Oliver Queen’s time on CW’s Arrow series is coming to an end next season. Over the life of the series, he’s seen triumphs and failures. However, it seems more times than not the embattled hero was more accustomed to the latter never being actually capable of catching a long-lasting break. During Ollie’s experiences on Lian Yu as well as with—and without—Team Arrow, the Emerald Archer made many controversial decisions. Many of them left us, the viewers, scratching our heads. As a vigilante willing to bring pain and justice to the criminal underworld while risking life and limb, choices are an integral part of daily operations. Oliver Queen seemed to make the most unpopular decisions for better or worse.
10 Season 2 - Signing Over Queen Consolidated to Isabel Rochev
At the height of season 2, Oliver Queen was at odds with his former friend Slade Wilson. Earlier in the season, Isabel Rochev entered the scene to forcefully push Ollie out of his own company, Queen Consolidated. At every turn, she sought the opportunity to strip Ollie of his dignity as a leader by reprimanding his behavior. Later on, when Slade Wilson kidnapped Thea, and the standoff between Ollie and Deathstroke was intensified, he flippantly signed the company over to Rochev on a temporary basis so that he could focus on the task at hand. However, she took this power and called on the board to make her appointment permanent with the intent to mass-produce Mirakuru to build Slade's army. Oliver typically vets a person before he begins to trust them, but, despite Isabel Rochev's disdain for him, he made this confounding decision.
9 Season 7 – Not Finishing Ricardo Diaz in Prison
It’s unfathomable that Ollie did not ensure that Diaz ironically met his end in prison after the vengeful soul exclaimed that he would never die in a cell. The man has caused Ollie pain and suffering mostly by threatening the one thing Ollie values more than his crusade: his family. While imprisoned, it tore him apart to believe that Diaz could possibly find Felicity or his son. While he’s jumped on and off the boat of lethal force throughout the series, this is one instance that completely allowed it within the realm of Oliver Queen’s character. Yet, he didn’t do it. Why? The only reason I could possibly think of is simply that the writers wanted Diaz to terrorize Ollie more.
8 Season 5 - Becoming Mayor of Star City
I believe the saying is, "go big or go home." Ollie decided to go big. Although, this decision didn't seem to come at the direct result of an intense seasonal conflict like so many of his other hasty decisions. Instead, Oliver decided to run for Mayor at the end of season 4 so that he could better serve the city. That would be a fine idea if he weren't already a vigilante. Throughout season 5 and season 6, his enemies including Adrian Chase and Rodrigo Diaz, as well as the FBI, used his position as Mayor against him. Surely, he'd encounter enemies that'd have the wherewithal to determine that Oliver Queen is Green Arrow while being Mayor. Once that happened everything was surely going to be much worse for him. Becoming mayor didn't seem like the brightest idea for a vigilante with enemies.
7 Season 2 - Letting Ivo Control the Story of Shado's Death
We all know that Oliver never chose between Shado or Sara. Ivo orchestrated that choice by pointing the gun at Sara forcing Oliver to defend her. The way in which this was revealed to Slade could have possibly been written differently. But in the way it stands now, Oliver had Ivo dead to rights. Yet, in typical stupid-movie-and-tv-show-decisions fashion, he let Ivo keep talking.
When Slade entered the room, Oliver stood by as Ivo manipulated the conversation, making it seem as if it was Oliver's fault that Shado was killed. Ivo stated he was angry and told Oliver to choose between Sara and Shado, and that Oliver chose Sara. When Slade asked Oliver it was true, Oliver could barely utter a competent explanation for the clear villainy afoot. Granted, this set the stage for the entire conflict of season 2. So, it had to happen, but this false revelation shouldn't have happened like this with Oliver simply being paralyzed at the moment.
6 Season 6 - Raising a Son
It's absolutely mind-boggling that Oliver ever brought a son into his world. The first few seasons of the series were all about Oliver coming to grips with the dangerous nature of his nightly duties. He kept his secret from everyone including his closest friend Laurel and his mother and sister. He pushed Felicity away from a potential relationship at one point because of the dangerous position she'd be in. Eventually, she convinces Oliver she accepted the occupational hazards regardless and they become an item.
Then Oliver's son is introduced and his mother dies as a result of the enemies Oliver has made. What's the best thing for William? Of course, bring him into Oliver's life with a bedroom just down the hall. If Oliver was going to be the dad he vowed to be, he would've given up his crusade. But then, the show would've ended. So he most certainly should have found a way to keep William safe at a distance, even if that meant sending him to live with grandma or Uncle Bob on his mother's side. Hell, send him away with Thea and Roy. He'd be safer there than being threatened by monsters like Diaz.
5 Season 4 - Not Telling Felicity He Had a Son
There really was no valid reason at all for Oliver to keep this a secret from Felicity. "You are the only person on this planet who considers the truth complicated," Felicity says. I don't think we could agree with her more. At this point, Ollie is four seasons into his crusade. If he's learned even one thing, it's that his secrets sow division between him and his allies. While smartly keeping secrets from enemies and the general public may be one thing, compartmentalizing information from his own team members and love interests will always spell disaster in the end. For those who haven't watched beyond season 4—spoilers—Oliver still hasn't learned this lesson.
4 Season 5 - Paying a Mob to Kill Adrian Chase with Stolen Medicine
That's right. That's something Oliver Queen actually did. It kind of goes against every fiber of his character as established by the writers of the show for 4 seasons previously. Ollie resorted to bringing the Bratva into his conflict with Adrian Chase in order to end him. In exchange, he pledged to turn the other way while the Bratva stole medicine. One could argue that Oliver made this choice out of desperation. However, it's hard to perceive Adrian Chase as a greater threat than any of Green Arrow's past enemies. Oliver just has more to lose being the mayor. But now, at this moment, he allowed himself to become corrupt. Oliver was quickly convinced to reject this plan and come to his senses. In doing so, he betrayed his deal with the Bratva and created an all-new enemy. The leader of the Bratva and Ollie's former friend, Anatoly Kynazev, would go on to cause trouble for Team Arrow.
3 Season 6 - Constructing a Team, Destructing a Team
It was clear that Oliver wanted some help on the streets of Star City, even if he wouldn't admit it. After building a team with Mr. Terrific, Wild Dog, Ragman, and the new and improved Black Canary, Oliver later threw it all away by acting like a petulant leader with a "my way or the highway" mentality. The classic Team Arrow worked like a well-oiled machine because it was the sum of everyone's parts instead of robots that followed Ollie's every command. It seems that Ollie should have learned this with the struggles of his former team, but the dissolution of the new Team Arrow proved that he didn't.
2 Season 3 - The Entire Covert Plot
Season 3 was undoubtedly a disastrous affair, but nothing was quite as bad as the season's final moments where Oliver decides to "give in" to the demands of the League of Assassins. Ra's Al Ghul's primary demand, of course, was that Oliver marries his daughter Nyssa and take his place as the Demon's Head in charge of the entire murderous crew. This all seemed like a contrived means of manufacturing character drama between Ollie and his team as well as building to some big finish with the finale. However, nothing that the forces of good accomplished—miraculously—in Starling City was something that couldn't be accomplished with a well-executed plan outside of Queen's covert operation. Despite the plan, why couldn't Ollie clue his team into his entire turncoat scheme?
1 Season 1 - Not Trusting An Old Friend
Oliver became the ultimate hypocrite in season 1 when he withheld the fact that he was the vigilante from his closest friend, Tommy Merlyn. Eventually, he revealed this fact to his best friend, but due to the late timing of the truth, it shook their relationship. Nevertheless, Tommy kept and protected Oliver's secret. In fact, Oliver would go on to prove at times that he wasn't entirely trustworthy and would keep countless secrets throughout the course of his vigilante life. But, Oliver did not reciprocate the trust back to his closest friend. While Tommy was a bit of a party boy, he began to mature when he left the ATM machine that was his father. He got a real job from Oliver as a club manager at Verdant—a club owned by Oliver. But, after evidence suggested that he was dealing drugs, Tommy insisted with Oliver that he wasn't the culprit. However, Oliver didn't trust him. Later, Tommy's name was cleared. But, that shattered their friendship and Tommy quit his job.