The area of concern is on St. Paul Avenue just west of Water Street. One victim said he tried to cross the tracks to get into the left turn lane when his tire got stuck.
"I got severe road rash," said John Rivera, a former Wauwatosa Police Officer who was riding his Harley motorcycle with his wife Monday night when the accident happened.
"That trolley track took a hold of me and we went down," he said.
His wife Taylor took the brunt of the fall, spraining her knee in multiple places and bruising her face so badly, she didn't want to appear on camera.
"I'm just really upset you know," said John. "If there's gonna be accountability for this track and we're going to bring something new to town, make sure no one gets hurt."
The Riveras are represented by the Hupy and Abraham law firm. Jason Abraham says the couple is the third set of riders to crash in the same spot.
"There are some spots that are elevated so you're forced to confront the tracks parallel," said Abraham. "It's very easy to grab a motorcycle or a bike tire."
There is a sign along St. Paul, telling those on two wheels to cross the tracks at a 90-degree angle. A safety video online also demonstrates how bicyclists can get across the tracks.
But Abraham says it's more difficult for those on motorcycles to cross at a 90-degree angle and he's worried about out of town visitors who don't know the tracks are there.
"We wanted the mayor to do something about it, to protect these bikers that are coming to Milwaukee," said Abraham.
His law firm sent a letter to Mayor Barrett on Tuesday, writing in the letter that one responding officer on the accident scene recommended closing the road during Harley activities this weekend, to avoid more accidents.
"I'm sure there's a way to make this safer," said Abraham.
He also explained that these cases are not solely about money, saying the most his clients could get in any kind of lawsuit against the city is $50,000.
"Some of our client's medical bills will exceed $50,000," he said.
We reached out to the mayor's office for comment but were told to contact the Department of Public Works. A spokeswoman there said they are aware of the lawsuits but can not comment on pending litigation.