Heartbreak And Highlights – Growing Up A Portland Trail Blazers Fan In The Age Of YouTube

Until Damian Lillard hit the “Shot” to win the series against the Houston Rockets in 2014, being a Trail Blazer fan was an exercise in misery. Boston’s Sox will always remember Bill Buckner, Cleveland’s Cavs will always remember Jordan’s fadeaway, Chicago Cubs fans will always remember… A goat I guess?

But (homer bias alert) for me the Trail Blazers stand out for sheer dumbfounded bad luck. Despite wasting picks on nil-players like Sam Bowie and Greg Oden the Blazers were still contending for championships throughout the 90s and early aughts. Unfortunately their peaks always happened when there was someone just a little better.

Let me give you some examples.

(Kobe/Shaq bs oop)

In the Spring of 2000 the Portland Trail Blazers looked like NBA royalty. With a roster that included such single names as Pippen, Sabonis, and Sheed the Blazers were poised for greatness. Then came a 4th quarter and a moment that lives on in every playoff highlight reel that has since been produced by the NBA; the ‘oop’ heard round the world. Shaq running up the court like a dreamliner jet, Kobe with what would become a trademark smirk.

(The shrug)

In the Spring of 1989 The Trailblazers boasted Porter, Drexler and Mr. Mercy Kersy. Their defense could have defined a generation of basketball talent. Unfortunately Michael Jordan hit six three pointers in the first half and then came “the shrug.”

Bam. Another NBA iconic moment born from the pain of the Blazers; and the list goes on.

Robert Horry’s dagger in game 7 after the Blazers were poised to be the first professional sports team to complete a 3-0 series comeback (two years before the Red Sox accomplished it.) Brandon Roy’s performance versus the Mavericks only led to the revelation that his knees were like Greg Oden’s career: both never really there and over too soon. A death of a thousand cuts is the life of a Trail Blazer fanatic.


It is the nature of sports to be cruel. Nature is a mean mother. For me, though, the misery and heartbreak is why I watch. Because you never know what is around the corner.

In 2004 the Red Sox were losing by 6 runs going into the bottom of the 9th versus the Yankees and people started to leave. They missed out on one of the greatest regular season comebacks of all time and they will only ever be able to say that they “almost” saw it. I will always watch a game to the end, because you never know what you might miss…

(Dame game winner)

TLDR: Unless you’re on a bandwagon, being a fan hurts so bad you can’t help but fall in love.