worldseries

"Edith White Bolling Galt Wilson (October 15, 1872 — December 28, 1961), second wife of U.S. President Woodrow Wilson, was First Lady of the United States from 1915 to 1921. She has been labeled "the Secret President" and "the first woman to run the government" for the role she played after her husband suffered a severe stroke in October 1919. She has also been called "the first female president of the United States."
en.wikipedia.org/wiki/Edith_Bolling_Galt_Wilson

A double of her is shown here:

William Joseph "Lefty" Glennon had been appointed Boston mascot in 1915.
rememberjamaicaplain.blogspot.com/2008_01_01_archive.html

A similar picture ran in Baseball Magazine with the caption:
"The rival mascots, Billy Glennon of the Red
Sox and "Red" Monahan of Brooklyn"
library.la84.org/SportsLibrary/BBM/1916/bbm182f.pdf

For Red Monahan, see

Art Siegel: thanks for finding more information on Glennon and Monahan. We will update the record.

John Francis Hylan www.wikidata.org/wiki/Q6233903

The curved detail on the top edge of the wall places Mayor Hylan at the Polo Grounds, as he poses prior to throwing out a ceremonial first pitch. (See comment by Jon (LOC P&P) below). The date inscribed (in reverse) on the bottom of image reads "10/6/24," which would make the occasion Game 3 of the 1924 World Series, between the New York Giants and Washington Senators. The first game of the series to be played at the Polo Grounds. The Giants would defeat the Senators that day, by a score of 6-4, but the Senators would ultimately win the World Series (their first World Series Championship) in seven games. See: en.wikipedia.org/wiki/1924_World_Series

Thanks TVL1970. The New York Times article published on October, 7th, 1924 says Hylan posed for the photographers with a ball, but didn't actually throw it.