The Gemara tells of three people in history who offered an improper/arrogant prayer, yet due to their sincerity and desperation, were granted their request.
The first was Kayin, who after murdering his brother Hevel and realizing the enormity and consequences of his actions said to Hashem, גדול עוני מנשוא - Is my sin too great to bear; meaning, is my sin beyond the endless power of Hashem to forgive.
The second was Eisav, who after being "tricked" by his brother Yaakov and seemingly losing out on getting the blessings from Yitzchak Avinu, cried bitterly, "הברכה אחת יש לך אבי" -Do you have only one bracha, father; meaning certainly you are great enough to have more blessings to dispense.
The third was King Menashe, the idol-worshiping and idol-spreading son of King Chezkiyahu, who after being captured by barbaric pagans and facing certain death at their hands (and mouths) first turned to all his idols for help and when none was forthcoming, he cried to Hashem, "If you also turn a deaf ear to my pleas, I and everyone will know that you are as powerless as every other idol" (chas v'shalom).
The common denominator in all these cases is that though these individuals had committed the foulest of crimes and only turned to heaven when painted into a corner with no other way out, and even then offered a seemingly disrespectful prayer, still just because the did turn to Hashem, their offering was regarded by Hashem purely on it's standalone merit and all were answered in the affirmative.
Can you get a group lower then these 3? Even the roshei taivos of their 3 names E -isav, M- enashe, K -ayin make up the word Emek= valley/depth.
Certainly none of us can compare to the wickedness of these individuals, to have sunk to their depths, yet possibly too often we also only turn to heaven when our Earthly options run out.
As we approach Elul and will be saying the Shir Hama'alos Mima'akim (from the depths), may the Hashem who elevated even the most hardened criminals in his infinite mercy, have pity on us and raise each one of us from our personal abyss to our rightful lofty place next to His Holy Shechinah
