Our product is not Jamaica, but the Reggaeboyz from Jamaica and their football worth...so the company looking to spend on that product must see a vast ROI.
Nike would go with India for 2 reasons, size of market and production opportunities. With the Jamaica reggaeboyz brand what would be their reasons?
Mr.Phoqry, I am not sure I follow you but I do have some questions for you.
NIKE, PUMA, ADIDAS etc are primarily athletic wear correct? No apparel clothing company in the WORLD have or will EVER limit their appeal to any small group.
With that being said, I would just like to inform you that over 50% of the kids you see wearing Jamaica jersey's or PUMA "Jamaica" sneakers in the USA (trying to look cool)........knows NOTHING about soccer or track and field.
Now maybe you can tell me what team or teams the following players play for?
Shawn Carter aka Jiggaman
Curtis Jackson aka 50 cents
Is there a Tuff Gong FC or Tuff Gong track team/club?.......Maybe ADIDAS was endorsing Rohan 
I will leave it at those two for now.....
If you are promoting even plain old water........you want to package your product to reach as many consumers as possible.
Every company in the world has one thing in mind and that is money!!! They will sell their mother to get it.
Trust me boss, Madison Avenue and or share holders on Wall Street don't care how you get the money......
JUST DO IT.HAVE YOU EVER SEEN THE PICTURE OF THAT CHRIST LIKE FIGURE WEARING SOME NIKE SHOES?............
Anyway I was in Canada prior to the 1998 World Cups and they were running some ADIDAS commercials with BOB MARLEY playing football.......... Based on your statements,I am still trying to figure out who they were appealing to IN CANADA with a commercial like that since BOB was not a CANADIAN or a world re-known FOOTBALLER........and the Reggae music in the back ground.....REGGAE?...FOOTBALL....CANADA?...what was that all about?? 
We should not cloud our thoughts with the fact that our music is loved and Jamaica is well known...No, we should consider that football fans buy football jerseys and the size of the market for our jerseys has diminished, hence the difficulty in landing kit deals for the past 2 years....
For the record I own 4
HOCKEY jerseys.......

Maybe it's just an anomaly... or maybe pop culture is a hell of a thing.