WARNING: This article contains major spoilers for Titans #20 by Dan Abnett, Paul Pelletier, Andrew Hennessy, and Adriano Lucas, on sale now.
Now that the Justice League have disbanded the Titans in a bid to stop Donna Troy from groing into the villainous Troia, it's every hero for himself. Roy Harper, aka Arsenal, has elected to use his newfound freetime tracking down the suppliers of a powerful new drug called Bliss, following a lead on counterfeit batch in the hopes it will lead him to the real thing. As it so happens, his ex-girlfriend, the assassin Cheshire, has accepted a contract that leads her along a similar path.
After teaming up to take down some drug dealers, Arsenal and Cheshire's reunion flows from friendly to romantic -- but then turns into something else. Something very dark.
It doesn't get much lower than drugging a recovering addict to make him think he's relapsed.
Roy Harper, famously, is a former heroin addict, a vice first introduced in Green Lantern/Green Arrow #85 by Dennis O'Neil and Neal Adams. Though he's overcome his addiction, it is a constant struggle, one that has stuck with the character through DC's multiple continuity shifts. Just before Flashpoint and following his daughter's death in Justice League: Cry for Justice, Roy relapsed, though (thankfully) this does not seem to have carried through in the current Rebirth universe.
In Titans #20, Cheshire plays Roy perfectly. First, she arrives in the nick of time for to rescue him, taking down a group of thugs surrounding her ex. Then, she checks in on his current frame of mind and his support system via a casual "date."
Learning that the Titans are no more makes Jade's job easier. Especially when Roy, phoning Donna at the Justice League Watchtower, tells her he'll be "going dark" for a time. He's cut off from his friends.
One more mission, where they recover the original sample of Bliss that both had sought, and it's time to celebrate. Romantically.
There's the moment. Poison in the fingernails, and Roy wakes up feeling rough to an apartment staged to look like he's "fallen right back down into the pit" of drug abuse. This is all a cover to hide the fact that she's also stolen the Bliss sample, delivered to Monsieur Mallah and the Brain, who appear to be the drug's originators.
This is some extraordinarily cruel gaslighting, and elevates Cheshire from "one more badgirl assassin" into the upper echelons of DC's most evil villains. It may be on a smaller scale than, say, Darkseid devastating the Earth, but this sort of ground-level hatefulness that would be viable in the real world is much more unsettling.
Beyond question, Cheshire holds the title for DC's Worst Valentine's Date, Ever.