Face-palm #7: Jack downloads gay porn and hands it to a judge. The judge is unimpressed. (2007)

Jack filed a lawsuit against the Florida Bar accusing it of – yep, you guessed it – conspiring against him, this time with long-term legal rival Norm Kent. As well as being a lawyer, Kent runs the National Gay News site, and in an attempt to ‘prove’ what a corruption-reveling deviant he is, Jack made claims that the site was providing hardcore gay porn to readers of any age.

The problem? The porn Jack found was all hosted on sites separate from Kent’s. Jack just collated it from sites referenced in the adult links section of NGN. The bigger problem? Jack took it upon himself to print off reams of digital cock and ram it straight into the judge’s inbox as part of his filing. Surely flowers or a few compliments about his eyes would have been a better start.

And the really funny bit? By submitting the porn to the court, Jack put it on the public record, meaning that it can now be viewed by anyone of any age.

Face-palm #8: Jack submits a home-made craft project in court (2008)

In a protest against what he perceived to be the court’s “inability" to comprehend his arguments, Jack filed a motion in the form of a picture book, presumably to make it easier to understand. It included, amongst many, many others, images of swastikas, kangaroos in court, cartoon squirrels, Paul Simon, monkeys, and Jack Nicholson. The Florida Supreme Court threatened him with sanctions as a result of this and the above palming. Have a look at it here. You know you want to.

Face-palm #9: Jack tells a games journalist to molest children (2008)

During his ongoing correspondence with Destructoid Reviews Editor Jim Sterling, Jack responded to Sterling’s celebration over the decision to overturn the UK ban of Manhunt 2 by asking “Why don't you just molest children directly rather than through Rockstar.  It would be more personal that way”. Way to protect the kids, Jack.