Hello there! I come to you to share the story I will soon present to my players: How Ismark got his nickname and why some Barovian citizens dislike him:

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If they learn the nickname and ask Ireena she will tell them this: About four years before the start of the campaign at a time of night before or after the march of the dead Ismark was drinking at the Blood on the vine and apparently a group of adventurers came into the tavern celebrating a recent victory, seeing their happiness Ismark offered some drinks, but another stranger seemed to take offense to this began to berate the party. Ismark did not like this and as a gentleman he dared the man to a duel, if he (Ismark) won the man would have to apologize and pay for the drinks if he (the stranger) won Ismark would have to pay for his drinks for the next week.

The duel took place outside with the sisters that own the tavern and about 20 Barovians standing under moonlight and firelight to observe this event, as Ireena recalls the confrontation was very close with sparks, parries, and maneuvers from both sides; Ultimately something happened that made Ismarks pants loosen and fall around his ankles forcing him to the ground where the man proceeded to kick dirt into his face and stomp him down. It was declared that the stranger won and he took Ismarks coin purse and threw at the feet of the owners, the man was never seen again and word spread of Ismarks humiliation eventually reaching his family. Being a man of pride Ismark does not share this story and works every day to better himself and regain the respect of his people.

NOW. If the party inquires about this to either of the three sisters or finds one of the witnesses that night they will get this story:

The night is the same, but the sisters had a special visitor and a celebration: One of their cousins in the land had a big birthday (Coming of age, celebration, awakening to the innate power, whatever you feel like) And they were hosting her, some other family members and friends; They actually invited Ismark because even at that time he was a charismatic man and a bit of eye candy amongst Barovians. The tavern was not "Closed" for the night as any other attendee would inconsequential... That is until a tall, pale, blonde man entered the tavern, he was rather handsome and attracted the attention of the young women in attendance. The man partook in drinks but only seemed to be interested in the men of the party being rather flirtatious, later in the evening as alcohol was running smoothly one of the women approached the man and put the moves on him which seemed to greatly offend him, this stranger began to disparage the women in attendance going after their looks and attitude with sharp remarks and acrid insults giving off this dangerous aura. Ismark could not stand for this and so the duel was proposed, same stakes as before.

The Vistana family and few Barovians that heard the commotion gathered outside again to witness what would probably be the most entertaining thing to happen for the next six months; The duel began and whoever is telling the story will remark how handily Ismark was dealing with the stranger, it was obvious that while the stranger exuded dangerous energy the young noble had dedicated his life to the sword, practicing with his father from a young age. When the result of the bout was almost decided Ismark suddenly backed away swinging his blade to the air while calling out something along the lines of "Back away! Take cover, I will deal with these foul Vermin! Do not fear!" his swings were still stylish which made the onlookers think the man was only showing off but in his distraction, the man got back on his feet and cut through Ismark belt causing him to trip over as he backed away.
The stranger proceeded to kick, cut, stomp, and smear Ismark for a prolonged time, the onlookers enthralled in a mix of disgust and fascination. Eventually, the man backed away, spit on Ismark and walked away and out of town, the young noble was left on the ground until morning came where he walked shamefully towards his home covered in blood and mud.

Ismark still remembers that strangers face and has sworn to regain his pride.

That man as the title implies was Escher, bored out of his mind as Strahd hibernated followed the large Vistana caravan to Barovia looking to feed one townsman but gained a valuable lesson. He wasn't actually hurt during the duel but Ismarks skills kept him from retaliating, he ultimately used an illusion/charm effect available to him as a bard to distract Ismark and kick him down.