Armed agents in tactical gear threw flash-bang grenades to disperse a crowd in Los Angeles’s Fashion District. Later, agents fired less-than-lethal ammunition at protesters outside a detention center.

Federal agents in tactical gear armed with military-style rifles threw flash-bang grenades to disperse an angry crowd near downtown Los Angeles on Friday as they conducted an immigration raid on a clothing wholesaler, the latest sign of tensions between protesters and law enforcement over raids carried out at stores, restaurants and court buildings.

The operation was one of at least three immigration sweeps conducted in Los Angeles on Friday. In another one, federal agents converged at a Home Depot where day laborers regularly gather in search of work.

The raid at the clothing wholesaler began about 9:15 a.m. in the Fashion District, less than two miles from Los Angeles City Hall.

It was an extraordinary show of force. Dozens of federal agents wearing helmets and green camouflage arrived in two hulking armored trucks and other unmarked vehicles, and were soon approached by a crowd of immigrant activists and supporters. Some agents carried riot shields and others held rifles, as well as shotguns that appeared to be loaded with less-than-lethal ammunition.

Agents cleared a path for two white passenger vans that exited the area. A short time later, as officers boarded their vehicles to leave, a few agents lobbed flash-bang grenades at groups of people who chased alongside the slow-moving convoy. Some protesters had thrown eggs and other objects at the vehicles. At one point, the vehicles snagged and crushed at least two electric scooters that protesters had used.

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