Was Hamilton worst free-agent signing of all time?

Poor Josh Hamilton. He might have been freed from captivity in Southern California, but he goes right to the top of a list nobody wants to join:

The Worst Free-Agent Signings of All Time.

And trust me, that’s a tough list to top. But here is my new, updated, post-Josh-a-palooza top five, with a few honorable mentions thrown in there for your second-guessing consideration:

1. Josh Hamilton (5 years, $125 million)

OK, I know what you’re thinking: Was he really that bad -- bad enough to rank above the others on this list?

Well, I’ll concede that the guy did have a 21-homer, 32-double season in his first year with the Angels. And his 3.0 Wins Above Replacement over two seasons tops the total value of nearly every other player I considered for this prestigious honor.

But the Hamilton deal gets massive extra credit for its messy ending alone. His team didn’t just eat more than $60 million to make him go away. The Angels were so desperate to get him off the premises that they were willing to “trade” him for pretty much nothing -- to a team in their own division. Amid a bizarre backdrop of embarrassment, frustration and (let’s face it) anger. So, in the end, they paid him over 100 million bucks for, well, what exactly?

2. Mike Hampton (8 years, $121 million)

When you mention a signing and people just start laughing, you don’t need to know much else. But holy schmoly, was this guy ever a debacle for the Rockies.

Went 21-28, with a 5.75 ERA. Was worth minus-1.7 WAR pitcher. Was even lousier on the road (9-19, 5.77) than at Coors (12-9, 5.73). No word on what his kids thought of the Colorado school system that he found so attractive.

But the true measure of what a nightmare this contract was is this: When the Rockies finally figured out a way to trade him, they had to finagle a way to have three teams chip in to pay him for the next six years -- including a team he never threw a single pitch for (the Marlins). This wasn’t only disastrous; it was historically disastrous.

3. Melvin Upton Jr. (5 years, $72.25 million)

On one hand, I’m not sure it would even be possible for any team to get less return on (ahem) the largest contract in franchise history than the Braves got from B.J./Melvin over the last two years. After all, do you know how challenging it is to unfurl two consecutive seasons with a batting average under .210, fewer than 15 homers and more than 150 strikeouts? It is so challenging that nobody else in the history of baseball has ever done it. How 'bout that?

On the other hand, I did feel compelled to give the Braves a slight break here because they somehow pulled off the impossible: They found a team (i.e., the Padres) willing to take on every penny of the last three years of the contract. But the bad news is, they had to trade Craig Kimbrel to do it! So that was fun.

4. Manny Ramirez (2 years, $45 million)

I keep grasping for the perfect word to describe Manny’s free-agent deal with the Dodgers in 2009. Does “scam” work? How about “swindle”? Possibly “hustle”? Or, as one friend of mine suggested helpfully, “fraud”?

Whatever it was, “disaster” doesn’t quite seem adequate. One minute, he was the most lovable Dodger on Earth after the 2008 trade with the Red Sox. The next, he’d managed to charm them into that contract, only to get suspended a month into the next season for using (gulp) a female fertility drug. And then, for some reason, he wasn’t the same player. That didn’t stop him from collecting $8.333 million a year from the Dodgers for three years (yeah, really) after they’d dumped him on the White Sox. What a beautiful, heartwarming tale.

5. Chan Ho Park (5 years, $65 million)

I had so many juicy options for the final spot on this list. You’ll be seeing them in the honorable mention section momentarily. But when I revisited Chan Ho’s glorious Rangers career, back in 2002-05, it was a powerful reminder of just how big a horror show this contract actually was.

Here were Park’s year-by-year ERAs in Texas: 5.75, 7.58, 5.46, 5.66. Here were his year-by-year WHIPs: 1.59, 1.99, 1.44, 1.68. He made 68 starts for the Rangers. Exactly 24 of them were quality starts. And all this came while he was one of the 10 highest-paid players in the entire sport, remember.

So while it’s Tom Hicks’ infamous A-Rod contract that still makes people in Texas break out in hives, the Chan Ho deal was way worse. We wouldn’t want you to forget that or anything. So here he is on this exalted list. He can thank us later.

Top five honorable mentions:

Carl Pavano (4 years, $39.9 million with the Yankees): It wasn’t all his fault that he missed 106 starts in four years. But he had a 5.00 ERA in the starts he didn’t miss!

Jason Bay (4 years, $66 million with the Mets): Hit.234/.318/.369 as a Met. But hey, he did average nearly seven home runs a year.

Chone Figgins (4 years, $36 million with the Mariners): Hit .227 as a Mariner, with a 68 OPS-plus and minus-0.9 WAR. Yikes.

Gary Matthews Jr. (5 years, $65 million with the Angels): Had a minus-.6 WAR over these five years, if you count the part in which he finished up Year 5 with the Mets. Hard to do, folks.

Andruw Jones (2 years, $36.2 million with the Dodgers): For one horrendous season, he's tough to beat. Hit .158 for L.A., with three homers in 258 plate appearances.

Just missed this list: Jason Schmidt, Barry Zito, Denny Neagle,

Special international incident citation: Kei Igawa.

Disaster in the making: Shin-Soo Choo.

Category unto himself: A-Rod.