CHICAGO (CBS) — The windows at the Syd Jerome menswear had to be boarded up yet again after the rash of looting early Monday morning – and for employees, boarded-up windows have almost become routine now.

Syd Jerome, 20 N. Clark St., has been an icon in Chicago’s Loop for many years. It has also been hit four times by theft or looting since December of last year.

On Thursday, Scott Shapiro watched video of his store getting looted this week.

“If you notice, they take their time,” he said.

Shapiro told CBS 2’s Marissa Parra it almost felt like déjà vu.

“I’m very discouraged,” Shapiro said. “This has happened four times in the last seven months/.”

And for Shapiro, Syd Jerome is not just a store – it’s personal.

“The doors are covered in blue flannel,” Shapiro said. “My father loved the color blue.”

The iconic menswear shop has been around for more than 60 years. With close to nothing in his pockets, Scott Shapiro’s father, Sid Shapiro, opened the store in 1958.

The store has been paying it forward with the people who came in ever since.

“He allowed them to take merchandise, pay when they could,” Shapiro said.

Sid Shapiro died in 2018. Scott Shapiro follows in his father’s footsteps, keeping the family business going. But he is finding that harder and harder to do every day.

In December, Shapiro was injured and had to go to the hospital after confronting robbers. Just weeks later in January, it happened again, in what Shapiro called a “smash and grab.”

Fast forward four months, well into the COVID-19 pandemic, and Syd Jerome was hit during the civil unrest in the wake of the George Floyd protests in late May.

And looking the photos from this week less than three months after that, Shapiro said he couldn’t even tell the difference anymore.

“It affects families!” he said. “It doesn’t affect just a store or glass or merchandise. It comes out of our pockets.”

To add it all up, lost sales from the pandemic amount to about $1 million and counting. From theft and looting so far, add on another loss of $100,000 or so.

“We’ve got one foot out the door,” Shapiro said. “My employees know it. I know it. My vendors know it. My landlord knows it.”

To Shapiro, it is so much more than the broken glass. All of the broken stuff is a big reason why more jobs – and a piece of history – may not come back.

“I frankly don’t know how we’re going to continue to survive if we keep having incidents that have transpired in the past,” he said. “We’ll be out of business and the city will lose part of its legacy.”

As for how sure he was that Syd Jerome would stay around, Shapiro said, “It’s up to our leaders,” and, “If it doesn’t get any better, we’ll have to go.”