Well, with the news out of England concerning which clubs are going up, and which are going down, along with the finalization of the lower leagues player movement starts. This is a time when clubs announce who will be cut loose, who will be resigned, and who will go on the transfer list.
In MLS while names like Henry and Owen tend to attract attention, it is much more likely that MLS finds guys that are Free Agents and tries to bring them over the Atlantic. While the MLS transfer window doesn't open again until July 15th it is in the next nine weeks when an enterprising GM must start to find that talent.
So start searching for those Frees again. I'm going to try and focus on Americans/Canadians (because having an open international slot in midseason is tough), but CONCACAF players will likely get some attention as well.
In fact my first two are both from T&T.
Stern John and Dennis Lawerence are now both Free
Lawrence is an older defensive giant (6'6) who has played for Crewe, Swansea, Wrexham and Defence Force. With the dearth of centerbacks in MLS he's one who deserves a look, or two.
Stern John has played a ton of American soccer, and made MLS good money on a transfer in the late 90s. From the previous linked piece he will likely stay in England, but he would be a solid addition for a club with offensive troubles.
When I say that clubs are cutting guys, I mean a TON of guys.
Championship, League One, League Two, Scotland, Ireland, Wales should all have guys in MLS pricing range, generally speak the dominant language of MLS, and would have the easiest time culturally.
Any Frees that intrigue you at this time?
Version One was in the 08/09 Transfer Window