I worked my way through college driving a truck and made decent money for a college kid back in the late 70's/early 80's doing that, so I never really needed the student loan $$$ as tuition rates and cost of living were a shyte ton lower back then than they are now. I decided to take out one $3K student loan (max allowed back then) as "mad money / party money" and unfortunately I received it right before the "lock of the year" came through from an East Coast betting service several guys in my fraternity house were "subscribing" to. So naturally, I did the smart thing and put the entire $3K on the upcoming "lock of the year" MNF game in favor of Buffalo.
The Bills - favored by 7.5 points - rewarded my savvy investing by getting the shit kicked out of them. IIRC, they fumbled the opening kickoff for a "scoop-n-score", then Jim Kelly tossed a pick six on a screen pass on the 2nd or 3rd play from scrimmage. It didn't get any closer as the game went on. There were guys in our "TV room" at the house that legitimately needed the $$$ for school, rent, food, etc. Collectively, we lost $17K on that game in the room that night and it was a morose and depressed group.
I did the only thing I could think of to do: I stood up and delivered a drunken, stupid Blutarsky-esque speech about "never in the history of our fraternity have so few lost so much on a single football game. This calls for a celebration. Let's go to the bar and I'm buying!" So we all trudged out of the house and walked down to the Chicago Bar and drank until they threw us out at closing time. My brothers celebrated by "leadership under crisis" by electing me fraternity President the next Sunday. True story.
In the memo field of the checks I scratched out to pay off that student loan, I always wrote, "Buffalo - Monday Night" as a reminder to myself of my stupidity. I haven't gambled* since, so it may have been money well lost at a formative stage in my life.
* This "no gambling" statement does not include unprotected sects or the stock market