Yes, thanks.

If it's "winningest" in $s it might go to whatever gun John W. "Bet A Million" Gates was using
https://books.google.com/books?id=taMfAAAAMAAJ&dq

Nov. 10, 1900 Sporting Life



$150,000 = about $3,750,000 today

Gates really was a Live Bird competitor; I've found reports of his participation at Carteret, and Palm Beach, FL
http://library.la84.org/SportsLibrary/SportingLife/1904/VOL_42_NO_25/SL4225019.pdf