Red Sox and Large Contracts, Historically

There've been a couple disasters (Sandoval, Crawford, Castillo) and a couple other "meh" in here (like Renteria didn't quite work out but not really in a way that was harmful), but overall that's a pretty damn good list of baseball players.

The usual typical reaction is cool we got a new toy, something interesting to talk about.

I think that's the case with most of the names on the list. We try to justify it in our minds but worry about the reservations that come attached with the player.

Some were obvious problems waiting to happen from go. Yeah happy to have Sandoval. He should be better than Middlebrooks was and has been a big game player and even batted .330. Just hope he doesnt self combust at homeplate. Stuff like that. What could go wrong with Rusney "the answer to Abreu" Castillo?

Some had serious injury concerns attached. I mean was Sale not second guessed immediately except for me thinking Duquette was getting a lower annual value and shorter deal to account for his obvious TJ need.

Some of these guys certainly werent worth the money as far as the WAR/$ value goes but they contributed to champion Red Sox teams of our lifetime. I understand their flags fly forever guys and strict numerical guys thinking they can just about squeeze efficiency out of just about everything. For me I dont care that Keith Foulke or Victorino or Lackey or even freaking David Price didnt live up to the totality of their values. They directly contributed to memories that will last my lifetime and even those of the guys who paid for them depending upon whether winning championships or generating the biggest profits floats their boats.

Some of the guys...well Soto was a trade, bit a free agent, but the excitement that the Yankees fans feel for Soto was how I felt when Manny came aboard.

Some of these deals were legacy deals so I dont have an issue with them. Hardly think Varitek bankrupted them and they would have had better options. They got 3 productive seasons out of him before the bat died. No regrets about Pedroia. The dude should never be in a uniform other than the Sox. Glad he stuck around long enough to get a 3rd ring.

Some were obvious disasters from go like Crawford,like Hanley's return and shift to LF of you were being honest with yourself. We knew Gonzalez had shoulder issues and Drew misses games.

All in all I dont think they did too badly over the years.

At the time it was the fourth largest contract extension in history or so says this article.

syndication.bleacherreport.com/amp/674378-adrian-gonzalez-and-the-10-largest-contract-extensions-in-mlb-history.amp.html


It started off very good with that monster 2011. He was still so good in 2012, that the Dodgers gave up legit prospects and took Crawford and Beckett in order to acquire him. He also did play well for a lot of that contract though he was ultimately released.

I’m sure you know all of that, but I do remember that he was seen as one of the best players in the game at the time. And the Red Sox certainly didn’t regret the extension in that it freed them from other bad contracts, which in turn allowed them to build a World Series winner.

Very interesting list, and has been said...some clunkers. But I'm sorry, it is time to start thinking big once again. Yamamoto and Montgomery will cost, a lot, but it needs to done.

That's a great list and kudos to lronhoyabembe for compiling it. I wondered why the GOAT was missing but quickly realized that deal came prior to the '98 season after DD acquired the GOAT from Montreal, so too early for this list.

I think you can break the list down like this:

The Gold Club. We'd do it again.
Ramirez (based just on on-field performance)
Damon
Foulke
Varitek
Ortiz
Lester
Pedroia
JDM
X

Flags Fly Forever
These guys provided value for only a portion of their contracts, but contributed mightily to rings.

Dice-K
Drew (His slam in game 6 of the '07 ALCS was worth the $70M IMO. As you can tell, I'm a big believer in FFE.)
Lackey
Price
Porcello
Buccholz (Cy Young bound in '13 before he got hurt and he gave us some valuable, gutsy innings in the ALCS and WS.)

Disasters. Call FEMA.
Lugo (The money and years weren't huge, but he produced -.3 B-Ref WAR during the four years.)
Crawford (I confess that I loved the signing at the time.)
H. Ramirez
Sandoval
Castillo
Sale

Still pending
Story
Yoshida
Devers

Yoshi and Story are likely to produce some value during the time left on their contracts, but I wish we weren't carrying either one. I'm not crazy about the Devers deal but not losing sleep over it either. I love Raffy and ~4-WAR players aren't nothing.

Others
Renteria and A-Gon didn't provide much to the Red Sox but the organization moved on quickly from each of them in trades that worked out nicely. They got Andy Marte for Rent and flipped Marte for Coco Crisp. Handing A-Gon to the LAD made it possible to get rid of Crawford and Beckett. Moving all that salary set up BC's incredible 2012-'13 off-season and the 2013 championship.

Beckett (I think he's missing from the list) also falls into the Others category.

Whitlock's contract doesn't fit nicely into any category above but it's so team friendly that it's impossible not to like it. Eo's deal was YMMV.

Nitpicky here but I'd move JD Drew up to the top tier. 

Beckett is indeed missing; I hadn't forgotten about him but I missed that he actually signed 2 extensions with the Red Sox. The first was for three years and $30MM, which missed the cutoff for the list. The second one came in 2011 and was for 4 years, $68MM

edit: I added Beckett to the table.