In 1929, uniform numbers appeared on the back of baseball jerseys for the first time, thanks to the Indians and the Yankees.  By 1937, numbers finally appeared across all uniforms, both home and away, across both major leagues.  Since that time, 81 distinct numbers have been worn by members of the White Sox, while the Cubs boast 76.

Today, we continue our look at those players, picking our favorite, if not the best, player to wear each uniform number for both Chicago teams with #66.  11 players have donned #66 while playing in Chicago, 9 for the White Sox and 2 for the Cubs.

Gerry Staley spent parts of 6 seasons with the White Sox, from 1956 until a June 1961 trade sent him to the A’s.  Over that time, he wore 4 different numbers, one of which was #66. His best season was 1959, as he led the league with 67 appearances and 15 saves, earning a single MVP vote as the White Sox won the pennant and went to the World Series for the first time in 40 years.

Rafael Dolis wore #66 in his one appearance for the 2011 Cubs, throwing 1 1/3 scoreless innings.  He switched to #48 for 2012 and 2013, then disappeared from the major leagues before popping back up in 2020 with the Blue Jays.