You think Cliff is the biggest Winter signing in the last twenty years? Obviously then you forgot about Walter Backman. Big Wally was signed to a two year deal with the Phillies on January 8th of 1991.
Former first round pick Backman had some good years in New York, especially the championship year of 1986 when he hit .320 in a platoon with Tim Teufel. Unfortunately for the Phillies, when he signed a two year $1.3 million contract in 1991, his best years were behind him. He hit .292 with the Pirates (Phucco!) the year before he signed, but after hitting .249 in only 136 games over two seasons in Philadelphia, Backman lasted only 10 games and 31 at-bats with Seattle before retiring.
Backman started coaching after his playing days and won Sporting News' "Minor League Manager of the Year" in 2004. Because of his success, he was hired as manager of the Arizona Diamondbacks. However, the Diamonds (apparently) were unaware of certain things in Backmans past, like multiple arrests and owing the IRS a bunch of money. Saying that Backman lied about his past, he was fired before ever coaching a game.
Backman got back into coaching through the independent leagues and last check was skipper of the Brooklyn Cyclones.
The following video is from the documentary "Playing for Peanuts" which was done while Backman was coaching the South Georgia Peanuts of the now defunct South Coast League. It's funny but it is completely NSFW due to Backmans love of the "F word." If you are at work, plug in some headphones. If you are at home, earmuff your children. Then enjoy.