This paper examines the period between 2000 and 2011 in the Jamaican telecommunications industry as it evolved from being a monopoly to vibrant competition to an emerging monopoly in eleven years. The process could be termed the„ boomerang effect‟. In 1999, the government of Jamaica decided to liberalize the telecommunications industry which was completed in 2003. With liberalization the incumbent, Cable and Wireless Jamaica (C&WJ) (renamed LIME), encountered competition from new entrant Digicel in the mobile segment and Flow in the landline and internet segment. Digicel quickly supplanted C&WJ in the lucrative mobile market. In 2008, Digicel entered the El Salvador and Honduras markets which are dominated by American Movil. In apparent retaliation, American Movil entered the Jamaican market and relentlessly targeted Digicel in their biggest market, vowing to supplant them as number one. In March 2011, in a move which surprised analyst, Digicel Jamaica signed an agreement with rival American Movil (trade name, Claro) to acquire Claro Jamaica and in return Digicel would sell its businesses in El Salvador and Honduras to American Movil. The unexpected deal threatens to create a new monopoly in Jamaica. The paper highlights several issues including the powers of the regulatory bodies in dealing mergers and acquisition, network effects, sustaining competitive advantage, international competition and technology standards.