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The Worst Things Resident Evil's Leon Kennedy Has Ever Done

"Resident Evil" hero Leon S. Kennedy is a bit of a goodie two shoes. He first appeared as a rookie cop showing up for the first day of work to a Raccoon City ravaged by a zombie outbreak in 1998's "Resident Evil 2." He would go on to be one of the most recognizable characters in the franchise's long history, starring in "Resident Evil 4," "Resident Evil 6," and related media spanning more mediums than just games. 

Despite his quick wit and a hardened exterior, Leon pretty much always does the right thing without fail. Pretty much. Over the course of a fateful career that has taken the man from the Raccoon City Police Department to a globe-trotting career hunting down bio-terrorists, he has made a handful of critical errors. His decisions and allegiances don't always lead Leon down the right path — and in fact, Leon Kennedy has done a few terrible things in his years of zombie-killing.

He lets Ada Wong cloud his judgement

While not objectively evil or bad (searching for love in the dark world of zombies and corporate espionage is kind of admirable, in a way), Leon's infatuation with the mysterious Ada Wong ends up being a recurring downfall.

When Ada first appears in "Resident Evil 2," Leon is immediately obsessed with getting to the bottom of how and why this Umbrella spy is in Raccoon City. In the tense climactic moments of the game, Annette Birkin tries to shoot Ada, but Leon takes the bullet instead. That's a pretty hardcore crush, if you are willing to give your life for someone you just met. Luckily, Ada patches Leon up and gives him a kiss, the only medicine he really needs. 

The two meet again in "Resident Evil 4," where Leon is given even more clues that he probably shouldn't trust Ada. He does anyway, which leads to the villainous Wesker getting a sample of the deadly Las Plagas parasite. By the time players reach "Resident Evil 6," it's clear Leon will go to extremes for Ada. When her life is threatened by Chris Redfield near the end of "RE6," Leon does what he must to protect her. This means getting into an over-the-top fist fight with Chris before the series' leading men finally cut it out and start acting like grown-ups.

Has a bad habit of flirting during terrifying situations

Leon's always a hero, but that doesn't mean he's always the most serious character in the series. Depending on which rendition of the Rookie Cop turned DSO operative you see, he can be quite sarcastic and flirty. 

Across the games, players consistently see Leon choosing to flirt with pretty ladies at times when he should be having more mortal concerns. In the remake of "Resident Evil 2," Leon and Claire can often be seen flirting and quipping slyly back and forth during their limited screen time together. A little chemistry between leads is fine and dandy, but when you turn around to see a horde of zombies climbing a fence and heading your way, you can't help but feel Leon should have his priorities more in order. 

Another instance of his inappropriately "friendly" behavior comes in "Resident Evil 4." In a conversation with his intel operative Ingrid Hunnigan, Leon asks her out after she removes her glasses for one call. Yes, this is the same mission where his infatuation with Ada Wong leads to further shenanigans from the Umbrella Corporation.

Looking up Ashley's skirt

Yes, if you play "Resident Evil 4" just right (or wrong), you can implicate Leon in peeping on the President's daughter. While this bit is not necessarily canon, many players have made Leon do this, either by mistake or totally on purpose. And honestly, despite his heroism, you can't deny this is pretty much in line with Leon's previous inappropriate behavior.

In "RE 4," if players aim upwards at Ashley as she is climbing a ladder, they will be able to see underneath the skirt she is wearing. When she notices, Ashley will cover herself with her hands and scold Leon, asking "Hey, what are you looking at?" Sometimes she'll even call him a pervert. 

While this little bit of anime-es1ue humor was par for the course in games in the mid-2000s, gaming audiences and developers aren't quite so keen on it now. This is evidenced by the fact that the scenes of Leon peeking at Ashley were cut from the VR version of "Resident Evil 4," released in 2021. This little bit of self-editing could mean that the upcoming remake of "Resident Evil 4" may also omit this crude aspect of the original game.

Not trusting Ben Bertolucci

While not in the original game, there is a moment in the acclaimed 2019 remake of "Resident Evil 2" where Leon Kennedy makes a huge mistake. When he reaches the jail cells in the Police Station, Leon encounters a man who is locked behind bars. This man introduces himself as Ben Bertolucci, a local journalist in Raccoon City. According to Ben, he was locked up by the Police Chief Brian Irons after he discovered some dirt on the corrupt Chief and planned to go public with it. Before the outbreak, Irons locked him in a jail cell to buy him some time. 

This is a pretty believable story, and yet Leon is hesitant to go along with it. As the conversation continues, Bertolucci begs Leon to let him out of his cell, even offering him his keycard to allow Leon to escape through the parking garage. Leon's trust in authority gets the whistleblower killed in the brutal conclusion of the scene (via YouTube), when the monstrous hand of Mr. X reaches through the wall to crush his head. Oh Leon, you were so close to saving this man. 

Not actually shooting Jason in Infinite Darkness

The Netflix 3D animated series "Resident Evil: Infinite Darkness" attempts to span some of the gap between "Resident Evil 4" and its sequel. Released in 2021, "Infinite Darkness" reunites Leon and Claire, the heroes from "Resident Evil 2," in a four-episode action romp. 

One of the new characters introduced in "Infinite Darkness" is rugged war hero Jason (voiced by Ray Chase), a brooding character whose motivations didn't make a ton of sense to fans. So in the second episode, when its revealed he is conspiring to expose the U.S. Defense Secretary for committing war crimes using bio-organic weapons (B.O.W), Leon defaults again to his trust in authority. He turns on Jason and the show sure makes it look like Leon shoots him. Oh, if only!

The truth is much worse when Jason comes back in the finale to transform into a B.O.W. himself. By not killing him when he had the chance, Leon allowed for the creation of a bio-organic monster. Ultimately, the blame for deaths caused by Jason's destructive new form lies partially with Leon.

Not allowing Claire to release the data they recovered in Infinite Darkness

Another poor judgement call from Leon comes in the closing scenes of "Infinite Darkness." The worst part of this decision is the fact that his old friend Claire Redfield is right there to tell him to do the right thing, but Leon simply doesn't listen.

At the end of "Infinite Darkness," Leon and Claire have recovered data that proves Jason's claims that Defense Secretary Wilson was involved with supplying B.O.W.s to a foreign conflict. During the final battle in the fourth episode, Wilson is infected by the B.O.W. form of Jason, but manages to escape. Claire wants to go public with this information and expose Wilson, but Leon refuses. The former cop explains that he believes that he will be able to best use the information to stop further B.O.W. outbreaks and the public doesn't need to know, because this info could destroy their faith in the country's leadership. 

Once again, it seems Leon's biggest character flaw may actually be his undying loyalty to authority figures, which he keeps intact even long after they have betrayed him. 

Leon was willing to leave Becky behind

Leon S. Kennedy finally makes his debut in the Paul W.S. Anderson's live action "Resident Evil" movies in the fifth entry, "Resident Evil: Retribution." Alongside Ada Wong (Li Bingbing) and Barry Burton (Kevin Durand), Leon (Johann Urb) is also added to the film universe in "Retribution." The three classic video game characters join Milla Jovovich's stunt-loving Alice and Jill Valentine (Sienna Guillory) for a 3D special-effects action feast. 

The plot of "Retribution" mostly concerns Alice escaping from an Umbrella facility and builds off the clone storyline started in "Extinction." Leon is working with Albert Wesker as part of a task force with Barry to rescue her, but he hints that his motivations are deeper than they seem at first glance. Unfortunately, audiences never get to know too much about this version of Leon, which is why his behavior is so frustrating. 

Alice and Ada encounter Becky (Aryana Engineer), a child clone raised by an Alice clone in the facility. Alice becomes attached to her, so when the team inevitably must destroy the facility and escape, she insists Becky not get left behind. Leon objects. 

In one of his lowest lows, Leon Kennedy argues that saving Becky is a waste of time and will jeopardize the mission. Ultimately, Leon is outvoted and reluctantly gives into helping with the proposed escape plan.