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 signing a better player at another position. However, throwing $23 million at League still looks awfully silly, given that the market for relief pitchers never really took off either; the only reliever to get more guaranteed dollars this winter was Rafael Soriano. Mike Adams signed for half of what League got in total dollars. Jason Grilli and Joel Peralta will make in two years what League will make in one. Koji Uehara signed for $4 million. Brandon Lyon signed for less than $1 million. There was just no need to give Brandon League a three year contract, whether the Dodgers can afford to absorb mistakes like that or not.

6. The Twins sign Kevin Correia for 2/$10M.

There is a place in baseball for a pitcher like Kevin Correia. He throws strikes, gets some ground balls, and can be reasonably relied on for 150 not-completely-horrible innings. However, that place is as a #5 or #6 starter on a team that needs rotation depth to ensure that some young kid doesn’t pitch them out of the playoffs. For a rebuilding team with no real hope of contention in 2013, Correia offers little of value. He’s taking the rotation spot that could have been given to another pitcher with actual upside, who might turn into someone the team could get value from long term, and worse, because they gave him a two year deal, he’s now taking up payroll space that could have been spent on a legitimate upgrade at another position in 2014. Why the Twins let Scott Baker go, only to replace him with Correia at a higher price, is one of the mysteries of the winter.

5. The Diamondbacks trade Chris Young for Cliff Pennington and Heath Bell.

The Diamondbacks clearly wanted to change their culture, and had no interest in bringing Young back to Arizona for the final year of his contract. Cliff Pennington is actually a decent role player, and acquiring him in the process gives them some needed infield depth. However, this trade is still just silly. Whether they liked his personality or not, Young is still a above average center fielder who can destroy left-handed pitching and hold his own against righties, and turning that into a utility infielder and an overpaid setup man is just simply a downgrade in talent. It’d be one thing if they had turned Young into Pennington and then used the cost savings to make a real upgrade elsewhere, but Bell’s salary basically offsets the savings, and then they replaced Young in the outfield with a worse version of the same skillset, as seen in the next move on our list.

4. The Diamondbacks sign Cody Ross for 3/$26M.

Like Young, Ross has a large career platoon split, doing most of his damage against left-handed pitchers. Unlike Young, Ross can’t also play center field, and instead of having a lefty mashing outfielder under contract for one year, they had to give Ross three to sign as a free agent. Meanwhile, the similar skilled Scott Hairston got $5 million total over two years from the Cubs. There’s a reason Cody Ross had to settle for $3 million on a one year deal from the Red Sox last winter; he’s just nothing special, and that the D’Backs shipped out Young in order to make room for the opportunity to overpay Cody Ross just confounds all the more.

3. The Mariners trade John Jaso for Michael Morse.

The Mariners badly wanted to improve their offense this winter. Considering how problematic run scoring has been for them the last few years, that was a noble goal. Here’s the problem, though: this trade very well might make the offense worse, while also downgrading the defense at the same time. While John Jaso is coming off a career year that he likely won’t repeat, he has a career 116 wRC+ in over 1,000 big league plate appearances, making him the best hitter the Mariners had in the organization, and one of the best hitting catchers in baseball. However, the Mariners don’t like his defense behind the plate and he doesn’t have the power of a typical DH, so the organization simply didn’t value him very highly, and shipped him out for a 1B/DH that they’re going to let wander around left field. The catcher defense argument begins to fall apart when you realize that trading Jaso means that Jesus Montero is now the team’s starting catcher, and that the position opened up by not DHing Montero anymore will be filled by giving Justin Smoak another shot as a full-time first baseman. Shipping out Jaso to create a job for Justin Smoak offsets the offensive gain Morse might provide, and the realignment crushes the defense in the process. Oh, and Morse is a free agent at the end of the season, while Jaso had three years of team control remaining.

2. The Royals trade Wil Myers, Jake Odorizzi, Mike Montgomery, and Patrick Leonard for James Shields and Wade Davis.

James Shields is a good pitcher. Wade Davis might be a good pitcher, maybe. Both are signed to below market contracts, though Davis’ isn’t so team friendly if the conversion back to the rotation doesn’t work. However, the price the Royals paid to acquire these two starters was simply too high. Myers should have been the Royals starting right fielder, but by losing him in the process of acquiring pitching upgrades, the team has to give a replacement level scrub a full time job again. And, unfortunately for Kansas City, this kind of future-value-for-present-value swap seems unlikely to pay off, as there’s still a vast gulf between the Tigers and the Royals in the race for the AL Central title. If everything breaks right, the Royals might have a shot at one of the two wild card spots, but even that seems like a longshot, given how many AL teams are pushing their chips into the pile this year. This trade significantly devalues the Royals future, all for the reward of making them the eighth or ninth best team in the AL this year. There’s a time to punt the future and go all-in. The Royals weren’t there yet. This trade makes it less likely that they’ll be there any time soon.

1. The Marlins blow up their team again.

You can make an argument for the moves the Marlins made this winter. Eno Sarris already did, actually. They shipped out a lot of talent and a lot of payroll, and if you believe that they’re going to be able to reinvest the funds freed up by losing the contracts of Jose Reyes, Mark Buehrle, et al, then the Marlins might actually be better off long term with a glut of young players and a bunch of payroll flexibility. The problem, of course, is that payroll flexibility is only useful if it leads to players signing with your team. Given that the Marlins just gave the entire city of Miami the middle finger one year after their new stadium opened, and that they’ve angered their franchise player in the process, there’s no reason to think that premium free agents are going to be lining up to sign with the Marlins while Jeffrey Loria still owns the franchise. Their free agent haul this winter? Juan Pierre, Placido Polanco, and Chone Figgins. These are the kinds of players who will take Miami’s money. Instead of expecting the team to reinvest their savings into the product, we should expect the Marlins to do what the Marlins have done for most of Loria’s ownership; line the pockets of ownership with large profits while putting a bad baseball team on the field.