1915 Cracker Jack Ty Cobb
The molasses-flavored, caramel-coated snack has been around for as long as baseball has, more or less. In fact, Cracker Jack had been immortalized in baseball lore by the 1902 song “Take Me Out to the Ballgame”. To this day, fans are still singing the line “Buy me some peanuts and Cracker Jack!” at baseball games. Well, Ty Cobb drove pitchers crazy for more than 3 decades. Ninety years after his retirement, his career .366 batting average is still the top for all Major League Baseball players, both past and present. A PSA 9 1915 Cracker Jack Cobb card sold for $432,000 in 2016.

1915 Cracker Jack Ty Cobb
1948 Leaf Satchel Paige
It’s rather uncommon for a rookie card of a 42-year-old pitcher to be so rare and in demand. However, Leroy “Satchel” Paige was not another common pitcher. He just might have been the most dominant hurler in history. He didn’t get the chance to show off his charisma in the majors until 1948. The legend stepped into the game with no problem, going 6-1 for the world champion Cleveland Indians. In 2018, a PSA 8 copy of this card sold for $432,000.

1948 Leaf Satchel Paige