On January 11 in SILK #16, it appears the venerable J. Jonah Jameson has struck an alliance with—or perhaps sworn allegiance to—The Jackal. While this might shock some, Jameson has a long history of associating with some pretty shady characters when it suits his purposes. We look back on some of the higher profile bad choices the mustachioed man from the Daily Bugle has made.

To Slay a Spider
When Spencer Smythe goes door-to-door to promote his brand, Jameson initially turns away the clearly mad scientist on account of him being clearly mad. However, Triple J cannot help himself and before long he has the remote control to guide Slayer and uses it to follow Spidey around the city.

When the time comes to strike, the Slayer initially proves quite the tool, preventing the Webhead from attaching to walls and, eventually, ensnaring Spider-Man. In the end though, defeat gets snatched from the jaws of victory when Peter Parker, even while captured, figures out how to mess with the robot’s circuitry, shutting it down.

Once More, With Feeling
Despite his general disposition, Jameson apparently has a hidden optimistic streak because he went back to Smythe for another Slayer without any evidence to suggest that this had become a better idea from the last time he tried.

Ultimately, this go around, JJJ got overruled by his mad scientist colleague who would not be satisfied with a simple W. Instead, Smythe seized control of the machine from the newspaper man and forced the issue, hoping to utterly disgrace the arachnid. By pressing his advantage however, it allows Spider-Man to prolong the fight and bombard the robot with so many spiders, it became too overwhelmed to work.

Surely Third Time Will Be a Charm Though
Apparently deciding only a spider can beat another spider, the Smythe-Jameson duo took their act on the road one more time, this time with a Slayer that looked like the eight legged creature it so hated.

Predictably, Smythe took control of the robot from Jameson once again. This time, however, Smythe—doing the thing that Jonah apparently cannot and learning from past mistakes—settled for knocking out the Webslinger and stealing some lab equipment instead of trying to definitively ruin Spidey.

A Shady P.I.
While his actions sometimes suggest otherwise, J. Jonah Jameson has smarts. Those smarts led him to realize that there could be more than one way to defeat Spider-Man and if the route of physical violence seemed to be a no-go, perhaps an old fashioned unmasking would work.

To that end, JJJ went to the phone book and searched for “Amoral Investigators” and found Mac Gargan as the first listing. Gargan, who loved money more than doing the right thing, took the job straight away. While he failed, he and Jameson’s bond led to a far bigger assignment.

Know Thy Sting
Sensing that while he proved unequal to the task of discovering who dwelled under the mask of Spider-Man he might still prove useful, Jameson approached Gargan and offered him another opportunity: a painful, highly experimental technique that could turn the P.I. into a super powered individual himself. Or could leave him dead.

Gargan decided “could” felt good enough to him and agreed. He survived the process to emerge as The Scorpion. While the emerald clad super villain did prove quite successful at first, Spidey quickly got his number and that, combined with Gargan’s increasingly precarious mental state, left him with a huge grudge against Jameson and a life as the Wallcrawler’s punching bag.

Seriously, Again?!
While Jameson and Smythe parted ways after the third Spider-Slayer, it seems that JJJ remained enamored of the concept, if not the scientist making them. So when a chance to still use the name and goal came without Smythe attached to, Jameson hopped on-board right away.

This fifth Slayer resulted from a collaboration between Jonah and future wife Dr. Marla Madison. Proving that JJJ went into journalism not engineering for a reason, the Slayer ended up done in by a falling statue, despite attacking Spidey at the same time as Will O’ the Wisp.

Osborn’s Stooge
Blackmailed and fearing for his family’s life, Jameson agrees to let Norman Osborn seize control of the Bugle. Acting as a sort of PR wing for Osborn, JJJ quickly began to crack under stress and knowing his very actions ran aground of journalistic ethics.

Nearly driven to murder by the experience, Jameson ends up saved by Osborn’s own deteriorating mental health. Forced underground by the Goblin serum’s deleterious effect, Osborn gives up the Bugle along the way, getting Jameson out from underneath the super villain’s thumb and keeping the newspaper man from going too far down the path he found himself on.

See what the future holds for J. Jonah Jameson in the pages of SILK!