Andrew Winchester is a stupid person.
I call Andrew Winchester a stupid person because only an idiot would believe handing over 47 handguns, all legally purchased and registered to him, to an unlicensed individual wouldn't have severe consequences. You would think being paid $900 per purchase over and above the cost of the guns and ammunition just might be a clue something is not quite legal.
Not Andrew Winchester.
In order to work for his previous employer, Garda Security, he took the Canadian Firearms Safety Course for both non-restricted and restricted firearms. He passed the course, applied for and was issued a Canadian firearms license.
He then purchased 47 handguns over a 5-month period and re-sold them to a friend of his. His friend did not have a firearms license. Selling 47 handguns to his unlicensed friend is a criminal offense.
The Criminal Code of Canada is quite clear about the transfer of handguns or as the law refers to them, restricted firearms.
Section 23.2 (1) A person may transfer a prohibited firearm or a restricted firearm if, at the time of the transfer,
(a) the transferee holds a licence authorizing the transferee to acquire and possess that kind of firearm;
(b) the transferor has no reason to believe that the transferee is not authorized to acquire and possess that kind of firearm;
(c) the transferor informs the Registrar of the transfer;
(d) if the transferee is an individual, the transferor informs a chief firearms officer of the transfer and obtains the authorization of the chief firearms officer for the transfer;
(e) a new registration certificate for the firearm is issued in accordance with this Act; and
(f) the prescribed conditions are met.
As you can see above, Andrew Winchester broke every single part of this section of law.
From the judgment in R. v. Andrew Winchester, 2014 ONSC 2591:
 There are a number of aggravating circumstances in this case, most of which are self-evident. First, Mr. Winchester used his firearms licence to purchase and then transfer forty-three handguns to another person, his presumed friend, Nour Marakah. Second, Mr. Winchester transferred these handguns knowing that Mr. Marakah would, in turn, be providing them to another person. It must have at least crossed Mr. Winchester’s mind that these were not guns that were being acquired for lawful or innocent purposes. If that thought did not cross Mr. Winchester’s mind, it ought to have. Third, Mr. Winchester undertook these purchases with an assurance from Mr. Marakah that the firearms would not be traceable back to him. This was yet a further reason that should have caused Mr. Winchester to question what was, in reality, going on. It also should have caused him to rethink his participation in this venture.
It is unfortunate that Andrew Winchesters two sons will be without their father for the next six years (He received 2.5 years credit for time served before his trial), but such is the high price of stupidity.
Mr. Winchester is, however, fortunate Superior Court Justice Ian Nordheimer laughed at Crown's retarded argument that his lack of a prior criminal record should be viewed as an "aggravating circumstance" at sentencing.
 Finally on this point, the Crown submits that another aggravating circumstance is Mr. Winchester’s lack of a criminal record. The Crown’s reasoning is that it was the lack of a criminal record that allowed Mr. Winchester to obtain a firearms licence that in turn allowed him to purchase these handguns. I do not accept that reasoning. It is well-established that the lack of a criminal record is a mitigating factor not an aggravating one. [..] I do not know of any authority, and none was cited to me, that has ever held that in a situation, such as the one here, the lack of a criminal record can be transformed from a positive factor into a negative one.
At the end of the day, as the court judgment makes clear, Andrew Winchester had a very misplaced sense of loyalty and obligation to his high school friend Nour Marakah. That sense of loyalty and obligation cost Andrew Winchester his freedom, his fiance, his job and his sons.
I doubt Andrew Winchester views the $15,000 he received as payment for purchasing the handguns was worth it as he sits in a federal prison cell.
He would be correct.