Top five winners by prize money over multiple days

Brad Rutter at $4,938,436

Ken Jennings at $4,370,700

James Holzhauer at $2,962,216

Matt Amodio at $1,518,601

Amy Schneider at $1,382,800

Top five winners over consecutive winning days

Ken Jennings 74 episodes in 2004

Amy Schneider 40 in 2022

Matt Amodio 38 in 2021

James Holzhauer 32 in 2019

Julia Collins 20 in 2014

Top five winners by prize money in a single day

James Holzhauer at 86,905 to 131,127 in 2019 (1 to 12)

Matt Amodio at 83,000 in 2021

James Hozhauer from 79,633 to 80,615 in 2019 (14 to 17)

Roger Craig at 77,000 in 2010

Ken Jennings at 75,000 in 2004

After you factor in James Holzhauer winnings ranging from 86,905 to 131,127 for the top 12 highest scores in a single day, then you get the above. I could've listed him as the top five, but I wanted some variety in there. Now it's up to the next challenger to see if s/he can beat any of these winning streaks or money won.