Even though Picard is one of the most beloved Star Trek characters of all time, that has never made him a perfect man. Over his decades as a leader, he's made many mistakes that have cost relationships, allegiances, and even lives. With as many victories and triumphs as the man has had, he's also had quite a few terrible, traumatic mistakes.
Considering his life from Picard to his Starfleet days, there's a lot to think about. Of course, there would be a few haunting memories that never leave him (and no, it's not all about Data. But that would be a meme of a list, wouldn't it?). Here are Picard's 10 biggest mistakes.
Failing the Stargazer
A moment that haunts Picard was losing his first ship, the Stargazer. In the Maxia Zeta system, his ship was attacked by an unknown vessel (eventually discovered to be Ferengi). Though they destroyed the ship using the Picard Maneuver to confuse the enemy, the Stargazer was still unable to stop the fire engulfing every deck. Picard ordered everyone to abandon ship.
Losing a ship is grounds for a court-martial and Picard went through an arduous trial before being absolved. However, absolvement didn't wash away the guilt. If Picard could go back, he'd do anything in his power to save his ship.
The War Crimes of Locutus
Even though Picard had no control over his body, the events of Wolf 359 were one of the worst things to ever happen to him and The Federation. Though he has to be thankful for people saving him, there has to be apart of him that thinks saving his life was a mistake. The Enterprise should have decided on destroying him much quicker.
This is one of those mistakes that Picard didn't control, and blaming him would be victim-blaming. However, if someone asked Picard himself? His time as a Borg is still something he struggles to cope with and wishes he could make sure never happened.
Failing His Friends After Romulus Fell
After his Romulan rescue plans fell through, Picard didn't put the pieces back together and keep fighting like he used to do. Feeling defeated, and like Starfleet betrayed him and the Romulan people, Picard secluded himself in his family Chateau. He didn't contact his old associates and he didn't go back to check on the Romulans he was helping. Picard was so disappointed that he dropped everything.
And then he spent the next decade or so holed up, writing books and avoiding everyone, losing himself in his own frustration. Looking back on that now, Picard probably wishes he didn't turn his back on everyone.
Going to Edo Unprepared
Most of the time, Picard made a rule of being as prepared whenever he went down onto a planet. If that doesn't happen, it's normally because it's a high-stress situation.
Well, that is unless that planet is Edo.
Going down to Edo, Picard brought the crew because it was supposed to be relaxing and peaceful. He even brought the teenage boy. However, he didn't know anything about the laws there and therefore just by falling on some forbidden patches of grass, Wesley was sentenced to execution.
Picard likely wished he learned more about their justice system beforehand instead of having to botch a first contact situation.
Reassembling B-4
Data's elder brothers have never had a great track record of behaving well among others. Just from their dealings with Lore alone, the Enterprise probably should have done a complete scrubbing of his matrices to make sure nothing was hidden. If they had, they would have found hidden Romulan technology.
Instead, they rebooted B-4 as soon as possible without nearly enough testing, and the less advanced prototype became an unwitting and helpless spy for Shinzon.
Maybe things could have gone differently if Shinzon hadn't started out with an upper hand on Picard and the Enterprise.
Mediating Klingon Government
The Federation tries to avoid involving themselves too much in other governmental issues, at least in theory. Goodness knows that they do it all the time anyway. However, Picard possibly took it a step too far by being a mediator in choosing the next Klingon Chancellor as K'mpec's reign was ending. Assisting K'mpec left Picard and his crew embroiled in Klingon politics for the next few decades.
While they would've probably gotten involved in some way, Picard must've regretted getting so deep in the whole system. It caused a lot of chaos in the Klingon High Council, choosing a human to mediate. At least Duras didn't end up Chancellor.
Making A Teen Ensign
During his time on the Enterprise, Wesley Crusher really blossomed as a brilliant young engineer. However, his maturity didn't grow with his intelligence. People kept giving him more praise and responsibility without having him learn any of the humility and wisdom that should come with it. It's no wonder he ended up dropping out of Starfleet.
If anyone should take the blame for setting Wesley on that path, it's Picard. All it took was some prompting from a space-alien for Picard to give Wesley a position he did not earn: acting ensign on the bridge. There were probably hundreds, if not thousands, of fully-trained Starfleet cadets that would sell a lung for the role, and Crusher just got it on an order.
Giving The Crystalline Entity Any Chances
When the Enterprise first faced off against the Crystalline Entity, it was when it was using Lore as it's food ticket. He would signal it, and then it would eat all the humans. More or less, at least.
After Lore attempted to feed the Enterprise to the Crystalline Entity, they let it retreat into space, thinking they'd never see it again. Unfortunately, they didn't. It came back and devoured a few members of a human colony. They initially tried to scare the thing off again, but Doctor Marr found a frequency that hurt it and destroyed the entity.
Retrospectively, knowing how many people it ate in between meetings, Picard likely wished they hadn't let it go free.
Intriguing Q
One of the largest thorns in Picard's side for his entire life on the Enterprise was Q, an omnipotent, god-like alien that, at first, came to judge humanity. Fascinated with Picard, though, he kept coming back over and over. He tried to steal Commander Riker, he did steal Picard's girlfriend, he made the Borg aware of humanity, and he meddled with time to play with Picard.
Let's just say, no matter how much fun he was to watch on screen, he was most likely miserable to deal with in person.
Picard probably wishes he gave a less rousing and inspiring speech at Farpoint; enough to get Q off their backs, but not enough to make Q follow him forever.
His Broken Relationship With Robert
Picard had a lot of close relationships on the Enterprise, but that's not what his family life was like. His only living family was his brother Robert, who ran the family vineyard. Between Picard's accolades and abandonment, he wasn't a huge fan of the famed Starfleet captain. Even less so when his own son started being fascinated by the stars.
It took the Borg violating his brain and body to even get them on decent speaking terms again.
Hopefully, their relationship got better in their later years. However, Picard most likely regrets never being a good brother to Robert.