Once you've mastered the basic boxing punches, you may want to consider adding some other more advanced boxing techniques and punches into your repertoire. The bolo punch is just such a technique. It is not used very often and for reasons you'll soon learn, but if mastered can give you options in the ring. You'll be pretty hard pressed to find a lot of professional boxers who use it and probably even fewer amateur boxers. But, if you look hard enough...
A Famous Bolo Puncher
Kid Gavilan is one of those professional bolo punchers. One of three famous bolo punchers (the other two being Ceferino Garcia and Sugar Ray Leonard), Gavilan said he developed the wide sweeping uppercut motion working in the sugar cane fields as a youth. The machete he would carry was swung in an underarm fashion which he developed into a boxing punch later in life.
While the bolo punch can be an effective punch, it is more commonly used as a distraction. By dropping the back hand and pretending to make an obvious wide sweeping throw, your opponent's eyes gravitate to the dropped hand, leaving you free to throw your front arm. Often you'll see variations of the bolo punch where the boxer will drop the right hand and make circular motions - basically showboating, before throwing a stiff jab or hook with the lead hand.
Over time, your opponent will obviously figure out what you are doing and may then focus on the lead hand. That's when life gets really good for you as you are free to follow through with the bolo punch. Because of the distance and torque you can put into it, it can be a devastating blow when it lands.
The bolo punch is an advanced technique and leaves you wide open, so be aware of that if you plan on using it.
The Left Bolo Punch
Most boxing fans will agree that the monster left handed bolo punch that Ike Ibeabuchi gave to Chris Byrd is one of the most famous bolo punches. See the video above. It resembles a very obvious uppercut. Notice how Ike kind of faked a right - threw it but with very little on it. That transferred his weight to the left which he put every ounce of into that knockout punch.
For more examples of the bolo punch, watch any of Sugar Ray Leonard's fights, in particular his second fight against Roberto Duran and the rematch against Thomas Hearns.