Originally written on Fangraphs  |  Last updated 11/20/14

Last week, I presented my list of the 10 best transactions of the off-season. Of course, if there’s a best, there also has to be a worst, so today, we look at the flip side of the winter maneuvers. I will note, however, that this list was harder to put together than last week’s version, as MLB teams are getting smarter and there simply aren’t as many total head-scratching moves made anymore. No one’s giving out Gary Matthews Jr or Barry Zito contracts these days. The biggest potential landmine of the winter was paying Kyle Lohse as if his ERA represented his actual talent level, and every team in baseball decided to pass on that kind of signing. So, while I don’t love most of the moves below, several of them are more defensible than moves in previous off-seasons. The worst moves aren’t as bad as bad as they used to be. Without further ado, on to the list. 10. The Royals acquire Ervin Santana. The Royals got out in front of the off-season, picking up Santana from the Angels on October 31st to ensure that they could get a durable pitcher with some bounce-back potential before the market exploded. The only problem is that the market for back-end starters didn’t explode. Other starting pitchers of similar value who did sign free agent contracts: Joe Blanton (2/15), Brett Myers (1/7), and Joe Saunders (1/7). Innings-eaters weren’t going for a premium this year, and if the Royals had waited, they could have gotten involved on the bidding for a better pitcher like Brandon McCarthy instead. By focusing on quantity of innings and cost certainty, they ended up paying far more than they needed to in order to acquire a guy whose main calling card is durability. 9. The Twins trade Denard Span for Alex Meyer. This trade ranked as my favorite off-season move from Washington’s perspective, and I’ll reiterate what I said about the trade last week: +3 win outfielders under team control for three seasons at a total of $21 million are worth far more than one low-level pitching prospect. If this was the market for Span, then the Twins simply should have kept him, allowed him to continue to show that he’s over his concussion issues, and marketed him as trade bait at mid-season, when contenders pay marked up prices to get talent for the stretch run. Meyer might turn into something special, so it’s not like this deal couldn’t work out for Minnesota, but Span wasn’t so expensive that the Twins couldn’t keep him, nor was he reaching a point in his career where he ceased to be useful to a rebuilding team. The fact that the Twins kept Josh Willingham, the oldest of their three outfielders, and shipped out the two younger center field options makes the decision even more curious. 8. The Royals sign Jeremy Guthrie for 3/$25M. All the things I said about the Ervin Santana acquisition apply here as well. I understand that Guthrie pitched well for the Royals after they picked him up from Colorado for a song, but his track record shows a pitcher in decline, and his success has hinged on an inconsistent ability to prevent hits on balls in play. Even if we grant that he’s likely better at hit prevention than an average pitcher, the rest of his game is still trending the wrong direction, and he projects out as a #5 starter over the next three years. #5 starters simply don’t require three year contracts. Even worse, the deal was backloaded into the future, as the team tried to fit Guthrie in under their payroll limit, so he’ll get paid the most when he’s likely a replacement level scrub in 2015. Had they not overpaid Santana, backloading probably wouldn’t have been necessary. 7. The Dodgers sign Brandon League for 3/$23M. The Dodgers have a lot of money. They’ve repeatedly shown that they’re not working against a tight budget constraint, so signing League didn’t cause them to have to avoid sign