A drilling insert has a central portion with a central axis, and three circumferentially spaced tip portions. Each tip portion has a first axis and two diverging first cutting edges with radially outermost cutting points defining a first circle lying on a tip plane perpendicular to the first axis and having a first cutting diameter. In a view along one of the first axes, a second circle having a second diameter circumscribes the drilling insert, and the first cutting diameter is at least sixty percent of the second diameter. A cutting tool rotatable about a tool axis with a tool cutting diameter includes the drilling insert, and a second cutting insert having a second cutting edge. One of the tip portions is operative having its first axis coaxial to the tool axis, and the second cutting edge extends radially outward of the first cutting diameter.