- "Your friend may look like a man, but he is unquestionably a monster. Everyone here is a monster. And if you insist on continuing to bait them, I guarantee you, you will get mauled."
- —Gregory Wolfe to Barry Allen[src]
At some point in time, Gregory become the warden of Iron Heights Prison. Under his supervision, a special cell was built for James Jesse in 2010 after he had talked his psychologist, who was visiting weekly, into committing suicide.
In 2018, Wolfe met Barry again in different circumstances, this time as Barry was sentenced for life in Iron Heights.
Wolfe soon became suspicious of Barry after seeing he had made friends with David "Big Sir" Ratchet. Barry's continuous interactions with Big Sir irritated Wolfe, as he saw Barry's trying to instill hope, and warned him to back off. Soon after, he installed another security camera directed at Barry's cell. As a result, he discovered that Barry is the Flash after Barry freed Dave, unaware of the camera. He then revealed this knowledge after drugging the pudding that Barry was eating and relocated him to the meta-human wing of Iron Heights. Wolfe called Amunet Black, stating that he's got a big catch for her.
Wolfe found that Barry and four other metas had escaped on the day he was to sell them to Amunet, but with some guards, he cornered them in a courtyard. Disabling Barry with an inhibitor collar, he was prepared to face off against the other metas when Becky Sharpe used her powers to knock them down. Amunet arrived, disappointed with Wolfe's failure, but Becky used her powers to knock out Amunet and all the guards as well. Suddenly, the Thinker appeared and stole the minds and powers of the meta-humans except for Barry. He moved on to Wolfe, who defiantly exclaimed he would never take him. However, DeVoe replied that he only wanted Wolfe dead and promptly killed him.
Wolfe's misdeeds were initially unknown to the people of Central City, especially Mayor Van Buren, who claimed to the people that the corrupt warden had died a hero. However, after Iris West published her articles revealing all of DeVoe's crimes, she also exposed the truth about Wolfe, including him illegally trafficking meta-humans for profit.
Initially, Wolfe seemed like an honorable and reasonable individual as he warned Barry Allen that it would take him a while to get used to prison and urged him not to help the other prisoners, as it could put him in danger.
However, it was later revealed that Wolfe was greedy, ruthless and corrupt, as he used his official position to sell meta-humans to Amunet Black for profit without regard as to what means Amunet would use them for. Wolfe has a strong sense of pride, as he makes sure to personally deal with Amunet and her associates on equal terms.
Wolfe was proven to be a coward who preferred to hide behind others; upon realizing he was outnumbered by the meta-humans who wanted to attack him as revenge for trying to sell them, Wolfe chose to reveal the identity of the Flash just to save his own skin, which didn't work out in the long run.
- Psychologist: Wolfe was seen knowing exactly how to treat James Jesse, building a special cell for him and using licorice to facilitate questioning him.
Behind the scenes
- In the DC comics, Gregory Wolfe is the warden at Iron Heights, but he is also a metahuman with the power of psychokinesis. Wolfe is able to cause muscular spasm in people by tightening or loosening their muscles; he uses this ability in his work, whether making rioting inmates collapse through temporary muscle spasms or loosening the pain in Hunter Zolomon's damaged knee so that he could run while escaping Grodd's forces.
- In the DC comics, Gregory is African-American. The Arrowverse version was portrayed by Caucasian actor Anthony Harrison in Season 1, but the role was given to African-American actor Richard Brooks in Season 4.