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Heyman's Best-Ever Free Agent Deals

A few weeks ago Jon Heyman gave us his list of the worst-ever free agent signings, and you guys chimed in on what deals should have been included on the list.

Heyman is back at it again. This time, he has his list of the 20 best free agent signings ever. Topping the list is the 1-year/$1.25MM deal given to David Ortiz back in 2003. I am not convinced that a 1-year deal deserves to be at the top of this list.

So let's have it. Which deal would top your list? What deals not on the list, deserve to be included?

Cork Gaines writes for Rays Index and can be reached here.


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Braves signing Greg Maddux in '93. Best signing ever.

Lance Berkman @ $85M/7yrs (or $100/8 if option picked up) is a much better contract than Magglio or Vlad's $75M/5

I'm kind of surprised that Albert Pujols' 7 year, 100 million wasn't on there.

Pujols' deal was not a free agent signing.

Wow, that list is laughable, especially the back half. Hideki Okajima is the 19th best FA signing in history? Come on now.

What about 4-yr/$53M deal Randy Johnson signed in 1999 with the D-Backs? He won the Cy every single year of the deal, not to mention the '01 WS title.

Everybody forget about the sweet deal that the Red Sox got with Dice-K?

Approximately $8.7M per year over 6 years beginning with his age 26 season. And, he's been worth every penny since.

For those who may mention the $51.1M posting fee, that is not part of the contract, and we're talking strictly about contracts

That is a terrible list.

4. Barry Bonds, Giants outfielder, 1993; $43.75 million, six years.

Thats number 1 by far. Though the Maddux signing was damn good. He built them a stadium for gods sakes.

Okajima? More like Joke-ajima.

"Everybody forget about the sweet deal that the Red Sox got with Dice-K?"

Wow, is all I can say about this. One year into a contact pitching to a 4.4 era. That is straight non-sense. Why would one ignore the posting fee as well?

"Ortiz has done much more than that, and is probably a Hall of Famer based only on the half a career he's spent in Boston."

Cool so not only was it a 1 year deal but now apparently 5 solid seasons as a DH gets you in the HALL OF FAME now?

Hall of Fame players dont clear waivers early in their careers. This article is garbage

Awwww how quaint a person using era to discuss a pitchers effectiveness. Oh and congra-tul-ations on turning nonsense into a hypenated word.

Well they did mention Ichiro's posting fee in his contract. And it didn't cost $51 mil.

Ortiz went .288 31 HR 101 RBI in his 1st season in Boston. Was great for the money. But #1? Maddux got a few Cy Youngs and Won a WS in his deal.

And what about Carlos Pena's free agent deal last year? He got $800,000 and hit .282 46 HR 121 RBI

And actually ERA and WHIP show more in pitching ability then Wins. Everyone knows that.

These the best are FREE AGENT signings ever, not the best contracts ever. Pujols, Berkman, Dice-K were not free agents when they signed their current contracts.

I'm with you on that. For Ortiz to have a shot at the Hall he's going to have to get that 500 HR bench mark and I think that is going to be a struggle.
Heyman should stop making lists and start making cakes. But the cakes would require actual work and not this lazy garbage he's been slopping together about free agents...at the start of a season.
Thanks for playing Jon.

People, pay attention (ie, Wreckard), everyone's favorite baseball writer (outside of the genious that is Dayn Perry of course), Mr. Heyman lists Bernie Williams as a signing. So as far as I know Bernie only played for the Yankees, so yes, Pujols and Berkman and their cheap contracts (I'm talking relativity here) could be added to the discussion.

Also, how about Peavy? That's a pretty team friendly deal....

Wow. Darin, you are a gen-ius for telling other people to pay attention. Bernie Williams signed as a free agent with the Yankees THREE TIMES (assuming you count amateur signings, which I don't see any reason not to). Berkman and Pujols have never reached free agency, whereas Williams began his career as a free agent (i.e. undrafted) and reached free agency before being resigned twice during his Yankees tenure. Pay attention!

Peavy has also never been a free agent. Unlike the players on Heyman's list.

now I'm being flagged for "anti-spam"...this Type Key thing is rediculous.....

what I was trying to say, asm, is....I'm stupid.

Has anyone bothered to say Emil Brown, Oakland A's 2008??? He's tearing it up! And at 1.25 mil. Sheesh! Every single contender is going to be ringing up Mr. Beane asking about him come deadline time.

Yeah. Bernie was a great signing considering he was dead weight and couldn't play the outfield by 2004....

This proves that it's a lot easier to find the worst contracts than the best. I'd be interested to see Tim's list on this as oppose to well, anyone who writes for SI.

Does anyone remember when Andre Dawson, desperately interested in playing on grass, signed a blank contract with the Chicago Cubs and played for, as I recall, a half million dollars. He won an MVP and whacked 49 HR in a Cub uniform. Should be one of the top ten.

I like the Dawson comment. Pena's deal was amazing as well, probably better than Ortiz. I disagree that 1 year deals can't rank with the best, because they can often lead to team friendly deals down the road, as happened with Ortiz.

Vlad's deal was dirt cheap looking back at it, and he includes options. Given his age and production, he is worth twice that easy.

Dawson got paid 700k. I totally forgot he played with the Marlins.

Remember when the A's got Frank Thomas to play basically for free and he catapulted them from never-going-to-be's to within 4 games of a World Series appearance?

Nah that simply didnt happen because its a west coast team, nevermind.

He included the posting fees for Okajima and Ichiro, so you wouldn't be able to discount it for Dice-K.

As for the list, yes Ortiz being #1 is bogus, especially after seeing someone point out Pena's contract. Obviously, though, Pena is in Tampa Bay, and not Boston, so he is easily overlooked.

Jimmy Key being on this list is also stupid. Out of the 4 years he was in NY, he only had one season which he pitched more than 170 innings. He was good the first 2 years, but the last two he was injured and average. There have to be deals made in the past that were good for the length of the contract, instead of just half.

"Awwww how quaint a person using era to discuss a pitchers effectiveness. Oh and congra-tul-ations on turning nonsense into a hypenated word."

What if someone used BB and GB rates?

I sure would like to hear your opinion on the best signing than, dorfmac.

While Papi and Key led their respective teams to championships, Pena led his to last place in all major league baseball. I'm sure Heymen had that in mind when he made his list.

For me, it's hard to argue with either Papi and Maddux as #1, but one thing for sure - it's one of them.

Really? Papi is better than Bonds? C'mon. Just ... c'mon.

Ugh. I promised myself I wouldn't click on that list but I did. Where is Clemens to Toronto? 3 year deal, 2 (real, not Bartolo Colon) Cy Youngs? That wasn't better than Key?

"While Papi and Key led their respective teams to championships, Pena led his to last place in all major league baseball. I'm sure Heymen had that in mind when he made his list."

so you are saying that the Rays would have gone to the playoffs or even won the WS if they had the '03 Papi in their lineup?

Oh wait, they did have the '07 version of Papi and still finished in last. You think that maybe Papi may have had a little help?

That's actually not fair to Pena; he contributes a pretty solid glove at 1B as well.

I'm a little upset with this site for even linking to SI. The off the cuff responses make more sense than that garbage. Did Heyman run out of TP?

"Ugh. I promised myself I wouldn't click on that list but I did. Where is Clemens to Toronto? 3 year deal, 2 (real, not Bartolo Colon) Cy Youngs? That wasn't better than Key?"

No, he was in the twilight of his career.

“While Papi and Key led their respective teams to championships, Pena led his to last place in all major league baseball. I'm sure Heymen had that in mind when he made his list.”

…The RedSox didn’t win a championship in 2003 ~ they were the WC, and lost to the Yankees in the Championship series… Besides, he didn’t lead that team ~ that distinction goes to Pedro, or Manny, or Mueller, or Nomar or Varitek etc…

…And Key didn’t lead his team to a championship during the life of his contract either. In 1996, the 4th year of his contract, they did win the WS ~ but Bernie Williams, Paul ONeill, Andy Pettitte, John Wettland and multiple others have to be considered “leading” that team over Key who was like their 3rd-4th best starter. (Behind Pettitte and Cone while basically being a perfect clone of Rogers on the season)

wow
that list sucks.

Ortiz and Maddux well deserved. But Pena got snubbed, and it's because he plays in Tampa. Dawson is a good one too.

I really didn't like his worst ever signings list either. He said the Braves made a horrible decision on picking Hampton up, but they're not paying a huge chunk of that contract. And they got 1 or 2 pretty good years out of him til he got hurt. And then got hurt again. And then got hurt again.

But still, how can that be #1 over Barry Zito? At least Hampton never got moved to the bullpen, and he pitched in Coors. Zito pitches in a pitcher's park and got demoted to the bullpen. He can't top 85mph on a radar gun anymore. That's like paying $126 million for Jamie Moyer.

The David Ortiz deal is a good choice to have at the top of the list. To a sign a slugger like Ortiz for a just one million and a quarter, good move there by Epstein. To me, a deal that should be included is the Albert Pujols deal. Since signing the deal, Pujols has really come into his own and is now feared as arguably "the best hitter in the game." He signed for 7 years, $100 million. Some comparable players to Albert have received much more in recent deals. A-Rod at $275 million, Cabrera at $150+ million, sounds like Howard will ask for more than that $100 million, and even though he's not a hitter, do I need to mention the Barry Zio contract at $126 million? All these hitters just mentioned, Pujols puts up numbers almost identical, if not better than those hitters, yet his deal was only at the century mark. To me, Pujols gave the Cards a pretty team-friendly deal for what kind of a hitter and now defensive players that he is.

Yeah, I agree. Right now wit the way it's looking, Zito's contract would have to go down as the worst free agent signing ever.

Seriously, Heyman even mentioning the Braves in connection with Hampton was a joke. The Braves didn't pay him 2003-2005 and got ~430 innings of above league average pitching. In 2006 and 2007, insurance picked up the majority of the tab for Hampton's contract. The Braves had paid him less than $10 million total coming into this season . How is that not an amazing deal?

I would put either Maddux or Bonds at the top, but the Ortiz signing led to a lot of great things at a good value, as well as the two team-friendly deals he has signed since then. His impact on this Sox team has been nothing short of amazing. And to think, JD Drew gets paid more than he does right now. The Okajima signing shouldn't be on this list. While it was a smart, low-risk deal, I don't see how it could possibly make the top 20.

"No, he was in the twilight of his career."

Who cares if he was past the "twilight of his career", he was absolutely dominant in the 1997 and 1998 seasons.

NJM, it's a joke/reference. I guess you're not a Red Sox fan. Google that phrase.

Ahhh ... the Duquette joke. Flew right over my head.

(And Clemens still should have been on the stupid list.)

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