Sailors have a tendency to apply terminology related to ships to other aspects of life. A jib is a small triangular sail before the main sail on large ships and cutters. Many countries used different cuts and displayed their colors on the jib. When "cut of the jib" is applied to men, it means "your stylistic choices" . Treebeard/Tree/Treeman/Treymon has a way of making a point with whit, that cuts right to the heart of the matter. Many people here are crazy excited about "financial flexibility" and high draft picks when neither of those things mean anything if the Cubs are not trying to win at the major league level. I hope that helps. Well you sure took the wind of out his sails. Oh buoy, here come the puns