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In the first chapter, Matthew gives the Genealogy of Jesus. In contrast to common practice of the time, he goes out of his way to include five women in this timeline.?—?There are at least 40 other great grandmothers he didn’t mention. It was highly unusual to mention a woman at all. And the ones he chose, most would want to hide, but he chose to Highlight them.
Who are these Grammy Award winning Grammy’s of Jesus?
Tamar, Rahab, Ruth, Bathsheba, and of course Mary.
I mean, at first glance, he picked four of the all-time losers, two prostitutes, an adulteress, and an outcast, Gentile. 
He picked Tamar, whose story would make a black mark on a piece of coal. 
He picked Rahab who was a professional prostitute. 
He picked Ruth, whose ancestry had its origin in the incest
And he picked Bathsheba, some say was an adulterous, I’m not sure she had choice, but she suffered great heartache and shame nonetheless.  
And those are the four women.The GREAT GLORIOUS GRANDMOTHERS OF JESUS ancestry.com commercial
Of all the women that could have been put in the genealogy, he put those four in there.  Why would Matthew do that? .I think he smiled as he wrote it.  I think it was just an amazing thing to say to those Jews while he's giving them this legal line...he just scatters a few prostitutes and adulteresses and Gentiles.  What's he doing that for?
He's doing that to demonstrate that in the midst of the law there is what? There is grace. And he's giving them a case for grace, is what he's doing. This introduces the law-loving Jews to the reality of divine grace; that even outsiders, and outcasts are included in the the line of the Messiah. And today it’s so that you and I can know that although their choices to leave their past behind came at a great COST, their choices were rewarded with generations of blessings.