreal.

The rematch with the Raptors the following year didn't have quite as much at stake, but the Wizards still had the game completely and totally won. And then, magic:

(You'll note below that there are many more worthy candidates, but damn, that audio is good.)

9. Duke 95, Maryland 84, March 31, 2001: Having had their hearts crushed by Duke just more than two months previously (see below), the Terps met the Devils again in the Final Four, and improbably seized a 22-point lead, 39-17. Maryland still led by 11 at halftime. And then, blech.

"One of the most bitter defeats in [Maryland] history," Thomas Boswell wrote.

8. Seahawks 35, Redskins 14, Jan. 5, 2008 The final score is entirely misleading, because well into the fourth quarter, fans were convinced this team was headed for the NFC championship game. Remember, Washington--behind Todd Collins--had gone on that remarkable late-season four-game winning streak to make the playoffs. A win here, and they'd be off to Dallas, against the crumbling Cowboys whom they had just whipped, and who were dealing with Tony Romo's Cancun-gate.

They were down, 13-0, late in the third quarter, but then there was the touchdown drive, the LaRon Landry interception, the quick strike to Santana Moss, and the team of destiny was ahead, 14-13. The Seahawks botched the next kickoff and Washington had the ball at the Seattle 14. You couldn't have possibly convinced me they'd lose. But then suddenly the offense went away, Shaun Suisham missed from 30 yards, and it all fell apart, culminating with the two returned interceptions and the 21-point loss in Joe Gibbs's final game.

"There is no logic behind feeling cheated Saturday, but that pang is still there," Mike Wise wrote. "Every time a stirring, pixie-dust run like this ends abruptly, an emotional response follows from the aggrieved player or fan, who believe teams with heavy hearts should have divine endings, who deeply feel the Washington Redskins deserve to keep going, because it would somehow be right and fair."

7. Davidson 74, Georgetown 70, March 22, 2008:

The Hoyas were coming off a Final Four year. They were a second seed, with four high school All-Americans. They were up 17 in the second half. Roy Hibbert and Jonathan Wallace and Tyler Crawford, the seniors who had led Georgetown's resurgence, were ready for another trip to the Sweet 16.

Then Stephen Curry happened. After starting out 2-for-12 from the field, he scored 25 of his 30 points in the final 15 minutes. The comeback seemed to be over in about 20 seconds. The Hoyas are still waiting for their next NCAA tourney win.

Thomas Boswell, who has made a habit of witnessing heartbreak, wrote that it was Georgetown's "most shocking boot from March Madness in more than 20 years."

6. Lightning 2, Capitals 1 (3 OT), April 20, 2003: Mentioned far less often than the more recent defeats by heartsick Caps fans, but the details seem compelling. The Caps won the first two games of the series in Tampa, with Michael Nylander scoring two goals, one of which was a game-winner.

Then came four straight losses, three by a single goal, two in extra time, three at home. Both overtime goals came on power plays, with the first one the NHL's first overtime five-on-three goal in 70 years, and the final one a too-many-men-on-the-ice call against Jason Doig. "Heartbreaking but familiar," wrote Jason La Canfora in his gamer."

In this final game, the Caps led 1-0 late in the second period, but couldn't score again.

"Things just happen, I don't know why," Olie Kolzig said. "Why haven't the Red Sox won the World Series in how many years? For some reason every series there is something that we can't control that happens and seems to turn the series around for the opposition. Things just happen."

(I know you're all going to complain about me including this over the Flyers, but I just couldn't have it be so late-in-the-decade heavy. Still, feel free to let me have it.)

5. Buccaneers 14, Redskins 13, Jan. 15, 2000: Sure, you maybe didn't expect Norv to lead his team to the NFC championship game, but c'mon, this was bad. The Redskins were up 13 with 8 minutes left the third quarter. The Bucs were led by Shaun King, a rookie quarterback. The Super Bowl years were still fairly recent memories. The city was even warming up to Daniel Snyder: "Pleased by Success, Fans Decide Snyder May Not Be So Bad," read a WaPo headline this week.

The frittering was bad; early in the fourth quarter, Brad Johnson fumbled in his own territory, and on the ensuing possession, King was sacked and fumbled on third down but Warrick Dunn picked up the ball and ran it for a first down.

And even after the lead was fully frittered, there was a chance to win, with Brett Conway lining up for a 52-yard field goal. And then the snap got screwy, bouncing halfway to Conway; he said that would happen "one time out of probably 10,000."

"The steak was on the plate, it was all cut up, and then we can't eat it," Tre Johnson said.

4. Duke 98, Maryland 96 (OT), Jan. 27, 2001: The Terps played a brilliant game against their ultimate rivals, who were ranked second in the country, and led by 12 with 70 seconds left and by 10 with a minute left. The fans were chanting "overrated" and getting ready to storm the court. "They need a miracle," the TV guy said. His color man said a Terps loss would be "catastrophic." The miracle happened. There were no titles at steak, but for pure absurd, unforgettable agony, this one ranks.

"The whole team kind of just collapsed," Steve Blake told William Gildea.

"That's the worst loss that I've been associated with," Mike Mardesich added.

3. Penguins 6, Capitals 2, May 13, 2009: The exact opposite of the Caps loss below. Instead of a last-second heartbreaker, it was a nasty dose of anti-climax. The Cavs were just becoming the Wizards' rivals, but the Penguins had always been so. The Caps had the home ice, and seemed to have the fates on their side, until the fates decided to extract various livers and kidneys and other innards and just stomp on them. Things were brightened up by that late-game standing ovation, but only marginally. Instead of a celebration, fans had witnessed a disaster.

"I've never really seen anything like this and I've never been a part of anything like this," Brian Pothier said. "Every time we touched the puck, it seemed to explode. Every time they touched it, it was a goal. It was just crazy. You have these nights during the season, during the regular season, but I've never really experienced it in Game 7 of such an emotional playoff series."

"No way to describe it," Tom Poti added.

2. Cavaliers 114, Wizards 113 (OT), May 5, 2006. Yes, it was just the first round. And yes, it was just Game 6, and true heartbreak should always come in Game 7.

But consider the circumstances. The Wizards had already lost two games in this series by a single point. They had their best player on the free throw line in overtime with a chance to clinch things, but instead the loathsome Crab Dribbler whispered in his ear and he missed twice. Then Damon Jones, one of the least likable players on the planet, came off the bench ice cold. He played just 14 seconds in the game, but he hit the ultimate dagger, leading to the pile up on the Wizards' home court. And it led to a first-round knockout a year after the Wizards had been to the second round.

"To give away one, as precious as playoff games are, is demoralizing," Michael Wilbon wrote. "To give away three in one series is a sin."

1. Bills 17, Redskins 16, Dec. 2, 2007. Washington Post headline: "A Kick to the Gut." Sean Taylor had just died. People were emotionally wrecked. The weather was crummy. The Bills were using their third-string running back. Washington had the game won, 16-14, but couldn't run out the clock. The Bills--the awful Bills--got the ball back on their own 22 with less than a minute left. Somehow they wound up in field-goal position.

And then the legend, Joe Gibbs, the man who was keeping it together for everyone else called those consecutive timeouts, leading to the 15-yard penalty. As players got ready to fly to Taylor's funeral, they anonymously ripped Gibbs to the press.

Thomas Boswell said it might have been "the saddest game in Redskins history." "The Redskins ended the day with a 17-16 defeat as bitter to swallow in every respect as a mere game can be," he wrote. "Nobody said life had to be fair, but this is getting to be ridiculous."

Honorable mentions: Flyers 3, Caps 2 (April 22, 2008), Seahawks 20, Redskins 10 (Jan. 14, 2005), Florida 73, George Mason 58 (April 1, 2006), Buccaneers 36, Redskins 35 (Nov. 13, 2005), Eagles 23, Redskins 20 (Nov. 26, 2000), Penguins 3, Caps 3 (April 24, 2001), Rams 19, Redskins 17 (Oct. 12, 2008), Saints 33, Redskins 30 (Dec. 6, 2009).

(Photos by John McDonnell and Toni L. Sandys - TWP)

By Dan Steinberg  |  December 7, 2009; 12:53 PM ET
Categories:  Caps , College Basketball , Redskins , Terps , Wizards  
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Reading this list was depressing. Oy

Posted by: JDP_ | December 7, 2009 1:07 PM | Report abuse

And we wonder why people think DC is a bad sports city... it's cuz the local teams consistently give fans to be depressed!

Posted by: JMSinCHeights | December 7, 2009 1:09 PM | Report abuse

You're right. I'd actually put the Flyers OT loss and the Tampa Bay OT loss ahead of the Pissburgh loss. The Pissburgh loss was depressing but it was a foregone conclusion after the first few minutes of the games. The other two were tear your heart out hurtful.

Posted by: poguesmahone | December 7, 2009 1:15 PM | Report abuse

To me, the Pens loss is worse because it was so unexpected and if you add in the easy road the Pens had over the Canes to get to the finals, the pain of what might have been makes it even worse. Also, sitting in the stands while the Pens fans in front of us danced the night away wasn't exactly pleasant.

Posted by: amberlynne | December 7, 2009 1:17 PM | Report abuse

I'm sorry, the 2006 playoff loss to Seattle was far more heart-wrenching than the 2008 one. In '05, the 'Skins were actually good. In '07 they got lucky. Besides, it was after that January 2006 game that everything changed--Al Saunders came, Archuleta came, and it's been all downhill ever since.

For the Nats, you need to throw in the mid-September 2005 loss to the Padres. Nats up, 5-0, bottom nine, still in the Wild Card hunt. Frank bumbles the bullpen, brings in the Chief after a run, and that dillweed Khalil Green hits a grand salami to win it and put the Nats out of the race. Come to think of it, it's all been downhill since that loss too.

Posted by: rodeorob | December 7, 2009 1:23 PM | Report abuse

I think, in terms of a single heart-wrenching loss, MD blowing the 10 point lead to Duke with 54 seconds to go is the worst. I still remember watching it, thinking that it could not be happening.

Posted by: agl132 | December 7, 2009 1:23 PM | Report abuse

agree with @agl132. UMD had that game locked down against their biggest rival in a 'oh-my-god-we're-gonna-get-over-the-hump' kind of way and lost.

steve blake was even named player of the game right before the comeback happened. ugh, just terrible. and to make it worse Duke would come back from 22 down just a few months later to prevent UMD from making the finals.

all of these games are just horrible though. yuck.

Posted by: olsonchr | December 7, 2009 1:33 PM | Report abuse

I understand why you picked the game you did, but I think the Maryland game has to be first.

Posted by: ZachMorris | December 7, 2009 1:34 PM | Report abuse

The Flyers loss was tougher for me because it was sudden death. The Caps just folded up against the Pens so early that I had the whole game to come to terms with it. Sure, the loss of the series was a bigger disappointment given that 2008 was surprising playoff run while 2009 was expected, but the anti-climax took some of the edge off, while the Flyers was a dagger of pain.

Posted by: false_cause | December 7, 2009 1:39 PM | Report abuse

Can throw out the Mason loss to Florida, and that's coming from a grown man who wept openly at the end of every win leading up to it. We just never had a chance.

It's the same reason Redskins and Wizards games don't hurt- we don't expect to win.

The Caps' losses are the worst, by far.

Posted by: bryc3 | December 7, 2009 1:41 PM | Report abuse

Yeesh, just shows Suisham was missing big kicks 2 years ago, just like now. He's a prince of a guy, and he's great at kicks that don't matter, but hopefully next year will bring a FG kicker with Moseley/Vinatieri style clutchness.

Posted by: blackjack65 | December 7, 2009 2:04 PM | Report abuse

since I watch 80+ Caps games, way past the # 4the Skins and Zards, it'd be last years Pens loss or the Flyers b4; both were depressing.

Posted by: Max231 | December 7, 2009 2:05 PM | Report abuse

The Skins losing to TB in 2000 was rough. I remember the incomparable Brian Mitchell returning that kickoff for a TD. I thought we were headed for bigger and better things. For Conway not even to get that kick off = hearbreak city.

Posted by: DCinNYC | December 7, 2009 2:13 PM | Report abuse

The Flyers loss hurt more than the Pens loss because it was overtime and there was a questionable non-call of goalie interference and it happened so quickly. Sure, losing to the Penguins is always terrible, but the Caps were soundly beaten in Game 7. The pain was the season ending, but not that the game could have been won if a couple breaks had gone their way.

Glad Dan included the 2003 Tampa game--that was a remarkable combination of every Caps gut-wrenching playoff loss of the previous 20 years. They lose a 2-0 series lead (winning those two on the road!), lost a multiple overtime game on a bizarre penalty, couldn't get scoring when needed from their top-scoring players, etc. But the loss (and the poor attendance for that game, and other factors) was the first step in the dismantling of the team the following season--which ended up leading to the draft of Ovy the following year, so it all had a happy ending.

Posted by: TheFingerman | December 7, 2009 2:15 PM | Report abuse

To "readily" come up with this list just the day after, to make us remember and relive most of these horrific moments, Dan must be hideously sadistic.

Posted by: KarK | December 7, 2009 2:21 PM | Report abuse

Welcome to Washington. Where "NOT POSSIBLE!" is a way of sporting life.

Posted by: StetSportsBlog | December 7, 2009 2:51 PM | Report abuse

I know this won't rank for many, but DCU's loss to the Seattle Sounders in this years Open Cup final after getting into a war of words with Seattle's Front Office and then having the arrogance to come up with the "WE WIN TROPHIES" campaign was pretty embarrassing.
Just sayin'.

Posted by: DadRyan | December 7, 2009 3:28 PM | Report abuse

In both of those losses to Dook in 2001, the Terps took it where-the-sun-don't-shine. As a matter of fact, that loss in the Final Four was probably the most outragously officiated game I've ever seen. Never before have I seen BOTH teams walking to the other end of the court after a foul call only to be called back by the refs.

The entire Caps-Penguin Scum series was officiated in the exact same way. By the time Game 7 rolled around the Caps were scared to go into the Penalty Box and the Penguin Scum knew they could do whatever they wanted. And they did drawing not a single penalty call against them in the game.

Posted by: CapsNut | December 7, 2009 3:34 PM | Report abuse

The final two minute Maryland collapse definitely deserves to be higher. Although an actual DC team, I don't think Georgetown has connected with the entire region since the early 90s and the original John Thompson. I wanted Davidson to win that game. It was an upset, but many in the region were pulling for it.

Posted by: sitruc | December 7, 2009 3:42 PM | Report abuse

I'll second DadRyan. The nature of the defeat made it worse; Seattle sliced us up, and 2-1 was a flattering scoreline. Going into the game, United had not lost at home all year to an MLS opponent. We were also the defending champions.

Posted by: Chest_Rockwell | December 7, 2009 3:52 PM | Report abuse

Enough Steinberg-in-the-shower imagery already!

Posted by: mgv4232 | December 7, 2009 4:24 PM | Report abuse

It would be interesting to compare the most heartwrenching vs heartwarming list. I have a bad feeling the heartwretching would be a lot more memorable than the heartwarming.

Posted by: mcupperman1 | December 7, 2009 4:33 PM | Report abuse

How can you forget the 1999 Cowboys vs. Redskins game where we were up by I think 3 TD's in the 4th. They tie it up and in ot, we lose to a play action bomb to Rocket Ismail. That has to be top ten.

Posted by: kendallreeves | December 7, 2009 4:38 PM | Report abuse

Terps losing that lead in the last second would be my #1 on a list like this. But all of these are awful. The Penguins game seems out of place though, I agree with whoever said it didn't hurt as much because of how lopsided it was from the beginning of the game. Overtime losses hurt more than that one did.

Posted by: Hobes | December 7, 2009 6:28 PM | Report abuse

Dang it all, I sort of agree on the Penguins thing. I allowed myself to get talked into that one. The thing was, the previous year, no one had too much in the way of expectations. But the blowout sure did lessen the pain in the end.

Oh well, bad job by me on that one, I'll admit.

Posted by: DanSteinberg1 | December 7, 2009 6:59 PM | Report abuse

@kendallreeves- It's heartbreaking losses in this decade.

I can't beleive that Game 6 of the 2001 Eastern Quarters vs. Pittsburg is not very high on this list. That was the game where Sergei Gonchar lost the puck coming through the netural zone in overtime and Straka got a clean breakaway, sending the Caps home for the second consecutive year thanks to Pittsburg. I was pretty devestated after that one, much more than anything on the list above.

Posted by: rademaar | December 7, 2009 7:03 PM | Report abuse

also everyone forgets that before Suisham's missed FG in that playoff game Cooley dropped a pass on the ONE YARD LINE!!!

Posted by: goskins1982 | December 7, 2009 10:47 PM | Report abuse

Glad I read this, if only to thoroughly enjoy the words "loathsome Crab Dribbler".

Posted by: werdnahall | December 8, 2009 5:19 AM | Report abuse

there is no way the two time outs game even makes this list, get real

Posted by: JohnnyBlades | December 8, 2009 7:20 AM | Report abuse

@goskins82 -- I forgot about that. I feel worse now than I did yesterday. Thank you.

Posted by: DCinNYC | December 8, 2009 8:33 AM | Report abuse

Losing to Duke in the Final Four is so high on my list.


Posted by: JohninMpls | December 8, 2009 8:52 AM | Report abuse

I hope this depressing article don't ruin my hold day. So much heartbroken sports stories for one city to handle. Hopefully, the CAPS can pull it off this season. GO CAPS.

Posted by: instinct227 | December 8, 2009 8:59 AM | Report abuse

Caps loss to the Flyers in 2008 was far more depressing than the one to the Pens last season. The 2007-2008 season was so much more emotional, with the Caps going from worst to first, winning the division in Game 82 and then fighting like hell to beat the Flyers. The OT sudden death loss was heartbreaking and I actually cried from the disappointment.

Last season's playoffs were much different. The Caps were limping through Rounds 1 and 2 and anyone who thought they had a strong chance of winning Round 2 had their Rock-the-Red-colored glasses on and was not really paying attention. The Caps would never have made it through a Round 3.

Posted by: CapsChick | December 8, 2009 9:36 AM | Report abuse

losing to the penguins again trumps any other caps playoff loss. period.

flyers is more heartbreaking than lightning because it's the new iteration of caps - not the jagr commies.

Posted by: CF11555 | December 8, 2009 10:56 AM | Report abuse

and had they beaten the penguins:

they would have made it to the SCF finals (beat Carolina in 5 easy) and gotten clobbered by Detroit.

Posted by: CF11555 | December 8, 2009 10:59 AM | Report abuse

I thought last years game 5 home loss against the pens was worse than the game 7 drubbing. Up 2-1 going into the third, the pens score 2 straight and take a 3-2 lead. Ovechkin scores to tie it at 3 and send the game into OT. Then in OT, disaster ensues; Steckel flubs a wide open game winning goal, then the non-call on Semin being tripped leads to the odd man rush for the pens and the pass is deflected into the goal by Poti.


Posted by: zyvo23 | December 8, 2009 2:34 PM | Report abuse

How can you forget the 1999 Cowboys vs. Redskins game ...

I don't think 1999 was in this decade.

Posted by: larryn703 | December 8, 2009 2:47 PM | Report abuse

Penguins 3, Caps 3 (April 24, 2001)...? Had to look that one up. It was actually Pens 4, Caps 3. Thanks for bringing up these games everyone was trying to forget. Is there a heartwarming DC wins of the decade post not too far away?

Posted by: larryn703 | December 8, 2009 2:51 PM | Report abuse

Wow, what memories! You are the ultimate masochist. Made me think of past decades of suffering by DC fans, like the Clint Longley Cowboys Thaksgiving horror show.

One of my worst was in the late '70's. The Caps had never beaten the Flyers. The streak had gone on for four or five years. Finally, one night at the Cap Centre, we were leading four to three when, with 4 seconds on the clock, Bobby Clarke scored to tie it. (No OT in those days). That's the first and only time I've really lost it--just about got in a fistfight with some Flyer fans who were rubbing it in.

Posted by: StevefromSacto | December 8, 2009 3:59 PM | Report abuse

Dan, now that you've gotten us depressed, we need cheering up! How about a list of the 10 greatest moments of the decade? (Hopefully you can find 10).

Posted by: StevefromSacto | December 8, 2009 5:35 PM | Report abuse

Thanksgiving Day versus the Cowboys. Clint Longley, the Mad Bomber to Drew Pearson. It ruined Thanksgiving that year, and the bad memories of it still haunt us to this day. Not one year at Thanksgiving does that day not get discussed. It was enough for 5 decades of grief and heartache, not just for this decade.

Posted by: terpmitch | December 9, 2009 3:33 PM | Report abuse

Let's not forget that in the same year as the loss to Tampa in the playoffs caused by a botched field goal, the Skins had a let down on a similar play against Dallas. A botched field goal ended in a loss.

Dallas answered a 22 point Skins 3rd quarter with a 21 point 4th quarter. Conway had a chance to win the game in regulation but a bad snap/hold dashed those hopes and sent the game to overtime where Aikman found Rocket Ismail for the game winning, 76 yard TD.

Had the Skins made the field goal in regulation, they would have picked up another win and the Tampa playoff game gets played at FedEx.

Posted by: kevin_rigsby19 | December 10, 2009 6:37 AM | Report abuse

I would like to add the Terps football loss to Wake. I believe we were up three touchdowns late in the 3rd quarter when Steffy was picked in their endzone and it was ran all the way back. From then on, every Terps fan knew it was a battle to beat the clock. We lost in overtime.

Posted by: aviscardo | December 11, 2009 2:03 PM | Report abuse

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