Conventional wisdom says the best trades are even for both teams. Personally, I’ve always preferred deals that are lopsided in the Cubs favor. On December 8, 1988, the Northsiders fleeced the Cincinnati Reds. We just didn’t know it at the time.

During that offseason, GM Jim Frey sent outfielder Rolando Roomes to Cincy for 29-year-old utility player Lloyd McClendon. At first it seemed like a meaningless transaction. McClendon was too old to be a prospect, and he had shown little prowess at the plate in two Major League seasons. His potential value for the upcoming 1989 campaign appeared to be his versatility. McClendon had experience at multiple positions.

It didn’t take long for his right-handed bat to come around. As a platoon player vs. LHP, McClendon was hugely valuable to a team that would end up in the postseason:

.339/.432/.554, 6 homers in 121 at bats

Paired with rookie Dwight Smith, McClendon helped turn LF into a productive offensive position for the 1989 Cubs. In addition, he filled in all over the diamond, playing 28 games at 1B, six games at 3B, and five games at catcher.

Unfortunately, McClendon was only a one-year solution, as he moved on to Pittsburgh the following year. And what about our friend Rolando Roomes? Well, Mr. Roomes enjoyed an uneventful career, hitting .254 with no power or plate discipline in his three seasons. He was out of baseball by the age of 28.

OK, so the Cubs didn’t pull a “Jeff Bagwell for Larry Andersen” deal, but it certainly was a swindle. Nice work by the late 1980s front office. If only the current bunch could pull off a similar fleecing or two.

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