Chaos unfolds in Boston as protests turn violent

By Jerry McConway
updated on October 14, 2025

The city of Boston had a very rough night recently, yet, for the most part, the mainstream media seems to be ignoring what occurred.

According to news reports, the city fell into utter chaos, with police officers subjected to attacks amid a street-racing event. 

Despite all of that, the city’s mayor continues to insist that everything is fine, and Donald Trump is the bad guy here.

The ultimatum

Earlier this year, Trump’s administration gave sanctuary cities in this country an ultimatum, something to which Boston Mayor Michelle Wu took great exception.

Wu held a press conference to respond to a letter sent out by Attorney General Pam Bondi about the directive, stating, "Unlike the Trump administration, Boston follows the law. We keep each other safe in Boston. We don't need an authoritarian administration to come in and try to instill fear and intimidate us like they're doing with cities around the country."

The question, however, is just how legal sanctuary cities actually are.

The U.S. Supreme Court has repeatedly ruled that immigration is a federal issue, yet somehow, cities and states have been able to circumvent federal law by declaring themselves sanctuary cities. It makes no sense, which is why the high court needs to take up this issue ASAP.

Boston prosecutors start dropping the hammer

While Wu and company have stated that all is okay in Boston, it was interesting to see prosecutors in the city announce that more serious charges would soon be filed against rioters there.

Kevin Hayden, the district attorney for Suffolk County, which includes Boston, stated, “If you assault police and commit other offenses, you’re going to be arrested and prosecuted, period.”

Massachusetts Gov. Maura Healey added, “There is no tolerance for blocking roadways or assaulting police. Anyone who does should be held fully accountable.”

This is a big change from what we have seen in the past, when rioters have been given nothing more than a slap on the wrist, and it signals a major shift in how the city and state are going to start dealing with these groups.

Blue city takeover

Then comes the aforementioned incident in Boston, in which an early morning street racing event turned ugly on Oct. 5, and officers were attacked by more than 100 people with fireworks, cones, poles, and just about anything people could get their hands on at the time.

Boston Police Patrolmen's Association President Larry Calderone stated, "What happened last weekend got out of control, it went through four different communities, ended up here at a couple of locations in Boston. And each location that they went to in this past incident, it appears as though they got more aggressive.”

He continued, "And when they ended up in the downtown South End section of Boston, that pretty much in our opinion looked premeditated."

This is what happens when you extend that leash on violent conduct: people become more emboldened and start to test just how much rope you are going to give them. We see this more and more in Democrat-run cities, as liberal leaders continue to spew anti-police rhetoric and anti-immigration enforcement rhetoric. Yet, while people complain about the violence, they continue to elect those same Democrats to office.

About Jerry McConway

Jerry McConway is the Senior Editorial Director at American Digest Media, as well as the featured columnist on Real Talk Digest. He has been covering politics for more than a decade. His no-nonsense writing style makes him enemy number one in DC. His mission is to tell the truth to readers, good or bad, something the mainstream media has failed to do for decades. What sets Jerry apart from his competition is reader loyalty. They don't always agree with him, but they know he tells them the truth. Love him or hate him, you can't ignore him.

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