Here’s George Woodruff’s portrait of Ted Williams that Fleer used as the photo on the box and wrapper of their 1959 set!
Mastro sold the 8” x 10” portrait in July 1998.
And yes, Topps used the same picture on the Splendid Splinter’s 1954 (#250), 1955, and 1956 Topps cards.
In terms of dating the photo, Memory Lane Inc. sold a Type 1 example for $1,501.20 in October 2017 and estimated the issue date right after Williams’ return from his final 1953 Korean War stint.