Your worst trade, ever

[Westheim]

Lopsided trades happen all the time, whether you try to trade fairly () or not, but sometimes it quickly transpires that you just grabbed into a pile of poo. Not talking about the time you traded three guys for the #1 prospect and he only turned out to be an occasional All Star. Here we want to talk about the plutonium (not: platinum) level of horrendous deals that leave long-term fallout and permanent scars, mostly on your soul.

I'll go first!

In 1991, the Raccoons had their division more or less bagged in late July, leading the pack by roughly a dozen games to return to the playoffs for the first time since '89, where their bid for immortality ended with a third extra-inning loss in Game 6 when Glenn Johnston dropped Ed Parrell's soft fly to allow the Wolves to bring the go-ahead and eventually winning run across in the 14th.

1991 appeared to right all that wrong. Johnston was an afterthought at that point, and the Raccoons had a whirring mix of young-and-coming stars like Neil Reece, David Vinson, and Ben O'Morrissey, and established, gritty veterans of the Kisho Saito, Daniel Hall, and Scott Wade caliber. The team was humming, playing well over .600 as the deadline neared, but injuries had taken a tooth or two out of the lineup and I had the urge to improve on things.

Raúl Castillo had missed some time with an injury earlier in the year, but was otherwise cracking it for the Blue Sox, who didn't really have all their heart invested in him, and he routinely came off the bench. Right at that time we had a Daniel Hall-shaped void to fill at corner outfield (due to one of his 6,000 career injuries) and Castillo was a perfect fit. A trade was arranged at the end of July that sent Castillo to the Raccoons, with the Blue Sox receiving surplus outfielder Ennio Sabre (who made no impact for either team) on top of right-hander Dennis Fried.

Fried, 22, had actually made 13 starts for the Raccoons in 1990, and had surrendered 14 bombs and generally mixed results. The reasoning back then was that he had struggled in '90, was struggling in the minors this year, and of his sort we had plenty in the organization and wouldn't notice when one of them was sent away...

How did that go? Dennis Fried got his **** together, spent 17 years with the Blue Sox and led the league in wins twice, in ERA once, and in WHIP five times. He made the Hall of Fame on the second ballot, missing just narrowly on the first.

Raúl Castillo played three games for the Raccoons before running head-first into a wall. A concussion took him out for the season, and the Raccoons let him go afterwards. He hung on for one more terrible outing with the Crusaders the following year, then was washed out of baseball at age 30.

Three games' worth of Raúl Castillo for an entire Hall of Fame career. I will take this one to the grave with me. Try to beat that.

[JasonC23]

I don't think I can top the original post, but I feel like the following story from my long-running White Sox dynasty (started in OOTP15, carried over into every OOTP since) has a similar spirit...

It's the 2030 off-season. Although my White Sox have won the 2029 and 2030 World Series (the first time I'd won back-to-back series since taking over the Sox in 2014), my rotation is getting expensive and old, and I'm paranoid that I don't have enough pitching depth. I mean, I'm always paranoid that I don't have enough pitching depth, but I really, really needed to acquire the next great wave of starters, and fast! I take a quick gander around the league to see if there are any nearly MLB-ready prospects I'd like to try and trade for, and I settle on one: Doug Talley, a promising Arizona Diamondbacks hurler who looks like he could be ready to debut as soon as next season. I ask OOTP to make this trade work, and Arizona wants one of 2 promising young prospects in my minor league system: Pascual Stufi or Ron Wade.

Stufi is a spectacular fielder at all 3 OF positions and has a good-looking batting eye; he should at least develop into a supersub off the bench, and maybe even into a solid starter if he can keep his batting average at not-awful levels. Wade, drafted 553rd overall back in 2027, has developed beyond his humble 17th-round roots into a decent-fielding SS with decent-looking hit tools, but he has had some kind of injury every year in the minors since being drafted and also got suspended for starting a brawl earlier in 2030. I think, "Heh, I'm getting a promising, nearly ready starting pitcher for these backup types?" and pat myself on the back for being so much smarter than the AI before trading, oh, let's see, how about, um, Wade for Talley--Wade seems destined to be injury prone and an attitude problem, and he'll probably have to move off SS sooner rather than later, while Stufi is a much better fielder and all-around nicer guy. Thanks, Arizona...suckers.

So, yeah, long story short, Doug Talley gives me a couple of decent years in the rotation in his pedestrian career (his best years would be with Washington after I traded him--for more starting pitching depth, naturally); Pascual Stufi becomes a fan favorite for the White Sox, winning multiple gold gloves as a solid supporting player on a couple of championship teams before petering out due to injuries; and Ron Wade, Mr. 17th Rounder, as they end up calling him, wins multiple MVPs for Arizona on his way to becoming a no-doubt, first-ballot Hall of Famer.

But that's not even the worst part...

In 2047, my White Sox met the Los Angeles Dodgers in the World Series. The '47 series would go down as perhaps the all-time greatest World Series ever played in my league: every game was a tense, low-scoring affair decided by 1 run, except for game 5, which was tied 1-1 in the 9th inning before the Dodgers won it with a walk-off 3-run home run. The Dodgers won game 1; we won game 2; the Dodgers won game 3; we won game 4; the Dodgers, as mentioned, won game 5; and we won game 6, setting up a winner-takes-all game 7. It was one of the most memorable game 7s ever, as the Dodgers' very first batter of the game hit a leadoff home run...and no other runs scored, giving them the 1-0 game 7 victory and the championship.

And who, you ask, hit that leadoff homer to win the game and series?

Why, Ron Wade, of course.