The 25 greatest Gotham villains of all-time

GOTHAM: L-R: Robin Lord Taylor as Oswald Cobblepot / Penguin, Cory Michael Smith as Edward Nygma / The Riddler, Donal Logue as Detective Harvey Bullock, Ben McKenzie as Detective James Gordon, David Mazouz as Bruce Wayne, Chris Chalk as Lucius Fox, Camren Bicondova as Selina Kyle / the future Catwoman, Sean Pertwee as Alfred Pennyworth and Erin Richards as Barbara Kean. Season 5 of GOTHAM premieres Thursday, Jan. 3 (8:00-9:00 PM ET/PT) on FOX. ©2018 Fox Broadcasting Co. Cr: JUSTIN STEPHENS / FOX
GOTHAM: L-R: Robin Lord Taylor as Oswald Cobblepot / Penguin, Cory Michael Smith as Edward Nygma / The Riddler, Donal Logue as Detective Harvey Bullock, Ben McKenzie as Detective James Gordon, David Mazouz as Bruce Wayne, Chris Chalk as Lucius Fox, Camren Bicondova as Selina Kyle / the future Catwoman, Sean Pertwee as Alfred Pennyworth and Erin Richards as Barbara Kean. Season 5 of GOTHAM premieres Thursday, Jan. 3 (8:00-9:00 PM ET/PT) on FOX. ©2018 Fox Broadcasting Co. Cr: JUSTIN STEPHENS / FOX /
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23. Nathaniel Barnes (The Executioner)

Portrayed by: Michael Chiklis

First appearance: “Rise of the Villains: Strike Force”

Nathaniel Barnes was a good guy turned bad. He was a marine and worked his way up to being captain of the Gotham City Police Department. He had a decent streak while he was at the GCPD, but it started going downhill after his encounter with Azrael (Theo Galavan).

After the attack by Azrael, Barnes was relegated to walking around with a cane. This limited mobility meant that he’d spend more time in his office than he did before. His bad luck continued when Jervis Tetch brought the Terrible Tweeds with him to attack the GCPD in order to get to his sister Alice. In the chaos, Alice dies and a drop of her blood gets into Barnes’ eye.

That moment is when Barnes begins his turn into the Executioner. He’s powerful and no longer needs the cane. He also thinks that he should just get rid of the criminal scum by killing them without a fair trial. However, he eventually wants to kill Jim Gordon and says as much to Leslie Thompkins.

His journey doesn’t end there, though, because the Court of Owls gets their hands on him. He then goes to the GCPD and has his hand blown off by Gordon. He escapes custody on his way to Arkham and his storyline never quite reached a finality we were hoping for.