For Jamaican clubs, chasing glory in the Concacaf Caribbean Cup is becoming an increasingly expensive gamble, one they can scarcely afford to make, yet cannot afford to walk away from. As the football season gets underway, Jamaica’s top clubs have set their sights not only on domestic glory but also on regional domination. Over the past few years, Jamaica has been at the forefront of the Caribbean Cup, with clubs from the island winning two of the last three titles.