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It's fine to wax nostalgic for the good old days when the Yankees ruled the universe. I know I certainly do. But let's try to keep our history in clear enough view that we can be grateful for the things we have.
Imagine if George was still around. The payroll would be $350M, and the farm system would be empty. But we'd have MOAR STARZ!!!
Larry Gura for Fran Healy
Fran Healy was a backup catcher. But someone had to work on the days that Thurman Munson needed off, so the Yankees got Healy. What they gave up for Healy was a 27-year-old starter who'd just pitched 150 innings for the first time in his career, to a league-average ERA.
Modern equivalent: probably trading a David Phelps for the Orioles' Caleb Joseph.
Steve Trout
Trout was a solid pitcher before his trade to the Yankees. A case of the yips (nine wild pitches and 37 walks in 46 innings), and that's what they call a career. As far as I know, Trout was one of the original "can't hack it in NY" players. Unfortunately, one of the guys that the Yankees gave up, Bob Tewksbury, went on to have a thirteen-year career highlighted by three 200-inning seasons and a third place finish in the 1992 Cy Young voting.
Modern equivalent: I most think of Trout as the precursor to Javier Vazquez. It's not the trade that was bad; Trout was a perfectly average pitcher for the first eight years of his career. The disaster was that he was such a headcase.
Jay Buhner for Ken Phelps
The immortal Seinfeld trade.
Modern equivalent: Buhner hit .279/.351/.514 in Triple-A at 22 years old. No. 2 prospect Gary Sanchez just hit .270/.338/.406 in Double-A. So imagine if the Yankees traded Sanchez this offseason for Adam LaRoche. Now imagine that they completed that trade in a season where their All-Star first baseman and his iconic mustache hit .311/.353/.462 and played 144 games. 1988 was a weird year.
Willie McGee for Bob Sykes
Willie McGee had an 18-year career, three gold gloves, a silver slugger and was the 1985 MVP. What he did not have was a single game in Yankee pinstripes. The guy the Yankees got for McGee, the immortal Bob Sykes, also never pitched well enough to get into a game for the big league club.
Modern equivalent: McGee was hitting .289/.357/.375 as a 20-year-old splitting the season between Single-A and Double-A with the Yankees. We can all agree those are not amazing numbers. But to trade a guy that young and to get absolutely nothing in return, it would be a bit like trading Ramon Flores to re-acquire Vidal Nuno.
Hideki Irabu
My issue here has less to do with the acquisition of Irabu (heck, I'm still ok with the signing of Igawa; it's not my money). But let's not forget what George called Irabu when the gentleman from Japan failed to cover first base during spring training.
Modern equivalent: Thank goodness George didn't live to see Carlos Beltran's regrettable moment in right field.
Mike Lowell for Ed Yarnell and others
Modern equivalent: You know the season that Aaron Judge just had in A-ball? Mike Lowell had a similar season in Triple-A and he played Gold Glove defense. Those 90s Yankees rolled on anyway, but I wonder what the team would have looked like with Lowell at third. Could he have turned the double play in Game 7 2001? 2003 would certainly have played out very differently, with him in pinstripes instead of in the opposite dugout.
Fred McGriff for Dale Murray
McGriff hit a ton of home runs, and made a not-quite-strong-enough case for the Hall of Fame. He was an 18-year-old in the Gulf Coast League when he was traded for a 33-year-old Dale Murray. Murray managed to post ERA+ of 87, 78, 34 over the final 100 innings of his career, to bring his career ERA+ down to exactly 100.
Modern equivalent: Who's your favorite Baby Bomber? Luis Torrens or Jorge Mateo? Well, the Yankees just traded him for Joba Chamberlain.