After the 1988 season, the Yankees decided that they were done with second baseman Willie Randolph. He had been with the team for 13 seasons, playing an exemplary second base and doing a fairly consistent job offensively with a skill set that was broadly similar to Luis Castillo’s, except that Randolph had fewer steals, more walks and better defense. Yet, there were a few knocks on him. He had always been prone to injuries, missing 20 to 40 games a year. With just a little more durability, he might have had at least a small-c case for the Hall of Fame; primarily a leadoff or number-two hitter, Randolph never scored 100 runs in a season. Part of that was due to the 1970s being a low-offense era, part to the missed time. Randolph could have had a half-dozen 100-run seasons if he had only hung in the lineup a little more often. Instead, he was famous for fragility, not for being a catalyst. The other concern was that, going into his age-34 season, his range was shrinking.
That November, the Yankees signed 29-year-old Steve Sax away from the world-champion Dodgers. About six weeks later, Randolph signed with the Dodgers. It was as if the two players had been traded for each other. The Yankees lost the trade; they got three years of .294/.342/.376 hitting from Sax, which broke down to two good years and one you’d rather forget about. During those same three years, Willie hit .290/.377/.341 and played much better defense (the Yankees were trying to push Sax to third for the immortal Pat Kelly by the end of his tenure), so in terms of wins above replacement, it was Sax 9.7, Randolph 11.8. On the other hand, Yankees GM Gene Michael did a lot to redeem the situation by trading Sax to the White Sox for three pitchers: Melido Perez, Bob Wickman, and Domingo Jean, easily one of the top 20 trades in team history.
No great point here. That was just the first thing I thought of when Jon Heyman wrote that the Johnny Damon would end his offseason odyssey with either the Tigers or White Sox. If the former, then you could almost look at the deal for Curtis Granderson as having been a trade that included Damon.
Parenthetically, I don’ t have a list of the 20-greatest trades in team history ready to back up the claim above, but I know it doesn’t begin with Babe Ruth for $100,000 and the mortgage on Fenway Park. Many of the great trades in Yankees history, from Ruth to Chuck Knoblauch, were one-sided because the Yankees were taking on someone else’s financial problems. There are far fewer trades, like the Sax deal or Sparky Lyle for Danny Cater, that are straight-up good baseball deals. Finding 20 of those is a lot harder than just listing the times that they took advantage of Harry Frazee.