On Monday, the police superintendent defended his performance in an open letter published in the Chicago Sun-Times.
Weis says he has received no help from the police union despite repeated requests.
Staffing shortfalls, reassignments to crime hot spots and a lack of communication with the rank and file are all issues Chicago's police union says have led to a protest.
Jody Weis was hired as superintendent following years of police misconduct scandals.
Weis says he has worked hard to repair the trust between the department and the public.
He came in two-and-a-half years ago as the highest-paid superintendent in the history of the Chicago Police Department. From the day Jody Weis took the job, he had one big strike against him: he was an outsider, a career FBI guy.
"I think he is doing the best that he can do, but I think this is a city that you almost need to come up through the ranks to be the boss," said Eric Davis.
Davis recently retired from the department after 26 years on the force. While Davis believes Weis has brought some innovative ideas to the department, he understands the frustration the rank and file feel about Weis' leadership.
"There are many officers that feel they don't have any opportunity to move up or move across laterally; we don't have enough manpower," said Davis.
The fraternal order of police has been highly critical of the superintendent, which prompted Weis to write a letter to the Chicago Sun-Times defending himself.
He wrote in part: "Leadership is not about being popular. It's about making difficult decisions and doing the right thing."
However, the Fraternal Order of Police says an understaffed force combined with leaving the union out of important decisions is not the right thing to do.
"They constantly asked for the input, we give it to them, and it goes nowhere," said FOP
Weis wrote in his letter that the FOP has not offered anything of substance.
Not all are so critical of Weis. Ceasefire Director Tio Hardiman says Weis has grown into the job.
"We are on pace in Chicago to get homicides at the lowest level ever in the last three or four decades, so I think Superintendent Weis is getting a handle on everything now to a degree," said Hardiman.
The homicide rate may be dropping, but several officers say that until more cops are hired, they will continue to feel less safe on the street.
Hundreds of police officers are expected at Wednesday's protest in front of police headquarters at 35th and Michigan.
Davis says he will be at the protest although he also said he thinks Weis should stay on under a new mayor.