A man wearing a blue apron and long rubber boots is dragging a flotation device from a long row of flotation devices.
A worker pulls up his long boots before climbing onto the flotation device.
The man can drag a flotation device without pulling up his long boots or climbing onto one.
Sentence 1 says the man is dragging a flotation device, but makes no mention of him climbing into it. Additionally, Sentence 1 provides no action taken to put on the boots.
Just because a man is getting a flotation device does not mean he will be climbing onto it himself.