Just felt like I'd pop in and see if I can get opinions on an OC as this group seems ideal for, starting with an OC of mine named Hoodwink. I will include artwork of him at the bottom of this post to avoid it creating an unnecessary splice in the character description.

Name: Hoodwink (Alias. Real Name: Tea Leaf)

Age: 28

Race: Earth Pony

Gender: Stallion

(A note: When Hoodwink is mentioned to have left home at age sixteen it is a decade until the return of Princess Luna, as this history begins prior to the events of the series)
History: Tea Leaf was given up for adoption almost immediately by his parents due to them not being able to support a child and wanting him to have a better life. He was adopted at the age of six by a noble family from Canterlot simply looking for a way to look good to the general public; in reality Tea Leaf was not cared for even slightly, while never abused in any direct way he was left mostly in the care of the staff who didn't particularly care for him once he started acting out as a means to get attention.

After a while of simply breaking things or getting into fights with other colts to get attention Tea Leaf found an interest in reading thanks to the butler forcing him to do his homework for once. Specifically, Tea Leaf found himself engrossed in the Daring Do stories and what for most ponies would simply be a love of adventure and fun characters became an obsession.

Tea Leaf began modelling himself after the characters in the books, taking particularly inspiration from the character of Snazzy Shades, actively building an image and persona as a suave gentlecolt thief. When he hit the age of sixteen Tea Leaf proceeded to steal everything valuable he could manage from his adoptive family and left the house under cover of night, quickly setting off to build a legacy as the greatest thief in Equestria.

Tea Leaf received a harsh awakening that being a thief was not as easy or as carefree as the books made it seem at first but while many would've folded or had their delusions shattered, Tea Leaf simply grew more determined through failures; running with actual professional criminals and through learning from his mistakes by the time he had hit the age of 22 he had grown to be a known commodity for criminals looking for a professional to "acquire" goods unavailable by conventional means, though more superstitious ponies began to turn away his service due to Hoodwink (as he was now known) also often infiltrating and plundering ancient tombs and ruins for treasures.

Hoodwink's infamy increased when he was featured in several Daring Do books, after having encountered the legendary treasure hunter in person several times. Despite their butting of heads, Daring Do and Hoodwink actually worked together more than once against Ahuizotl and other threats due to Hoodwink's greed taking priority as opposed to a desire to genuinely rule or destroy anything.

After over a decade as a free stallion and building his infamy, particularly for his numerous high profile heists against the Canterlot Nobility which were mockingly orchestrated for his own amusement more than anything, Hoodwink came up on Princess Celestia's radar due to rumors that the stallion had began to hunt for the Elements of Harmony to prove himself as the greatest thief and treasure hunter in history.

Celestia did not believe Hoodwink would be able to accquire the Elements, and even if he did they would be worthless to him, but the information intrigued her enough to look further into his case and what was known of him; seeing an opportunity, Celestia set up a sting operation for Hoodwink using false information on the Elements as bait; the stallion's ego prevented him from worrying about breaking into Canterlot Castle for a heist and he was caught by the royal guard as he broke into the room where he was informed the Elements were, along with a guardpony who had been acting as an accomplice.

After a few months left to stew in the cells, Celestia pulled Hoodwink out of his prison sentence and brought up in person his history of breaking into ruins and tombs despite the curses and traps placed upon them; seeing that he clearly had great knowledge about these civilisations and a skill for avoiding their traps and handling ancient artifacts without getting himself cursed, blown up, petrified or some other horrible fate, the princess decided to offer the stallion a deal to work for her in exchange for not having to live out his prison sentence.

It took several more months for prison to take enough of a toll on Hoodwink's ego that he would agree. He now works for Celestia as a spy and when needed an expert on ancient cultures and old forms of magic, working alongside some of Celestia's graduates from her academy on the latter subject. Despite supposedly being reformed, Celestia has made use of Hoodwink's experience and skill as a thief for a few "under the table" operations, as has Princess Luna upon her own return to Equestria.

Personality: Having modeled himself on antagonists of Daring Do and other famous thieves, it should not be surprising to learn that Hoodwink has quite an ego; even alluding to events such as his capture by Celestia or the times he failed to acquire his foal in a heist will make him irritable and likely to steer the conversation away from said events. Due to having lived by taking what he needed when he needed it without thoughts of paying for it or ownership of others, Hoodwink's kleptomania does still rear it's head and it is advisable even amongst his friends and allies to check their pockets after talking to him. Even if there is nothing of value to gain he is likely to pickpocket ponies simply to prove he can do it, or watch their reaction when they realise something is missing.

Despite these obvious character flaws, Hoodwink is not an all bad pony; he frequently would work together with Daring Do during his time as a thief whenever there was a chance of innocents dying or worse if Ahuizotl was involved and when pushed he is willing to do altruistic things on their own merit, though it will usually take the promise of some kind of long term reward. Despite his suave and charming nature (which he practiced actively in his early days), Hoodwink has little desire for romance or physical pleasures and generally keeps a small but close knit circle of allies and friends; his relationship with Princess Celestia can be strained at times as Celestia still wishes to see Hoodwink one day fully reform and even regret his past crimes but so far he shows no sign of regretting it.

While Hoodwink will happily steal from almost anyone, foals are off limits to him both for stealing from and harming in anyway. This, as well as his often childish sense of humor and immature behavior when not sustaining a polite and charming act, are speculated by Celestia to come from the fact he was never allowed a proper childhood. Despite this childishness at times, Hoodwink is very intelligent and manipulative and will often intentionally play up his ego and immaturity to make people doubt his ability to undermine them (a trait he picked up from when he used to theorise Prince Blueblood was pulling a similar act).

Skills and Specialties: Hoodwink possesses no real special abilities, and in fact the usual strength of the Earth Ponies is very much not present in him for the most part. He makes up for this by having trained himself as an exceptional acrobat, capable of agility and acrobatics comparable to that of a pegasus using their wings to assist with movement, though obviously he has far less room for movement than them.

Hoodwink has taught himself a variety of skills useful for an explorer and thief such as lock picking, tracking, brewing of potions, survival techniques and becoming multi-lingual, able to speak five different languages.

Weaknesses: Hoodwink is, frankly, an abysmal fighter. In his early days his partnerships with other criminals were more out of a need for someone to defend him if things went badly and less because he actually needed their help to steal or hunt treasure. As time has gone on he has needed these alliances less and less due to learning to talk his way out of most confrontations but still when a fight breaks out he will usually hide himself and wait for it to be over.

Appearance:

4660560 A stallion of fortune? It's pretty cool how he's got such a set of skill under his belt, even if he's got some combat flaws. My only question is...are there five languages in Equestria?

Edit: He's got a pretty slick look to him too, gr8 m8.