Summary
Wolverineisone of the most iconic superheroes of all time. Although Hugh Jackman does a fine job playing this nearly indestructible mutant, his character diverts pretty much from what is seen in the comics.
In fact, Wolverine has messed up more than once throughout his career as an X-Men and freelancer. This topic will cover several of the dumbest things James Howlet has done in his long life. Included are blunders from both the current canon and alternative character versions from different timelines/earths.

1The Jean Grey/Scott Summers Love Triangle
One Of His Worst Ideas Ever
During the Krakoa Era of the X-Men, and after several reboots, fans finally saw Wolverine and Scott Summers make peace, but, as some insightful readers have unveiled, it is more than that. Seems to be like Wolverine, Jean Grey, and Cyclops are now in some sort of weird love triangle: a very bad idea.
Among all the things thatcould worsen their relationship, and potentially ruin the X-Men, this is one of the worst. Wolverine has made a long list of angry ex-lovers willing to stab him in the back without notice, but this is a recipe for disaster. Just thinking about all the problems these three X-Men had due to a toxic love triangle, and the results on the horizon are not promising.

2Rejecting (And Even Killing) His Many Sons
Worst Parent Ever, By Far
Wolverine had many lovers and also had many offspring. Most of them were left behindwithout him even knowing about their existence. Harsh as it might sound, Logan is not good father material, and he proved it on several occasions. The worst was during the Earth-616 continuity when facing the Mongrels, a group of his forsaken children trained by The Red Hand to kill Logan.
Of course, Wolverine ended up killing them all, only to later find out they were his children. But throughout his career, James Howlet has proven to be a really poor parent, killing Daken (the child he had with his wife Itsu) just to later break down and hug his corpse, regretting not being able to be there for him.

3Trusting Sabertooth (More Than Once)
Fool Me Once, Shame On You, Fool Me Twice…
On multiple occasions throughout their long and tortuous relationship,Wolverine and Sabertooth had to work together, and most of the time this ended poorly, especially for Logan. During Neal Adams' and Christos Gage’s run, calledThe First X-Men(Published in 2012) Wolverine and Sabertooth can be seen leading a team of proto X-Men.
Needless to say, this ended up poorly, and both of them fought. And it wasn’t the first nor the last time that Wolverine would expose his neck to his primal half-brother (or father). They have a pretty complex and poor relationship, and the worst part is that Sabertooth is the person who knows Logan the most, so he knows how to hurt him badly.

Man Made Of Metal Challenges Human Magnet…
One of the most powerful mutants in theX-Menuniverse, with the power to control metal and magnetism at its will, Magneto is classified as Level Omega. What made Wolverine think that he, with his Adamantium skeleton, would be able to face his natural counter?
As the X-Men confronted the Master of Magnetism on his space station, Wolverine confronted Magneto. Magneto then proceeded to swat him like a fly and teach him a lesson he would never forget, by ripping apart all the Adamantium on his body at a molecular level, nearly dissolving Logan into a mush of flesh. If not for Charles Xavier and Jean Grey, he would have lost his mind due to this horrific experience.

5Challenging The Hulk
A Battle Between Two Immortals Caused Hundreds Of Casualties
If something has been made clear in each encounter Wolverine has ever had with The Hulk, it’s that the Emerald Giant does not care for collateral damage. Through the many face-offs these two immortals had, Hulk hasdestroyed countless buildings and citiesand, in one case, killed hundreds of innocent people during a traffic jam caused by these two going berserk.
The casualties had dire consequences for the Hulk, but some of them even contributed to engrossing the long list of enemies that Wolverine had been accumulating through the years. So, facing it alone without any kind of contingency plan has proven to be a poor decision for Logan.

6Unleashing The Fastball Special On Several Indestructible Beings
Didn’t Work As Intended…
Every fan of Wolverine knows about the Fastball Special, the signature move that Logan and Piotr Rasputin created to beat the toughest opponents. And even though this is a powerful move, it is practically a suicide attack. This was proven on several occasions when Colossus and Wolverine decided to launch such an attack on really powerful beings when outmatched.
The worst of them all happened against none other than Dracula, the Lord of Vampires, where Colossus and Wolverine attempted that last-minute power move to defeat the ancient vampire. Of course, Dracula shrugged it off like it was nothing, and Wolverine ended up biting grass like a fool.

7Tried To Murder Scott Summers
Went Off The Deep End Here
After a fight between Logan and Scott escalates, Charles Xavier has the brilliant idea to designate them both for a co-op mission on a desolate region of the Savage Land. The leader of the X-Menexpected that collaborating would heal the old wounds and help them make peace. But as Scott Summers slipped near a cliff and was holding on for dear life, Wolverine thought, “Here’s my chance to get Jean for myself once and for all.”
Wolverine did not whisper “Long live the King,” buthe let Scott fall to his deathand returned to the X-Academy without Cyclops, much to the shock of the rest of the team. Later, during the “Return of the King” issue, Scott reveals himself as alive and well. Magneto saved Scott’s Life after he detected him in the Savage Lands, barely surviving on insects and rainwater. Then the second plot twist: Cyclops beats the stuffing out of Wolverine and kicks him out of the team, for good!

8Tried To Make A Move On Mary Jane Watson (On Many Occasions)
Logan At His Lowest
After several attempts to conquer Mary Jane Watson (Earth 616) Logan kept pursuing her, even knowingshe was the wife of Peter Parker(aka Spiderman), and if fans thought this was a foul move on his behalf, they’d be surprised. This was not even the first time that Wolverine relinquished his decision-making to his second brain.
The worst part is that after Peter’s death during his fight against Morlun in the hospital room where he was bedridden, Mary Jane was crying her eyes out, and Logan had no better idea than to try to make a move on her. She slapped him, of course, and when Jarvis approached Logan and asked why, he said that he was trying to make MJ hit him so she could overcome her grief. Of course, no one believes that excuse.

They Never Made Up After This
Perhaps the dumbest thing Logan ever did was betray Captain America during WW2. After chasing down Baron Von Strucker and his Hydra cell, Wolverine is suddenly contacted by his mysterious contractors and revealed as a double agent. To the shock of the audience, Wolverine betrays Cap and his crew and hands him over on a silver platter to the evil guys.
Of course, it was later revealed that the one pulling the strings was Romulus, one of the oldest and most dangerous mutants in the world, but that is no excuse for such a foolish and cowardly act of treason. The worst part was that Steve Rogers even respected James Howlett and had begun to think of him as a friend.