He's sailing close to the wind with his comments about the boss.
Он рискует своими комментариями о начальнике.
Definitions
To sail close to the wind (in a boat) means to steer a sailing vessel as near as possible to the direction from which the wind is blowing, without losing forward motion or causing the sails to luff. This is a technique used to maximize progress toward a destination that is upwind.
