It made sense at the time! Defending MLB's worst-ever trades

Evaluating a baseball trade -- particularly identifying winners and losers -- is never a straightforward process.

First, most trades are made by teams in different situations. One might be aimed more at the future, while the other is trying to get over the hump right now. Or one team might be trying to navigate a cluttered payroll, while the other has cleared its books and is ready and willing to take on money. Judging trades is tough when they happen, and even with the benefit of hindsight, it's often not merely a matter of saying, These players produced more WAR than these other players.

That said, trades that turn out to be objectively one-sided have provided some of the more colorful liner notes in baseball history. Once upon a time, a bad deal might have been struck in some hotel lobby, where one back-slapping owner might have shaken hands with a compatriot during the wee hours of the morning.

That kind of swapping is now more myth than reality. Modern teams have numbers-crunchers and grizzled scouts behind every deal they strike and sophisticated models for assigning valuations. Still, bad trades happen. Dealmaking remains an inexact science, often driven by intangible forces for which no trade valuation model can account.

The irony is that every bad baseball deal ever struck made sense to the team drawing the short end of the stick at the time the trade was made. What's more: In most cases, you can argue that the reasoning for that bad trade was sound, when considered in context.

And so we reach our theme for today: What was the reasoning behind some of baseball's most infamous trades?

Perhaps more importantly: Are there lessons from these deals that teams need to take to heart with the 2021 trade deadline approaching?