Ladies and Gentlemen, let me introduce to you our first guest writer and mini-series to ever grace the pages of Caught Looking. Scott O’Leary has been a good friend of mine since the days of grade school when the most pressing topic to discuss at the time was “What’d you do in math today?” Things have obviously changed since then, we aged, grew up, went to different universities and entered the world of work in completely different fields. But we’ve always remained great friends, mostly thanks to the constant of sports among other things (mostly beer).

Growing up in Western Pennsylvania, we’ve rooted for the same hometown teams since the early 90’s…well until the summer of 2010. You see, Scott is just one of many disgusted Pirates fans in the world, but he’s going a different route to voice his displeasure—he’s throwing in the towel on the Pittsburgh Baseball Club.

I won’t spoil any of his plans now and will allow Scott to explain himself below, but as a fed up Pirates fan, I can not blame him for the direction he’s going. I’m still a fan today and will be years down the road because I believe the franchise and its history is bigger than the incompetent ownership and pray that change is on the way, but after watching 17 consecutive seasons of futility, 1,001 different ways to lose a baseball game, front office blunders and numerous trades and fire sales, I have a hard time trying to defend the worst run franchise today in any sports. I understand the viewpoint on those fans, and that’s why Scott’s idea brought excitement that he was getting out finally, so I asked him to share his adventure with the blog periodically throughout the season. Without further ado, here’s Scott O’Leary to explain himself and the Random Fandom…

I picked a bad day to become a baseball fan. Tuesday, April 6, 1993. A date that will live in infamy.

As a child, my Dad wasn’t that into sports, so naturally, neither was I. Growing up, I never remember a baseball game being on TV at home, and to this date I don’t think my Dad and I have gone together to more than two baseball games ever. On Sundays during the fall he’d have the Steelers on if they were playing, but as a rule we weren’t a football house. As for hockey and basketball, I think I found out the truth about Santa Claus before I knew those sports even existed. Suffice it to say, if I was going to become a sports fan, it was going to be an endeavor I’d have to undertake alone.

In 1993 I decided that I would teach myself sports. For baseball, being from the Pittsburgh area where the Pirates were the three-time defending NL East champs, becoming a Pirates fan was a natural, obvious choice. My plan was simple really—I’d just watch baseball and pick up what I needed to know along the way. I had some of the basics already under my belt thanks to a year of Instructional League baseball in first grade, and what I didn’t understand I’d just ask my friends. 1993 was a year of great promise, and I was excited to be on board. Boy, did I back the wrong pony.

I remember watching Opening Day 1993 from my living room. As Orlando Merced, Carlos Garcia and Al Martin took the field that day I remember thinking, “This is my team now!” In hindsight, I could not have been in store for more trouble unless my last name was Goldberg and I just moved into a new apartment in beautiful downtown Warsaw, Poland in late August 1939.

Al Martin wasn't Scott's Barry Bonds

What followed was a bittersweet, dysfunctional love affair that continues to present day. For seventeen and a half seasons I have suffered at the hands of Major League Baseball’s most inept franchise. Somehow, through all the losing seasons, bad trades, salary dumps and Dave Littlefield, I remained not only a Pirates fan, but grew to love the game of baseball. I was ten years old on Opening Day 1993, and in past eighteen years a lot has changed: I’m now working on a graduate degree, I drink scotch, smoke cigars, and have a 401(k). However, what has not changed in that time is the losing. I know my story is not much different from that of most Pirates fans my age. However, the fact remains, in my baseball lifetime I’ve never had anything to cheer about. No late season playoff races, no talk of winning the pennant, not a single game of significance played after Independence Day. It’s been painful, it’s been frustrating, it’s been embarrassing, and after today, it’s over.

I’m out.

For the past year I’ve been toying with the idea of something I call, “Random Fandom.” Like most of my ideas, it’s simple really. I randomly choose a MLB team to follow and devote my loyalty to, and it’s my belief that as I pick a new team to follow each year before the season begins I will randomly choose a winner to root for before the Pirates ever come close to winning anything.

This All-Star break is the start of my Random Fandom. I will randomly choose a baseball team to follow for the remainder of this season, and pledge to that team all my energies and loyalty. Thanks to the magic of the Internet and the MLB Extra Innings package, this is an easier task than ever. I’ll learn the history of the team, watch the games live, read the local papers, and wear their cap with pride.

Not only does this give me the opportunity to possibly root for a winner, but expand my baseball knowledge and create an entertaining look into what it means to be a fan.

Yes, I do have reservations about leaving my Buccos behind, and secretly fear that as soon as I’m off the boat they’ll begin to win. But, let’s be honest.  That’s not going to happen. After 17 ½ seasons, who can blame me? Who can blame anyone in my position? The fact that anyone goes to PNC Park to watch the Pirates anymore simply befuddles me. In all honesty, I think the only way the Pirates will ever improve is if everyone in Western Pennsylvania does the same as myself and swears the team off entirely.

Enough about the past. Now is a time to look to the future. By the end of this All-Star break I’ll have a new team, and new lease on my baseball life. It’s something I look forward to, and hope that you’ll want to come along with me on the journey.

Play Ball!

Follow Scott O’Leary on his Twitter page here.