Boston workers and residents learned this week that Walsh has signed an agreement with the United States Olympic Committee that bans City of Boston employees from speaking negatively about the Games or the bidding process. The decree says:

The City, including its employees, officers, and representatives, shall not make, publish or communicate to any Person, or communicated in any public forum, any comments or statements (written or oral) that reflect unfavorably upon, denigrate or disparage, or are detrimental to the reputation or statute of, the [International Olympic Committee], the [International Paralympic Committee], the USOC, the IOC Bid, the Bid Committee or the Olympic or Paralympic movement. The City, including its employees, officers and representatives, shall each promote the Bid Committee, the USOC, the IOC Bid, U.S. Olympic and Paralympic athletes and hopefuls and the Olympic and Paralympic movement in a positive manner.

The decree nears iffy legal territory because it’s so broad and seems to apply to all city employees, says Curtis Summers, a labor and employment lawyer from the Husch Blackwell firm. Employees at private companies have few free speech rights except for those related to improving their workplace and guaranteeing their rights as workers. But the Supreme Court in a June 2014 decision clarified the limits public employers can place on their workers’ speech. The court ruled that speech outside the scope of an employee’s duties is protected.

So, Summers says, if a school employee in Boston says that she doesn’t want to deal with tax increases related to the Olympics and the city tries to enforce its decree against her, that could be a violation of her free speech rights. On the other hand, if an employee in the city’s public relations office speaks ill of the Olympics bid, Boston would likely have more enforcement power against those comments since the PR employee’s main responsibility is to speak publicly on behalf of the city.

“The basic principal is that public employees still have the First Amendment right to speak out as citizens on matters of public concern so long as it doesn’t disrupt their ability to do their jobs,” says Sarah Wunsch, deputy legal director of the American Civil Liberties Union of Massachusetts.

Mayor Walsh defended the decree to The Boston Globe, saying that it’s not his intention to cripple open debate about the Olympics and that he has no plans to reprimand or punish city workers for voicing their opposition to the bid for the 2024 Games. When asked why he signed the decree if that was the case, Walsh said that the agreement was “boilerplate.” The USOC has said that the non-disparagement language is typical of contracts between the organization and bidding cities.

“You can call it boilerplate, but boilerplate has meaning,” Wunsch says. The decree will have a chilling effect on free speech, she says, because it frames supporting the Olympics as positive and being critical of the bid as negative. “If you’re a city employee, you know what [the mayor] thinks.”

The mayor’s office did not return Fortune’s request for comment on the decree’s enforcement and its potential infringement on employees’ First Amendment rights. The USOC also did not immediately respond to a request for comment.

While the legality of the decree may be in question, here’s something that’s not: it’s usefulness.

If the goal of Boston’s ban on Olympic smack talk is to breed the cooperation needed to win and put on a successful Olympic Games, encouraging employees to bottle up their grievances could deliver the exact opposite effect.

“Having a way to deal with dissent is a concern for companies more broadly; they want people to disagree so they can come up with better solutions and build consensus,” says Adam Cobb, a professor at The Wharton School. The Boston ban “has the potential to be counterproductive,” he says. “If you don’t let [dissenters] voice their concerns, they’ll just sit there mad or quit.” Those left behind will simply be yes-men and yes-women. Sure, they will all be on the same page. And they’ll come up with nothing but the same solution for the same problem, again and again.