Ed Wineapple
I) Ed Wineapple --> '29 Washington Senators --> Joe Cronin, Nick Altrock
II) Cronin --> '45 Red Sox
II) Altrock --> '33 Washington Senators
Cronin's my only choice here, but I added Nick Altrock here for a reason. As I was looking through the '29 Senators team, a number next to Altrock stuck out for me - 52. It was under the age column! Altrock's career spanned 35 years until his last season in 1933 at the age of 56. Remarkable! This guy was Minnie Minoso before there was a Minnie Minoso! I may have to look into this player further, but I may have an outside chance to connect someone who played in the 1800's.
Back to Cronin...
II) Cronin --> '45 Red Sox --> Jim Wilson
III) Wilson --> '58 White Sox --> Norm Cash, Johnny Callison, Luis Aparicio
IV) Aparicio --> '73 Red Sox
IV) Callison --> '73 Yankees
IV) Cash --> '74 Tigers
The Yankees and Tigers teams are connected, not that I wouldn't have picked a Hall of Famer on a Red Sox team above them anyway.
IV) Aparicio --> '73 Red Sox --> http://www.blogger.com/img/blank.gifCarlton Fisk
V) Fisk --> '93 White Sox --> Jason Bere, Frank Thomas, Tim Raines
VI) Bere --> 2001 Cubs
VI) Raines --> '99 Athletics
VI) Thomas --> 2007 Blue Jays
Done, although this makes the Altrock rambling a moot point. If I could have completed this in 5 or less, it would have been worth exploring.
1. Ed Wineapple played for the 1929 Washington Senators with Joe Cronin.
2. Joe Cronin played for the 1945 Boston Red Sox with Jim Wilson.
3. Jim Wilson played for the 1958 Chicago White Sox with Luis Aparicio.
4. Luis Aparicio played for the 1973 Boston Red Sox with Carlton Fisk.
5. Carlton Fisk played for the 1993 Chicago White Sox with Frank Thomas.
6. Frank Thomas played for the 2007 Toronto Blue Jays with Matt Stairs!
Degrees of Matt Stairs: 6
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