Before I begin this exercise in What If? baseball history, let’s just remember that hindsight is always 20/20. When we look back in time and try to evaluate trades that weren’t made, it’s easy to do it sitting here in 2008. The trick is to put our selves in the shoes of those involved in the decision. In this case, that means hoping in a time machine and journeying to July 31, 1998.
It is July 31, 1998, and the Yankees are on a once-in-a-lifetime roll. The Yankees are 76-27 with a 15-game lead over the Red Sox. Since a 1-3 start, the team was a blistering 75-24. That just doesn’t happen.
But despite being prohibitive World Series favorites, the Yankees were always searching for ways to get better, and leading the charge was a rookie. General Manager Brian Cashman was in his first year as Yankee GM, and a series of moves and non-moves, beginning on that fateful night in July — the trade deadline — would impact the Yankees Dynasty up through the present day.
As site commenter Phil reminded us today, the Yankees were in the hunt for Randy Johnson. I had completely forgotten about these behind-the-scenes moves. But as RAB favorite and one-time Yankee beatwriter Buster Olney relates, the Yankees didn’t pull the trigger: