Gregory was born in 1573, toward the end of the 16th century, to a poor family. they stole money and food to survive. as one of the criminal poor, if he was ever caught he wouldn't be subject to the punishments that were provided to the rich that were mostly exile and banishment. as time moves on gregory has kids and grandkids and the tradition of stealing to survive continued. what was the most likely punishment during that time if gregory did get caught stealing?

The answer would be Hard Labor.

The words 'Hard Labour' describes the punishment exactly. Prisoners were often used as the main work force in quarrying, building roads or labouring on the docks. There were several reasons. Firstly, it was felt that it would teach prisoners the value of hard work; secondly, it would remove the temptation for idle men get up to mischief and thirdly,it would deter others from committing crime.  

Most likely Gregory would have been imprisoned. During this time, prisoners were given bread and water. They were made to pay fines and if they could not pay the fines their sentence was turned into hard labor. If someone was unable to pay the fines or do labor, they were subject to the death penalty. If he were to get caught stealing from a church, he would immediatly receive the death penalty. In some cases, people were banished or deported for stealing instead of being imprisoned.  

it´s related to his charming character.

beauty is not everything, although we can joke that girls only care about the physical or material aspect, the truth is that a real woman looks at more important things, besides intelligence and personality, there are other attitudes that make irresistible to men who are 'unattractive'.

for example develop your sense of humor.