Forgiveness as taught by Jesus — A Very Hard Teaching

Here are the main points covered in this teaching:

  1. If you repent and God forgives you, you still may be punished.
  2. If you know you’ve committed a sin against your neighbor and have not yet repented, don’t even consider entering God’s house to ask for His forgiveness of your other sins.
This first point is from the Torah and the second point is specifically from Jesus. It’s the hard one. Let’s dig into this a little deeper.
Speaking through the prophet Isaiah (Isa 55:7) God reveals that repentance followed by divine forgiveness is the centerpiece of His offer of salvation:
Let the wicked leave his way, and the man of idolatry his schemes; and let him return to the LORD; then He will have compassion on him and the LORD will forgive him.(my translation)
Forgiveness: The Classical, Torah View:
The doctrinal beliefs established during the second-temple period (Jesus lived toward the end of this period) arose from the Torah (both oral and written), the Prophets, and the Psalms.  While much disagreement existed among the two most prominent factions (Hillel and Shammai), the doctrine of forgiveness was not a matter of much controversy – except as developed by Jesus (see below).
Both schools, including Jesus, held that divine forgiveness was understood to be available for all sins except those of the defiant and unrepentant sinner (Num 15:30-31). The Scriptures reveal repeatedly that divine forgiveness is not automatic, but requires repentance. Further, collective forgiveness (e.g., the Israelites as a nation) requires atonement by sacrifice. Moreover, collective forgiveness wasn’t cult-specific, but also included all believing gentiles living among the Israelites (Lev 4:20, 26, 31, 35; Lev 5:10, 13, 16, 18; Lev 26:1) Once atonement was accomplished, the peoples’ sins were forgiven.
NB: I would also note that the Jews of Jesus’ day believed that God’s grace encompassed sins that arose out of ignorance (Num 15:25-28). Reflect on our LORD’s plea while on the cross that the Father forgive his persecutors “for they know not what they do” (Luke 23:34).
In Jesus’ day, as today, Jews believed that both collective and individual sin is forgivable . As if to emphasize the point, the Scriptures state repeatedly that on the Day of Atonement, “all the iniquities” and sins of Israel were to be requited (Lev 16:21, 30, 32, 34). Also, divine forgiveness of individual Israelites was available, but only to those who would properly “humble themselves” in true confession (Lev 16:29, 31). This is the kind of forgiveness, for example, for which Solomon prayed when he led the prayer of dedication for the Temple (1 Kings — and its parallel text in 2 Chr 6). Other examples of this kind of prayer was Amos’s request for Judah (Amos 7:2) and the prayer of Daniel (Dan 9:19).
However, divine forgiveness was not to be taken for granted. The Israelite nation was not always forgiven (Deut 29:19; Lam 3:42). Moreover, forgiveness does not preclude punishment (Exo 34:9; Num 14:19-20).
Forgiveness: Jesus’ View
When theologians speak of Jesus’ teaching, they often use the term “intensify”. This term is meant to convey the idea that Jesus’ teaching was, as often as not, more demanding of His followers than the teachings of His contemporaries. For example, while Jesus taught a conventional, Torah-based soteriology of confession, repentance, and forgiveness, He extended the teaching in a very significant way by making the process more personal and therefore much more difficult. Specifically, He taught that …
…if you bring your gift to the altar, and there remember that your brother has something against you, “leave your gift there before the altar, and go your way. First be reconciled to your brother, and then come and offer your gift. (Matt 5:23-24)
In other words, Jesus teaches that we are not to come before the LORD knowing that we’ve sinned against our neighbor and not yet made the attempt to gain his forgiveness. Not only must we forgive others in the way that God forgives us (Matt 6:14-15) but Jesus adds a gotcha! Before coming into the presence of God, one must first seek forgiveness from those people whom we have offended. Thus, if I know I’ve sinned against my neighbor but have not attempted to reconcile with him, God may well withhold His forgiveness of me. Reflect on this!
This was just as difficult to fulfill back then as it is today. You may be interested to learn that later Jewish tradition incorporated a similar teaching into its Yom Kippur festival. Today, faithful Jews use the week of Yom Kippur to seek out individuals they may have offended in order to repent for their offense. 
Now go and study!
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