This trade was with the Orioles for Mike Boddicker. The second prosepect that the Sox included in the deal was Brady Anderson. While in hindsight this deal looks like a terrible turn for the Sox, it wasn't that bad at the time. Boddicker came to the Sox and won 7 games playing a key role in leading the Sox to the division title including winning the game that assured the Sox a tie for the title.
Was it worth it? Well, it's easy to look back and say no. But if you were Lou Gorman and looking at a shot to get to the World Series and deliver the first championship since 1918 are you gonna tell the fans to wait to next year?
Most prospects don't pan out and there's hardly ever a sure thing. Look at the other thread with the Gammons article about Toe Nask. Look at all the trades the Yankees have made over the years that have decimated their farm system. How many of those prospects have turned into a Curt Schilling caliber player? Eric Milton, Willie Mo Pena, Drew Henson, Cristian Guzman, etc. And those are only the ones that are remembered.
Point being you have to make trades to improve your team when you're close. That's your job as a GM. Trades don't make a GM great. They're a component, but sometimes you have to make a trade that looks bad five years afterwards, but if you have a solid farm system and are prudent in free agency, you'll have the players in there to replace them and your team will be winning.
This is why Duquette was a bad GM in spite of the Tek/Lowe deal. He decimated this teams farm system and even after three years of heavy spending on development, we still haven't gotten to the point we want to be. It's also why in spite of the Schilling deal (and Bagwell deal), that Gorman wasn't a bad GM. In 1986, he played a key role in developing both World Series teams, building the Sox for two years as their GM and drafting/signing Doc Gooden, Daryl Strawberry, Lenny Dykstra and Kevin Mitchell when he was the Mets. (Of course he also drafted Roger Clemens. No not with the Sox, but with the Mets. Fortunately for us, that Clemens didn't sign.)