Worst Red Sox contracts ever

[chrisfont9]

No, Simmons claimed, after Renteria was traded after the 2005 season, that he hated the Renteria signing because Renteria was a guy who never scared him in the 2004 World Series. When it was pointed out that his feelings about being scared don't matter and in fact Renteria had batted 333/412/533 in the 2004 World Series and was in fact one of the few guys for St. Louis who actually showed up, he doubled down, got defensive, and ran away.

I like Simmons' podcasts for the most part, but his knowledge of baseball is not good and getting worse.

I appreciate the details on Renteria, I don't really remember him being injured, I just remember him seeming uncomfortable in Boston. There's an article about the trade to Atlanta where Bill Lajoie says the "adjustment period lasted longer than you had hoped." So in the eyes of the front office, it was more mental. I'm sure Sox fans did everything they could to make him feel comforable (extreme eye roll).

 

[Smiling Joe Hesketh]

Wasn't it DH3?

We don't talk about Bruno.

 

[Van Everyman]

 

[saintnick912]

It's no Panda or Rusney by a long shot, but: resigning Mike Lowell heading into 2008 went pretty badly: 3/37M for 2.1 bWar overall, and negative value the last two seasons. That deal had the weird quality of being clearly bad at the time and yet nobody could bring themselves to care, since he'd just taken home the WS MVP.

In the postgame of Game 4 in Denver, the mob of Sox fans behind the dugout started a "re-sign Lowell" chant. A cigar smoking JWH turned towards the crowd, looking genuinely surprised at this. Was that the year that ARod opted out? I wonder how that contract would have ranked in this thread.

What did we pay Sang-Hoon Lee?

I felt like it was a lot.

Not enough for the majestic mullet photos.

 

[trekfan55]

It's no Panda or Rusney by a long shot, but: resigning Mike Lowell heading into 2008 went pretty badly: 3/37M for 2.1 bWar overall, and negative value the last two seasons. That deal had the weird quality of being clearly bad at the time and yet nobody could bring themselves to care, since he'd just taken home the WS MVP.

The Sox were actually outbid by the Phillies, yet Lowell signed with the Sox.

His contract was not good, but the injury that basically finished him off was the deciding factor. I still remember him being thrown out at 1st and not even be in camera range yet. Or at least once being put out at 1st from the OF.

 

[Mueller's Twin Grannies]

Best Sox contact might have been Wakefield's last deal.

Mount Rushmore of worst deals (Henry and Co. era) are Sale, Sandoval, Crawford, and Schilling's last contact (zero return on investment in 2008).

Dark horse to later supplant one of the above: Barnes.

 

[catsooey]

Ditto on Panda. Also, let's not forget Rusney Castillo, paid $72.5M to not play for the team at all. Well, "not play" may be a slight exaggeration, but a career WAR of 1.6 is pretty sad considering the cost.

Panda edges out Hanley in the “Obviously awful contract at the time” competition.

Carl Crawford could have reasonably continued to hit around .300 with some pop, good defense, and a ton of triples and stolen bases.

Hanley Ramirez could have reasonably continued to be a great hitter while being a passable defender.

Pablo Sandoval could have reasonably continued to be an above average third baseman while being a fan favorite, despite his size.

Panda was the absolute worst. I don’t know how that happened - he was being booted off his own team for his uncontrollable eating, and he refused to accept a weight clause in his contract. He couldn’t play or hit, and his poor belt. So of course the Red Sox do what no other team would do and inexplicably sign him to a huge contract with no strings attached (unless we’re talking about string cheese). If I can see something is a blatantly bad deal a mile away, then it’s a really bad deal.

This is after they ran their homegrown ace out of town with an insulting offer of 50% of his value. Luccino then did a media tour talking about how 70 million is “a lot of money” and that no pitcher over 29 is worth a decent contract. We then proceeded to watch John Lester pitch as an ace for the Cubs who won the series not long after. I still hate Larry Luccino.

*Baseball stuff aside, I hate his insistence on the fake pronunciation for his last name, so it will be less “Italian“ sounding I always suspected.

Hanley was bad and also totally preventable. He was known to be a flake and kind of a con artist who would say anything too get what he wanted. And his options were limited, so I don’t know why Cherington gave him the big contract.

And then there’s Rusney. They got outbid on the player wanted, so they threw all their money at the next one. 150 million (half went to Castro) without even knowing if he could play in the big leagues.

So I think Panda, Hanley, and Rusney were the worst, with John Lester being a bad decision in reverse - a gift that was thrown away.

 

[Rovin Romine]

So many fascinating theories that appear to be completely ungrounded in reality. But good for this:

"Castro, I think he was the worstest."
a poem by Catsooey

The absolute worst. I don’t know. . .
Booted off his own team
for his uncontrollable eating,
he ran his homegrown ace out of town;
did a media tour
on the fake pronunciation
for his last name,
(so it will be less “Italian“ sounding
I always suspected).
He was bad and preventable,
a flake and a con artist
who would say anything too
get what he wanted. And his options
were limited. They threw
all their money at Castro
without even knowing if he could play
in the big leagues. So I think
he was the worstest,
a bad decision in reverse -
a gift that was thrown away.

 

[CarolinaBeerGuy]

Panda was the absolute worst. I don’t know how that happened - he was being booted off his own team for his uncontrollable eating, and he refused to accept a weight clause in his contract. He couldn’t play or hit, and his poor belt. So of course the Red Sox do what no other team would do and inexplicably sign him to a huge contract with no strings attached (unless we’re talking about string cheese). If I can see something is a blatantly bad deal a mile away, then it’s a really bad deal.

This is after they ran their homegrown ace out of town with an insulting offer of 50% of his value. Luccino then did a media tour talking about how 70 million is “a lot of money” and that no pitcher over 29 is worth a decent contract. We then proceeded to watch John Lester pitch as an ace for the Cubs who won the series not long after. I still hate Larry Luccino.

*Baseball stuff aside, I hate his insistence on the fake pronunciation for his last name, so it will be less “Italian“ sounding I always suspected.

Hanley was bad and also totally preventable. He was known to be a flake and kind of a con artist who would say anything too get what he wanted. And his options were limited, so I don’t know why Cherington gave him the big contract.

And then there’s Rusney. They got outbid on the player wanted, so they threw all their money at the next one. 150 million (half went to Castro) without even knowing if he could play in the big leagues.

So I think Panda, Hanley, and Rusney were the worst, with John Lester being a bad decision in reverse - a gift that was thrown away.

Considering he uses the Italian pronunciation for Lucchino, I suspect your anger is misguided.

 

[Marceline]

The 91 free agent contracts to Jack Clark & Matt Young still make me wince. Crawford and Panda are for me the most recent debacles.

I feel like we need a version of OPS+ for contracts - adjusted for era by average salary/payroll at the time. Value below replacement contract or something similar. It's really tough to compare a Matt Young type deal to some of the more modern contracts.

 

[catsooey]

Considering he uses the Italian pronunciation for Lucchino, I suspect your anger is misguided.

No. No, no, no, no. Not true. Italian pronunciation? Pfft!
Did I say anything about how ‘some’ people in Italy might pronounce it? I don’t remember that….
Please don’t take away reasons for me not to like Larry Luccino

 

[catsooey]

So many fascinating theories that appear to be completely ungrounded in reality. But good for this:

"Castro, I think he was the worstest."
a poem by Catsooey

Actually, the original was a poem. Jokes on you.

 

[Philip Jeff Frye]

Mount Rushmore of worst deals (Henry and Co. era) are Sale, Sandoval, Crawford, and Schilling's last contact (zero return on investment in 2008).

Dark horse to later supplant one of the above: Barnes.

A month after this post, Barnes is looking like less and less of a dark horse.

 

[Mueller's Twin Grannies]

A month after this post, Barnes is looking like less and less of a dark horse.

Yeah, I think he's supplanted Schilling at this point.