“I’m dreaming of a white Christmas” is a famous line in Irving Berlin’s classic Christmas song, “White Christmas” (1942). A “white Christmas” joke was cited in print in a 1932 newspaper column by Ted Cook—ten years before the song:
 
“And it may or may not be a white Christmas, but it’ll put most of us in the red.”
 
“In the red” means financial losses. “We are not sure whether we’ll have a white Christmas or a green Christmas, but one thing’s sure; the aftermath of Christmas is going to see most of us in the red” was cited in a 1935 newspaper.
 
A popular newspaper chuckle was printed in December 1972:
 
“About all you can do is dream of a white Christmas—seems like it always leaves most of us in the red.”
 
“I’m dreaming of a white Christmas, but if the white runs out, I’ll drink the red” is another “white Christmas” joke.
 
   
Wikipedia: White Christmas (song)
“White Christmas” is a 1942 Irving Berlin song reminiscing about an old-fashioned Christmas setting. According to the Guinness World Records, the version sung by Bing Crosby is the best-selling single of all time, with estimated sales in excess of 100 million copies worldwide. Other versions of the song, along with Crosby’s, have sold over 150 million copies.
 
13 December 1932, The Salt Lake Tribune (Salt Lake City, UT), “Cook-Coos” by Ted Cook, pg. 7, col. 6:
And it may or may not be a white Christmas, but it’ll put most of us in the red.
 
21 December 1935, Lock Haven (PA) Express, pg. 8, col. 1:
We are not sure whether we’ll have a white Christmas or a green Christmas, but one thing’s sure; the aftermath of Christmas is going to see most of us in the red.
 
1 December 1972, Springfield (MA) Union, “Today’s Chuckle,” pg. 1, col. 7:
About all you can do is dream of a white Christmas—seems like it always leaves most of us in the red.
 
7 December 1972, The Daily Courier (Connellsville, PA), pg. 1, col. 1:
About all you can do is dream of a white Christmas—seems like it always leaves most of us in the red.
 
9 December 1972, Express and News (San Antonio, TX), “Today’s Chuckle,” pg. 1, col. 1:
About all you can do is dream of a white Christmas—seems like it always leaves most of us in the red.
 
Google Books
14,000 Quips & Quotes:
For Speakers, Writers, Editors, Preachers, and Teachers
By E. C. McKenzie
Grand Rapids, MI: Baker Book House
1990, ©1980
Pg. 55:
About all you can do is dream of a white Christmas, for it seems like it always leaves most of us in the red.
 
Google Books
Keep Calm at Christmas
By Ebury Publishing
New York, NY: Ebury Publishing (Random House)
2011
Pg. ?:
ABOUT ALL YOU CAN DO IS DREAM OF A WHITE CHRISTMAS, FOR IT SEEMS LIKE IT ALWAYS LEAVES MOST OF US IN THE RED.
Anon