A foreman in charge of a cattle drive.
- ‘Jack's portly wife, Bertha, invited Laurie to supper, and Laurie was delighted to hear stories that Jack told of being trail boss on his own cattle drives.’
- ‘He creates in his performance of the trail boss a bear-like, almost incoherent characterization that has to be seen to be believed.’
- ‘Forgive me if I think our problem lies less with our cattle wanting to be the main course for the carnivorous Kiwis, than the trail boss who's lost the branding iron.’
- ‘He's been around, a veteran trail boss who knows what he likes (whiskey and hot baths) and knows what he doesn't like (lost cattle, incompetent cowhands).’
- ‘According to the authors, ‘an average crew contained about eleven men: the trail boss, eight cowboys, a wrangler, and a cook.’’