Vs. Captain America (Captain America #147, 1972)
Like Spider-Man, Steve Rogers has super-strength, making him more than a match for any non-super-powered human. And yet, when he and the Falcon discovered that Wilson Fisk had taken control of Hydra in Captain America #147, written by Gary Friedrich and penciled by Sal Buscema, Cap found himself barely hanging on in a fight against the Kingpin.
Buscema is at the height of his powers illustrating the battle between the two titans, cramming the combatants into tight panels to emphasize the brutality of their brawl. Cap leaps out of the way of a rampaging Fisk, who obliterates the wall in front of him. Before Steve can even center himself, Fisk hurls him across the room and grabs a pole to finish the job. Despite a well-placed kick, Cap can’t get away from Kingpin, who begins to squeeze the life out of the Sentinel of Liberty… until Falcon distracts Fisk with his bird Red Wing, allowing Steve to get away.
Vs. Daredevil, Round One (Daredevil #171, 1981)
These days, most people know Kingpin as the arch-enemy of Daredevil. It’s a well-earned designation, as Fisk has done more to ruin Matt Murdock than any other superhero. Yet, the two didn’t cross paths until more than a decade after Kingpin’s debut, finally meeting in Frank Miller‘s Daredevil #171. For the first two-thirds of the issue, Matt’s undercover as “Shades” (apparently he’s a man without creativity), a thug looking to join Kingpin’s crew. But when Fisk threatens to catch Shades rummaging around secret files, Matt switches to his familiar diabolical duds and the fight is on.
At first, it looks like Daredevil will easily outclass his opponent. The first page and a half of the fight consists of nothing but Daredevil getting in his blows and then leaping away before Fisk can land a counter-attack. But when Wilson does finally deliver a punch, it’s all over for DD. Unlike most of the entries on this list, Fisk wins the bout, and only delegates the job of killing Daredevil because he must quickly pay a ransom and free his beloved wife Vanessa. Fisk’s underlings don’t do the job right and Matt gets away, leading to many, many more fights between Daredevil and the Kingpin.
Vs. the Red Skull (Captain America #378, 1990)
Midway through his legendary decade-long run on Captain America, writer Mark Gruenwald had super soldier Steve Rogers join the war on drugs. The “Streets of Poison” arc does contain some of the reactionary politics that you might expect, but it also includes some incredible moments, such as Cap getting doused with cocaine, pretending to be the Punisher, and pummeling Daredevil. But one of the most memorable moments comes when Wilson Fisk and the Red Skull fight it out. After stripping down to their underwear, of course.
Penciler Ron Lim has a blast staging the fight scene, making Red Skull every bit the sniveling weasel that he is while portraying Fisk as a human brick wall. As in most of his grudge matches, Fisk has trouble keeping pace with his adversary. And even though his punches threaten to level the Skull, he never lands them clean enough to knock the Nazi out. Out of ideas, Fisk plays the one card he has left, flopping on top of Red Skull and refusing to move until the fascist yields.
