Myles Coverdale, one of the earliest translators of the English Bible gave a very powerful principle for understanding the Bible that has immensely helped me to understand very difficult passages of the Scriptures. Below is what he said.
“It shall greatly help ye to understand the Scriptures if thou mark not only what is spoken or written, but of whom and to whom, with what words, at what time, where, to what intent, with what circumstances, considering what goeth before and what followeth after.”
With this guide above, let’s take a closer look at Matthew 6:14-15 and discover why Jesus said what He did in those verses.
(Mat 6:14)  For if ye forgive men their trespasses, your heavenly Father will also forgive you:
(Mat 6:15)  But if ye forgive not men their trespasses, neither will your Father forgive your trespasses.
Two things that calls for our attention when it comes to understanding the verses we just read are:
1. The audience to whom those statements were made and
2. The Time it was made.
Regarding His audience, we know from those passages He was talking to His fellow Jews, people who had all their lives believed in a system of do good get good, do bad get bad (the Law). It was under this dispensation (time) of the Law that Jesus was born.
(Gal 4:4)  But when the fulness of the time was come, God sent forth his Son, made of a woman, made under the law,
(Gal 4:5)  To redeem them that were under the law, that we might receive the adoption of sons.
Made under that system of the Law and speaking to people who held strongly to it, there were times Jesus did and said things according to their beliefs to magnify and expose the weakness of man to be justified before God based on his own efforts which the Law required.
He magnified and stretched that system of beliefs so the Jews could see their inadequacies and their need for a Saviour. Having nothing of themselves to boast of except the mercies of God.
(Rom 3:19)  Now we know that what things soever the law saith, it saith to them who are under the law: that every mouth may be stopped, and all the world may become guilty before God.
(Rom 3:20)  Therefore by the deeds of the law there shall no flesh be justified in his sight: for by the law is the knowledge of sin.
So He encouraged them to strive to gain God’s forgiveness based on how they themselves have been able to forgive others, a feat that is practically impossible for any man to achieve since God’s true forgiveness can only be received by faith alone in the sacrifice of His Son Jesus.
However the moment Jesus died for sin and resurrected gloriously, God completely forgave man all his sins based on Jesus blood that was shed for him.
(Col 1:13)  Who hath delivered us from the power of darkness, and hath translated us into the kingdom of his dear Son:
(Col 1:14)  In whom we have redemption through his blood, even the forgiveness of sins:
(Col 2:13)  And you, being dead in your sins and the uncircumcision of your flesh, hath he quickened together with him, having forgiven you all trespasses;
Having ushered in a New Covenant and taken the first step to forgive us all our sins, God then invites us to imitate Him and reciprocate the same to all who offends us.
(Eph 4:32)  And be ye kind one to another, tenderhearted, forgiving one another, even as God for Christ's sake hath forgiven you.
(Col 3:13)  Forbearing one another, and forgiving one another, if any man have a quarrel against any: even as Christ forgave you, so also do ye.
In the same way He forgave us without waiting for us to ask, cry or even feel remorseful for our sins, we are also to forgive others without any form of condition attached.
In extending this forgiveness towards others and walking in love always, we as Lights in the world will be shining His Light on every corner.
I hope this blesses you.
Glory to God!

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