Yup. One of the most interesting things Vintage does for me is seeing cards that were originally rarely played when released becoming bombs now that they interact with a card considered unplayable in a new set. A perfect example for me was what happened to flash when newer creatures came out. I've had a playset of them since Mirage as I bought a bunch of it when it came out. They just sat in my binder.
Good sentiment, bad example. Flash was reworded in May 2007 to break it just in time for a Legacy Grand Prix in Columbus. The two main creatures that helped to break it, Academy Rector and Protean Hulk, were printed in February 1999 and May 2006 respectively.