I started writing my year end Email Fail wrap up post several weeks ago.

I got as far as the title. Don’t you think  The Year in Email Failure is catchy? Then I sat down to get my post written and discovered that Chris Hoke’s Ten Worst Email Gaffes of 2009 beat me to it.

I’m on board with most of Hoke’s picks. But I thought I’d go through the Email Fail archives and revisit some of my favorites.

Check these out:

• The Governator’s creative email to members of the State Assembly.
• The state employee who lost his job for sending rude emails complaining about police road blocks (while on the job and because he had been caught in possession of drugs by one of said roadblocks).
• The weatherman who lost his job, thanks to his roommate sending threatening emails to his morning show co-host.
• The company who sends an email saying “Hey, we know we’re not supposed to email you. Are you happy with this arrangement?
• Securities fraud by SEC lawyers, using their SEC email accounts.
• Classmates.com emails Class of ’83 with appeal to join and reconnect with long-dead classmate.
• The mean boss sends a crabby email to his staff, and gets raked over the Twitter coals.
• A state senator berates a struggling student for her poor use of punctuation.

I bet government officials are used to getting emails ranting about their policies and actions. And I bet a lot of taxpayers have legitimate gripes when they send those rants.

But I had to laugh when I read this one:

An Oklahoma City man was arrested for marijuana possession after he got stopped by sheriff’s deputies at a traffic roadblock/checkpoint. Officers were looking for drunk drivers when they arrested Evan White and charged him with felony possession with the intent to distribute.

Evan White, victim of his own Email Fail, photo from New9.com

So White sends an email to the sheriff a few days later, calling him a hypocrite and saying:

It’s a shame that he puts the citizens of Oklahoma through such nonsense in the name of ‘saving lives’ when the real reason for resorting to fishing with a fishnet is the almighty dollar and nothing else.

To clarify, White believes the roadblock was set up to raise money for the state, not to get drunk drivers off the roads. And he’s concerned enough about the citizens of Oklahoma to write a nasty email to the sheriff about it.

Of course, in his ranting email, he doesn’t mention that he was one of those who got snagged breaking the law in that roadblock. Oh, and he also doesn’t seem to think the citizens of Oklahoma would mind paying a state worker to use state computers to do their ranting about their unfair drug arrests!

Yes, that’s right. White is a state employee, and was on state time when he wrote his letter from a state-owned computer.  And the sheriff calls him on it in his reply. You can read the entire exchange here, including the part where White goes to a different computer, logs in to a different email address, and is sort of contrite about the whole thing.

And the icing on the cake  is that White ended up losing his job! So now he’s facing drug charges, unemployed AND a victim of a pretty big Email Fail.

I almost feel bad for him.

Almost. But not quite.