12 Times Tony Stark Was Outsmarted In The MCU

It's fair to say Tony Stark had a weakness for women. Nick Fury, a genius spymaster, used this weakness to his advantage by having one of his agents infiltrate Stark's inner circle by posing as an assistant. Fury knew that just by nature of getting the Black Widow, AKA Natasha Romanoff, in front of Stark, that he would ask her to be his assistant

The plan worked perfectly, and Stark, known for underestimating those around him, didn't suspect a thing. 

After Baron Helmut Zemo lost a lot of loved ones during the Avengers' time in Sokovia, he spent his life attempting to take down the so-called heroes. Zemo was something of a genius and knew that if he wanted to get rid of the Avengers, he would have to convince them to get rid of each other. 

Zemo went after the Avengers' weakest link by framing the mysterious Winter Soldier for the death of King T'Chaka. The Winter Soldier, a former assassin, wasn't believable as the killer of a king, and Iron Man and Captain America were split on whether or not they should turn him in. 

The feud eventually climaxed with Zemo showing Tony Stark that the Winter Soldier did, in fact, take the lives of Stark's parents. This reveal effectively ended the Avengers for a couple of years until Thanos went after Earth, which forced the group to reconvene. Zemo outsmarted Stark by using his own emotions against him. 

Ultron, created by Bruce Banner and Tony Stark, was smarter than the sum of his creators. When Stark made Ultron, he attempted to play God, thinking an AI peacekeeping force would be best for humanity. But Stark was blinded by his own ego and created a monster he could not control. 

Upon awakening, Ultron quickly brought down JARVIS, the less-sophisticated AI tasked with babysitting him. Ultron was also intelligent enough to grab Loki's scepter, a device key to his creation. 

Tony Stark ultimately outsmarted Obadiah Stane, but that victory didn't come without a few bumps on the road. 

Stane took over Stark Industries as an interim CEO after Howard Stark's passing, before Tony was old enough to take over for his father. Stane decided he didn't want to give up control of the company, so he attempted to have Stark eliminated by an extremist group called the Ten Rings. His plot failed, and Stark recovered, returned, and built an arc reactor to keep his heart going. Stane decided that reactor would be great for earning some cash and upping the company's stock prices, so he used a short-term paralyzer to stun Stark and remove the arc reactor from his chest. This outsmarting was a bit of a long con because Stark had no reason to believe he couldn't trust Stane. 

Tony Stark was kind enough to take a mentor role in the life of Peter Parker. As part of this role, Stark got Parker involved in a superhero civil conflict and gave the teen a high-tech Spidey suit. This suit came with a tracker and training-wheels protocol that kept Parker from harming himself or doing anything Stark didn't want him to. 

Stark apparently underestimated a high schooler's ability to understand his technology, because Peter (alongside his best friend and man-in-the-chair, Ned) had no trouble hacking into the suit to disable the protocol and remove the tracking chip. Another classic instance of Stark underestimating those around him. 

Add Maya Hansen to the ongoing (well, not ongoing after Endgame) list of people Tony Stark wronged. She was a promising scientist who wanted Stark's help with a project, but instead, he had a one-night stand with her and left in the morning. This act sent Hansen into the open arms of Aldrich Killian and his think tank AIM. 

Hansen popped up in Stark's life later on, apparently to warn him, but she was really manipulating events to force him to help her. Hansen absconded with Pepper to use as leverage to get Stark to help her fix Extremis.