I took away a much simpler and more boring reason for them showing us the Red Sox label on the tape.
I thought the writers were trying to give us a time frame for the video. As in, one of Ben's men filmed the video and sent it via satellite feed to the island, at which time been recorded it over the Red Sox game. Meaning that the footage of Widmore could be only a few weeks old.
I think Ben could have learned about Widmore's attempts to get to the island through the real Henry Gale. Henry Gale's hot air balloon had a Widmore Industries logo on it. I'm betting the real Henry Gale had information on him relating to his mission. I could see this as the point he realized Widmore was attempting to find the island and therefore he has been sending people to spy on Widmore ever since.
We can see by the video that one of Ben's men got caught, but we know that there's at least another, the person whoi filmed the video. Maybe the filmer is Ben's man on the boat. Maybe if there's some kind of wierd time thing going on, Michael is the filmer and man on the boat. It would at least make Michael as the man on the boat more interesting.
The Red Sox Tape
The prime cast.
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