My Top 10 Most Painful Sports Losses (Part II: 1-5)

Click here to see #s 6-10 on this list

These are the losses I’ll never forget…the worst of the worst…the ones that made me literally want to stop watching sports. Oh wait, we know that was never going to happen…

You’ve already read about a Cubs collapse, Arizona Basketball’s Elite Eight failures, a Packers overtime debacle, and a UofA football meltdown. Unfortunately all are featured again in this nasty top 5 (for me at least).

The only way to separate #s 1-5 are by the “sting factor.” How irritated do I still get when these games are mentioned? If you don’t like my favorite teams, something tells me you’ll really enjoy this list…

5. NFC Championship Game: Giants 23, Packers 20 (OT) (1/20/08)
Brett Favre was my favorite player growing up. If I had a shred of athletic ability, that’s who I would’ve aspired to be on the playing field. He was one drive away from playing a Super Bowl in my hometown. Unfortunately his last pass as a Green Bay Packer had a different outcome.

The wind chill in Green Bay was -23 degrees that night and it’s amazing to me how many players wore short sleeves (just look at the picture above). The Packers should’ve won that game despite the fact that the Giants outplayed them for most of the 68 minutes they played. 

The Super Bowl is my #1 sports bucket list item and had the Packers played, it’s likely I would’ve had a free ticket to the game on my 25th birthday weekend. I would’ve seen Tom Brady’s 18-0 Patriots team take on Brett Favre’s Packers. It would’ve been a matchup for the ages.

And then Favre threw an out route right to Corey Webster and the rest is history. I never went to Super Bowl XLII nor have I been to the big game since…

4. 2005 Midwest Region Final: Illinois 90, Arizona 89 (OT) (3/26/05)
This game is likely #1 on a lot of Arizona basketball fans’ lists and therefore I may have it a few spots too low on my list. When I think of choke jobs, this one takes the cake. The Wildcats led by 15 points with four minutes to go – a seemingly insurmountable lead. And then the Illini couldn’t miss. Usually when a team goes on a crazy run, the opposing coach will use one or multiple timeouts. Unfortunately Lute Olson, for as great a coach as he was, bungled this one to holy hell. 

I was a senior at UofA and remember vividly watching the game at a house party. Despite the brutal loss, I tried to go out in Tucson that Saturday night but sadly the bars had been deserted. 

A senior-laden team, led by Channing Frye and Salim Stoudamire, that deserved better than two Elite Eight appearances unfortunately ended their careers here.

Warning: this video below is not for the faint of heart (or ASU and Illini fans)…

3. St. Louis Rams 20, Dallas Cowboys 10 (1/1/06)
Box Score
You’re reading this thinking, “how does a meaningless 2005-06 Week 17 game between two lousy teams factor on this list?” Two words: fantasy football.

I’ve run my own league since 1997…we’re going into Year 21 and my lack of success is mind-boggling. This was a total points league and ran through the final games of the season – all 256 regular season games impacted the final result. In my league this was a two team race and as it turns out, I had the final player left to decide things. I was down by less than 9 points and I had Rams star wide receiver Torry Holt left to play. Going into the final Sunday night game of the season, Holt had 98 catches for 1,291 yards and 9 touchdowns. With each reception worth a point and the yards worth one per every 10 receiving yards, this should’ve been an easy win for me.

At halftime, Holt had 3 catches for 37 yards. Being that the game was tied 10-10 and all I needed was two more catches, I ordered a celebratory drink at TGI Friday’s where I was watching.

Late in the 3rd quarter, Holt caught a pass for 3 yards. I was THIS close to my first fantasy football championship.

With 3:47 left in the game, “Big Game Torry” as he was known took a reverse for a two yard gain. After a timeout, quarterback Jamie Martin attempted to throw a screen pass to Holt which he dropped. My stomach sank.

St. Louis punted and didn’t throw the rest of the game. This is how my fantasy football season turned out:

Screen Shot 2017-05-29 at 10.04.45 PM

Despite having made my league’s championship game the last two years, my record stands at 0-20 in years winning the league.

To his credit, thanks to a humorous Twitter and later radio exchange, Holt did somewhat apologize. That has to be worth some consolation, right?

Screen Shot 2017-05-29 at 10.14.47 PM

2. 2003 National League Championship Series Game 7: Marlins 9, Cubs 6 (10/15/03)
Most Cubs fans would say that the 8th inning of Game 6 was more painful. This time, I’ll disagree. For the record, I don’t blame Steve Bartman for what happened with the infamous fly ball. I blame Moises Alou for throwing an unnecessary tantrum which then flustered Mark Prior and I blame Alex Gonzalez for booting a routine ground ball. I also blame me…for putting the champagne on ice between the 7th and 8th innings.

So the Cubs lost Game 6…the NLCS was tied up at 3 games each and the Cubs still ace star pitcher Kerry Wood on the mound in Game 7. 

In the Summer of 2003 I interned at KCUB 1290 AM in Tucson and though my internship was over, host Rich Herrera called me live on his radio show to make a wager. If the Cubs were to lose, I agreed to walk around University Ave. and part of campus with a sign that said “The Cubs are losers and so am I.”  I was sure Game 7 would turn out like Games 2,3, and 4…Cubs wins.

Wood homered to tie the game in the bottom of the 3rd inning and a 2-run Moises Alou shot put Chicago up 5-3 through four innings. The lead last until the 5th inning when the Marlins put up 3 runs – they were just a machine from the 8th inning on those last two nights.

When the game finally ended and the Cubs World Championship drought officially reached 95 years, I literally couldn’t function for the rest of the night. 

And yes – I carried that sign around for an afternoon the following week. Fortunately no pictures were ever taken (to my knowledge).


1. Arizona State 30, Arizona 29 (2OT) (12/2/10)
Contrary to popular belief, no sporting event has ever made me cry. This one came the closest. I have never left a stadium in my entire life feeling so sick, disgusted, annoyed, and upset all at the same time. As of 2016, I’ve been to 17 UofA-ASU football games and more than half the time ASU has won unfortunately. But this one…it was different.

ASU was ahead most of the 4th quarter until Nick Foles rallied the Cats with :27 seconds left to tie the game at 20. Most likely an extra point would win the game for UofA. But James Brooks reached out to block Alex Zendejas’ kick and the game moved to overtime.

Miraculously it seemed, Zendejas made a short field goal which was matched by ASU to end the first overtime at 23-23.

In the second overtime, the Sun Devils and Wildcats traded rushing touchdowns. Now what would the Wildcats do? From Section 24, Row 36, Seat 6 of Arizona Stadium, I implored the ‘Cats to go for two. I wanted Coach Mike Stoops to do what he didn’t against Oregon in 2009. But he proved to be gutless, instead opting for the game tying extra point to extend the game further.

I heard the thud before my brain processed what was happening directly in front of me. The kick was blocked…again.

The usual trip home of around 100 minutes took nearly twice as long that night. It was the universe torturing me further.

A 7-1 start to the 2010 season ended up 7-6 after a wretched performance against Oklahoma State in the Alamo Bowl. Stoops was fired midway through 2011 which I truly believe wouldn’t have happened had the Wildcats won the ASU game the year before.

Postscript: Fortunately the Cubs won the World Series in 2016, the Packers won a Super Bowl in 2011, and UofA football defeated ASU to win the Pac-12 South Division title in 2014. Those victories SLIGHTLY eased the pain of those prior losses.

Unfortunately Arizona basketball hasn’t advanced past the Elite Eight since 2001 and my highest ECFFL fantasy football finish has been 2nd place (four times).

Here’s to hoping for better success and no more additions to this list anytime soon!


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