On Wednsesday, I gave my thoughts on the 10 moves from this past off-season that I liked the most. Today, we’ll look at the other side, and cover the 10 moves that most made me scratch my head.

10. Phillies sign Marlon Byrd.

Cost: Two years, $16 million.

$8 million per year for a guy coming off a +4 WAR season would ordinarily have no shot at ending up on any kind of list of the winter’s worst moves, especially given the short term of the deal and the limited risk that the overall expenditure implies. That said, it isn’t often that a guy goes from -1.0 WAR and a PED suspension at age-35 to +4 WAR at age-36, and so the question is simply how much should we put into one excellent season versus what Byrd had done previously. We had over 4,000 plate appearances showing Byrd to be an average hitter, and now we have 600 where he’s been an excellent hitter. Maybe he found a late career miracle cure and is going to ride his new found success to glory, but more likely, he’s going to go back to being Marlon Byrd, and the Phillies are going to remember why they gave up on him a decade ago.

9. Yankees sign Carlos Beltran.

Cost: Three years, $45 million.

Beltran is still a really good hitter, and in 2014, he’ll probably earn his $15 million paycheck, even if he’s now more of a DH than a regular OF. But Beltran is going to be 37, and it won’t be long until he’s exclusively a DH, and the bat isn’t so good that he can afford to slip much and still be an impact player without adding anything in the field. And his age, slippage has to be expected, and $15 million for a 38 or 39 year old Beltran probably isn’t going to look very good. On a one or two year deal, this could have made sense, but for $45 million over three years, the Yankees could have done better.

8. Colorado acquires Brandon Barnes and Jordan Lyles.

Cost: Dexter Fowler.

I get that the Rockies have outfield depth, and wanted to give guys like Corey Dickerson and Charlie Blackmon a shot, and Fowler’s getting expensive enough in arbitration where he’s not some kind of massive bargain anymore. However, he’s still a quality player, in the prime of his career, and the Rockies basically gave him to the Astros in order to free up enough room in the budget to sign Justin Morneau, who is older, worse, and not really much cheaper. Moving Michael Cuddyer to first base would have freed up playing time for Dickerson or Blackmon in the same way that trading Fowler did, and the team would have been better off for it. Lyles and Barnes are unlikely to ever make any real contribution in Colorado, and it’s hard to see this series of moves actually paying off for the Rockies.

7. Diamondbacks sign Bronson Arroyo.

Cost: Two years, $23 million.

Bronson Arroyo is unoffensive. He’s not bad, and when he keeps the ball in the ballpark, he can even look deceptively effective. But the reality is that Arroyo turns 37 in a week, gets destroyed by left-handed batters, and his entire success is based on walking the tightrope of weak contact. If he doesn’t hit his spots perfectly, 2011 happens, and he threatens the all time record for home runs allowed in a season. Arroyo is an okay back-end starter, but there’s no good reason to spend $12 million per year on okay back end starters, especially for an organization with a limited payroll and younger kids who project to be nearly as good. Arroyo’s biggest selling point is his durability, but 200 mediocre innings just aren’t that valuable.

6. Diamondbacks acquire Addison Reed.

Cost: Matt Davidson.

I don’t mean to pick on the Diamondbacks, but I actually like this trade even less than I like the Arroyo deal, and I don’t think I hid the fact that I didn’t really like that deal too much. It’s not that Addison Reed is bad, because he’s not. He’s fine, and he’ll be a good enough closer for Arizona. But they already had J.J. Putz and David Hernandez, who also would have been good enough closers, and the D’Backs didn’t need a third good-not-great right-handed reliever enough to justify trading a player with some legitimate value. Even if they didn’t see Davidson as a long term piece to build around given their roster and his defensive skills, he’s still a property of some real value; Marc Hulet ranked him #62 on his Top 100, while Baseball America came in at #72. This isn’t a guy to just give away for a minor bullpen upgrade. To make things worse, Reed has racked up a ton of saves in his time in Chicago, and is going to be quite expensive to retain in his arbitration years, so this probably ends up being Davidson for a few years of Reed’s services before he gets non-tendered. And that’s not a good swap.

5. Mets sign Curtis Granderson.

Cost: Four years, $60 million.

I get that the Mets offense was lousy last year, and Granderson makes it less lousy, but for $60 million, you have to get more than what Granderson projects to give over the next four years. Both ZIPS and Steamer see him as roughly a +2 to +3 WAR player for 2014, and the reality is that left-handed hitting outfielders of similar value were signing for a fraction of what Granderson cost the Mets. He may be marginally better than David Murphy (2/$12m), David DeJesus (2/$11M), or Nate McLouth (2/$11M), but there’s no way the gap is worth $10 million per year, plus an extra two years committed for ages 35 and 36. Granderson is getting paid like an impact player, but he just isn’t one, and the Mets could have gotten 90% of the production for 15% of the cost.

4. Yankees sign Masahiro Tanaka.

Cost: Four years, $108 million, plus player option for another 3/$67M.

I think Masahiro Tanaka is probably going to be very good. This isn’t about being skeptical of his abilities, or his prior workload, or anything relating to Tanaka, really. This is all about the contract, and specifically, the opt-out. While Tanaka’s deal is widely reported as $155 million over seven years, the opt-out means that it’s really a contract for $88 million over four years, not including the $20 million posting fee, with some chance that the Yankees will have to pay Tanaka an additional $67 million if he goes bust. Essentially, the Yankees paid $27 million per year for the next four years if Tanaka is good, and if things don’t break in their favor, they pay a $67 million tax to boot. If they only wanted a four year commitment, they could have signed any two of the domestic free agents for the same amount that they paid to get Tanaka, upgrading their roster in a very similar manner while taking a tiny fraction of the risk. Without the opt-out, at least this would have had a chance of working for NYY. With the opt-out, the deal is all downside.

3. Rangers sign Shin-Soo Choo.

Cost: Seven years, $130 million.

$130 million isn’t superstar money anymore, but it should buy a better overall player than Shin-Soo Choo. The things he does well, he does very well, and they certainly have value, but he’s not a good fielder, he doesn’t hit left-handed pitching, and he doesn’t even have that much power for a guy whose value is almost entirely tied up in his bat. The total package is an above average non-star, and he probably was worth something closer to Curtis Granderson’s contract than the one he actually got. I thought the Giants overpaid for Hunter Pence, but he looks like the steal of the century compared to Choo’s deal with Texas. For the next year or two, Choo will be worth $20+ million per year, but the back end of this contract is going to be a disaster, and there just isn’t that much value at the front end; certainly not enough to make this contract anything but a mistake.

2. Mariners sign Robinson Cano.

Cost: 10 years, $240 million.

There’s a decent chance that, over the life of this contract, Cano actually is a $200 million player, and in terms of total wasted dollars, $4 million per year for a decade isn’t actually a huge mistake. If Cano had signed this same deal with another team, it probably wouldn’t have ranked this highly, but unfortunately for the Mariners, they are one of the organizations with the least to gain from signing the winter’s best free agent. For starters, they still aren’t particularly good even with him on board, so they’re unlikely to take advantage of the first few years of the deal where he’s likely to be worth his salary. Additionally, his signing displaced Nick Franklin, leaving one of the team’s better young players without a future in the organization. The Mariners needed a lot of things this winter, but a second baseman wasn’t one of them, and the upgrade they got from replacing Franklin with Cano — and whatever lesser thing they get for Franklin in trade — simply wasn’t the best use of their $240 million. By the time the Mariners are ready to win, Cano’s contract is likely to be an anchor, and the kind of big splash that looks regrettable not too long after the ink dries.

1. Tigers acquire Robbie Ray, Steve Lombardozzi, and Ian Krol.

Cost: Doug Fister.

There are basically two options here:

1. Everyone is wrong about Robbie Ray. The Tigers actually just acquired one of the best young left-handed pitching prospects in the game, the kind of guy who could step into their rotation in 2015 and provide years of quality innings before he ever makes any kind of real money.

2. Dave Dombrowski screwed up. Because if Robbie Ray isn’t a quality, high-end pitching prospect, the Tigers sold a pitcher as good or better than Masahiro Tanaka, who will make less than $20 million over the next two years, for the kind of return that a team should expect when trading a decent role player.

Pitching prospects are hard to predict, and there are plenty of scenarios where it turns out that #1 is actually true, and this deal works out for the Tigers. If Ray turns into something, swapping two years of Fister for six years of a good young arm won’t look like a bad idea at all, especially given the Tigers current pitching depth. But the consensus among other teams and prospect experts is that Ray is not that kind of prospect, and that this is the most lopsided trade we’ve seen in years. For two bargain years of Doug Fister, the Tigers should have gotten a really strong return, and very few people think this qualifies. Maybe Ray will prove everyone wrong. Or maybe a good GM just whiffed.