Any tech guys here that can date the newspaper he is holding

[ahnakneemoose]

8. (Also Possibly): Boston Globe 26 October 2004 Red Sox World Series Newspaper

From the Internet:

This image shows a vintage newspaper clipping featuring a baseball player in a batting helmet, likely from a historic sporting event.

The player appears to be wearing a helmet similar to those used by the Boston Red Sox during their 2004 World Series win.

The text alongside the image appears to match a report or historic account of a major baseball game. Newspapers from this era featuring notable sporting moments are often sold as collectibles.