Determined to stand for all that is valiant and good, Steve Rogers, a.k.a. Captain America, the patriotic super soldier, has faced countless threats since punching his way onto comic book pages back in 1941. He has repeatedly stood in the way of enemies who have threatened freedoms, confronting bullies of all shapes and sizes from all across the galaxy.

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With nearly 80 years of comic history behind him, he’s built up quite a cast of villains determined to see him–and Earth–fall. Looking through the countless characters who have attempted to take down the man behind the shield, here are the 10 worst villains that Steve Rogers has ever faced.

10 Batroc The Leaper

French kickboxer Georges Batroc may seem silly rather than a sincere threat, but he has proved to be a regular thorn in Cap’s side for decades. A man who likes to describe himself as the world’s greatest mercenary, he mastered Savate during his time in the French Foreign Legion, becoming a formidable and determined fighter.

A master of deception and military tactics–often combining the two to outsmart his enemies–he once led his own motley crew of criminals, named Batroc’s Brigade. Often found to be working for Red Skull and Hydra, the martial arts extraordinaire would rank higher on the list if he hadn’t been thwarted by Cap and the Avengers so frequently.

9 Arnim Zola

Behind every evil figurehead is a genius so diabolical (and slightly unhinged) that his creations become the real threat. Swiss geneticist Arnim Zola was a valued member of the Third Reich, often involved in experimenting with artificial life in the late 1930s and providing the Nazis and Hydra with experimental weaponry. Consumed by this passion for “Deviant science,” Zola built himself a new robotic body whose design could only come from the brilliant mind of Jack Kirby.

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The scientist’s brain was protected inside his chest, covered by a holographic face. Some of Zola’s notorious experiments include resurrecting Red Skull into Cap’s cloned body, turning Cap into a werewolf for eight whole issues and preserving Hitler’s consciousness so he could live on, creating Hate-Monger.

8 Crossbones

Brock Rumlow was destined for villainy before he even acquired his super-villain name. As a teenager, he ran the Savage Crime gang, which terrorized the streets of New York. He was forced to flee after murdering a young boy (later revealed to be Rachel Leighton, a.k.a. Diamonback’s, brother). Training to become a mercenary under Taskmaster, he proved himself to be a skilled fighter and quickly formed his own team, called the Skeleton Crew.

Working alongside Red Skull and Hydra, he has battled Cap numerous times over the years, and has even led a branch of A.I.M. But his most devious deed came at the end of Civil War, as he fired a shot into Cap’s shoulder which would cause a distraction allowing mind-controlled Sharon Carter to kill Steve Rogers.

7 Sin

The daughter of Red Skull, Sin (or Sinthea Shmidt) was raised by the nefarious Mother Superior until her early teen years, where her father bestowed a number of superpowers upon her (and a handful of other orphaned girls). This chapter of Sin’s evil deeds was quickly thwarted by Cap as he reversed the effects and removed the girls’ powers, but she would get another shot at becoming a suitable heir to her father.

Training under Crossbones, she became one of the world’s most deadly assassins, skilled in espionage. Determined to do what her father never could, she once teamed up with Baron Zemo to find the Hammer of Skadi, planning to unleash the Serpent God of Fear and rule the world, leading a Nazi army into Washington. Her plans didn’t quite come to pass, however, as a Mjolnir-wielding Cap swooped in to defeat her. Sin continues to try to best her father’s legacy, even becoming the Red Skull for a brief period of time.

6 The Winter Soldier

Fighting enemies is hard enough, but fighting long-lost friends is even worse. Cap believed his best friend, James Buchanan “Bucky” Barnes, fell to his death during World War II and spent decades struggling with the loss of his friend. In actuality, Bucky was found in the icy waters by a Soviet submarine and taken to Moscow. Waking with no memories and a bionic arm, he was used by the Soviets, brainwashed into becoming a cold, efficient assassin and spy called the Winter Soldier.

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This new Bucky had impressive strength and showed no remorse when killing his targets. Contrary to the days where he served alongside Cap, the Winter Soldier wielded guns and was an excellent sharpshooter. He has fought many superheroes and won, standing toe-to-toe with Iron Man and Wolverine. Ultimately, he was one of Cap’s most fearsome foes as he not only challenged his physical strength, but his heart and values too.

5 Madam Hydra/Viper

Perhaps the most cold-hearted villain to ever face Captain America, Madam Hydra began her career of terror – as her name suggests – as a member of Hydra. After the group was infiltrated and destroyed by S.H.I.E.L.D., Madam Hydra tracked down splinter groups still loyal to Hydra and rebuilt the group’s foundations. Believed dead following a battle with Cap, she resurfaced in Virginia where she killed Jordan Stryke, the original Viper, and assumed his villainous identity, taking command of the Serpent Society.

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Highly skilled in creating fear and panic, she used her position as leader to mold the Serpent Society into a more fearsome criminal organization than ever. Cap has stalled her plans to poison Washington D.C.’s water supply and even stopped an assassination attempt on the President. However, her cunning mind, ruthless attitude, aptitude for leadership, and unflinching loyalty to Hydra means Viper remains one of Steve Roger’s most evil foes.

4 Baron Zemo

A father/son duo, both versions of Baron Zemo have given Cap problems since World War II. Baron Heinrich Zemo was a Nazi scientist who developed superweapons, including a huge vat of superglue named Adhesive X. His invention was to become his own enemy, however, as an accident led him to affixing his hood to his face, eventually driving him insane. Founding the Masters of Evil, Baron Zemo became such a notorious field agent for the Third Reich that he developed a rivalry with Red Skull, who feared his position was at risk.

It was this rivalry that led Zemo to England to steal a plane, with Cap and Bucky in pursuit. Baron Zemo captured the pair and tied them to the bobby-trapped aircraft, sending them to their deaths – it would be years before Cap reanimated after being frozen in ice and Bucky resurfaced as the Winter Soldier. Scarred by Adhesive X, Baron Helmut Zemo would later don the hood in honor of his father, but eventually transitioned into a hero, leading the Thunderbolts.

3 Hydra Cap

For some, there is no greater enemy than yourself. In 2017’s controversial "Secret Empire" event, readers would question everything they thought they knew about Steve Rogers. The Cosmic Cube altered history, introducing a Captain America who fought for Hydra and tyranny instead of America and freedom – and who held the power of the Cosmic Cube itself.

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Leading the fascist group after overthrowing Red Skull in a cold, back-handed attack, Hydra Cap was the self-appointed Supreme Leader of Hydra Nation. Leading America into a dark period of history with no view of hope, the original Steve Rogers eventually returned to battle himself. With powers and skills equally matched, it was a long and difficult battle, but nothing can defeat Steve’s honor.

2 Red Skull

Not only one of Captain America’s most dangerous villains, but one of the most evil minds in the entire Marvel universe, Red Skull has battled Cap since 1941, both appearing in Timely Comics Captain America #1. Originally an ordinary man named Johann Schmidt, he came face to face with Hitler himself while working as a bellboy in a hotel. The dictator recognized the hatred inside Schmidt’s heart and took him under his wing with a view to create “the perfect Nazi.”

Mentored by Hitler, who gifted him with the Red Skull mask, he quickly rose to be one of the most influential leaders in the Third Reich, growing so powerful that even Hitler feared him. Captain America has repeatedly stopped his plans for global domination, becoming his greatest foe. Red Skull grew to hate Cap so strongly that he would even execute impersonators. Appearing to be immortal, it’s likely Red Skull will prove to cause trouble for Cap and his team for years to come.

1 Hitler

When it comes to ranking Captain America villains, it’s difficult to imagine who could be worse than Red Skull himself. But there is one clear answer: the monster that created the Red Skull, Adolf Hitler himself. The cover of Timely Comics Captain America #1 is a well-known image across the globe, with the Cap triumphantly clocking the dictator on the jaw.

In the world of Marvel Comics, Hitler continued to live on until the early 2000s, in two super-human bodies created by Arnim Zola: Nazi-X and Hate-Monger.  While he may not have been the most difficult villain to defeat, his ideology and deep-seated evil makes him the worst villain Steve Rogers has ever faced.

NEXT: Iron Man Villains Ranked: The 10 Worst Tony Stark Ever Faced