John Lester ... New 5 Year Deal

Great news from the Red Sox ... John Lester ... 5 years / $30 million.

Report: Extension for Lester - Extra Bases - Red Sox blog
FORT MYERS, Fla. -- According a Yahoo! Sports report by Jeff Passan, the Red Sox and Jon Lester have agreed to a five-year contract extension (pending a physical) worth $30 million with a team option for $13 million in 2014.

While Lester declined to confirm the report, the pitcher did tell the Globe that talks between his agent, Josh Yates, and the Red Sox had intensified in recent days, saying, "I know that the past couple days have been pretty good."

"I think it's in the process of hopefully at some point getting done," Lester also said, as he left City of Palms Park at 3 p.m. "I couldn't tell you when or what day."

Click to expand...

Great off season so far. We are extending the young core of this team, I like it.

Sounds like he undersold himself. Why do these Sox players do this? Not that I'm complaining.

Mossed81 said:

Sounds like he undersold himself. Why do these Sox players do this? Not that I'm complaining.

Click to expand...

The bird in the hand theory I guess.

Mossed81 said:

Sounds like he undersold himself. Why do these Sox players do this? Not that I'm complaining.

Click to expand...

It's a fair deal for both sides. Young players like Lester are still under club control for a good deal of time and they don't have much leverage anyway.

He could gamble like Papelbon, but a lot of things could happen over the next 5 years that make this extension look like a great deal for Lester. His arm could blow out or some other serious injury, he could revert back to the pitcher he was before 2008 with poor control and a league average ERA, or any other number of things that can happen to prevent him from pitching.

The worst case scenario for him now is that he potentially looses $20M over the next 5 years, a sum that he will more than make up for when he reaches FA the first time. The worst case if he went year by year is he'll be toiling in the minors or out of baseball in 3 years, with only $2M to his name.

He's 25 years old, and financially set for life. Today was a very, very good day for Jon Lester.

The Red Sox have signed ridiculously cheap deals with Lester, Pedroia, and Youkilis.

maverick4 said:

The Red Sox have signed ridiculously cheap deals with Lester, Pedroia, and Youkilis.

Click to expand...

The Sox have quietly done things like this to keep us in contention for many years to come

Mossed81 said:

Sounds like he undersold himself. Why do these Sox players do this? Not that I'm complaining.

Click to expand...

I disagree. He had a couple years of minimum left, and a couple years of arbitration.

Essentially all the redsox gained here, was the $13M option for his first year of free agency. He already was locked up. They gave him money upfront to save money on year 4 and 5. He probably wouldnt have made much more going year to year.

Foley said:

The worst case scenario for him now is that he potentially looses $20M over the next 5 years, a sum that he will more than make up for when he reaches FA the first time. The worst case if he went year by year is he'll be toiling in the minors or out of baseball in 3 years, with only $2M to his name.

Click to expand...

Jon Lester could be the best pitcher in the league for the next 5 years, and I doubt he gets $50m.


Even if hes a top of the line (without this deal), he makes 500K this year, $4M if hes lucky next year, $6M, $8M, $10M. Thats just under $30M if they go year to year.

What this does is the Sox take on a little risk, set up lester for life, and get year 6, his first year of FA, at a discount. They also get to start the AAV right now for luxury tax purposes. IE, Lester will count as $6M/yr for the next 5 years, instead of lower now and higher later. If Lester turns out, this gives them much more flexibility.

Synovia said:

Jon Lester could be the best pitcher in the league for the next 5 years, and I doubt he gets $50m.


Even if hes a top of the line (without this deal), he makes 500K this year, $4M if hes lucky next year, $6M, $8M, $10M. Thats just under $30M if they go year to year.

What this does is the Sox take on a little risk, set up lester for life, and get year 6, his first year of FA, at a discount. They also get to start the AAV right now for luxury tax purposes. IE, Lester will count as $6M/yr for the next 5 years, instead of lower now and higher later. If Lester turns out, this gives them much more flexibility.

Click to expand...

You're off a year. 2014 (year 6) would have been Lester's second year of free agency.

And players can make quite a bit in arbitration, or signing deals to avoid it. Two years ago Carlos Zambrano got $12.4M in his final year of arbitration. With inflation, Lester could have easily made $14M in his last year had he continued to pitch like he did in 2008.

Something around 500K in 2009, $5M in 2010, $9M in 2011, and $14M in 2012 seems more likely, looking at other players trends. Had Lester gone year by year he likely could have made at least $17M a year in free agency, bringing the total value to about 6/$62.5M. If Boston picks up the option, it will bring the total to 6/$43M.

This, of course, all assumes that Lester remains perfectly healthy over the next 5 years and continues to pitch like an Ace (it also assumes that Lester actually signs this extension). There is a potential for Lester to leave a lot of money on the table, but everything would have to go right in order for that to happen.

Foley said:

Something around 500K in 2009, $5M in 2010, $9M in 2011, and $14M in 2012 seems more likely, looking at other players trends. Had Lester gone year by year he likely could have made at least $17M a year in free agency, bringing the total value to about 6/$62.5M. If Boston picks up the option, it will bring the total to 6/$43M.

Click to expand...

Its possible, but I think 4-6-9 is probably more likely. Not that it would have gotten to that, the Red Sox don't let players they want get to arb...creates bad blood. Arb hearings aren't nice.


$17M, maybe. The Sox definitely save some money, but there is some risk assumed. Theres the opposite side too, Lester gives up some money, but is set for life. I don't think the deal is one sided by any means.

Synovia said:

Its possible, but I think 4-6-9 is probably more likely. Not that it would have gotten to that, the Red Sox don't let players they want get to arb...creates bad blood. Arb hearings aren't nice.


$17M, maybe. The Sox definitely save some money, but there is some risk assumed. Theres the opposite side too, Lester gives up some money, but is set for life. I don't think the deal is one sided by any means.

Click to expand...

Where are you getting these numbers, when there is precedent that he would get more? If Zambrano is worth $12.4M in 2007, Lester is worth more than $9M in 2012. And if Zito can get $18M per as a FA in 2007, Lester could easily make $17M per as a FA in 2013.

I doubt they'd go to an arbitration hearing either. If Lester wanted to go year by year I expect they'd settle on a contract before a hearing was necessary, like what they did with Papelbon, or like the Cubs did with Zambrano.

Globe is saying Lester got a one-year deal.. Still haven't agreed long-term.. I did read this morning where Lester said that the report was premature about his signing a 5-year deal..

Foley said:

Where are you getting these numbers, when there is precedent that he would get more? If Zambrano is worth $12.4M in 2007, Lester is worth more than $9M in 2012. And if Zito can get $18M per as a FA in 2007, Lester could easily make $17M per as a FA in 2013

Click to expand...

What a player gets as a free agent is in no way comparable to what an arb player gets.

Synovia said:

What a player gets as a free agent is in no way comparable to what an arb player gets.

Click to expand...

No kidding. Lester would have been a free agent in 2013 when he could have gotten $17M per.

"Lester could easily make $17M per as a FA in 2013"

Also, Zambrano wasn't under team control. He was offered arb as a free agent, not while he was still under team control.


The last deal comparable to Lester (in years left, etc) was Brandon Webb, who in today's money, got 4/26.

Foley said:

No kidding. Lester would have been a free agent in 2013 when he could have gotten $17M per.

"Lester could easily make $17M per as a FA in 2013"

Click to expand...

Right, but him being able to get 17M in 2013, which makes the HUGE assumption that he is still Ace-level at that point, and last year hasn't proven to be a career year, and he hasn't hurt himself.

But none of that affects his arb numbers. Look at players who are still under team control, with similar years, and similar performance, and they get almost no money for the first couple arb years.

Synovia said:

Also, Zambrano wasn't under team control. He was offered arb as a free agent, not while he was still under team control.


The last deal comparable to Lester (in years left, etc) was Brandon Webb, who in today's money, got 4/26.

Click to expand...

No, that's wrong. Zambrano earned the minimum in 2004, and then was under team control the next 3 years. In 2007, the final year of being under team control, he avoided going to a hearing and agreed on $12.4M.

As far as Webb, he signed an extension, and didn't go year by year. He left money on the table too.

Synovia said:

Right, but him being able to get 17M in 2013, which makes the HUGE assumption that he is still Ace-level at that point, and last year hasn't proven to be a career year, and he hasn't hurt himself.

Click to expand...

That the whole point. I said, several times, this is only relevant if he remains an Ace. If Lester is perfect for the next 5 years, he could have left $20M on the table.

My initial post, which you seemed to take issue with, was looking at the worst case scenario for Lester fiscally. Him remaining an Ace and and leaving money on the table is that worst case scenario.

But none of that affects his arb numbers. Look at players who are still under team control, with similar years, and similar performance, and they get almost no money for the first couple arb years.

Click to expand...

Not really.

Wang: $4M in his first arb year
Bedard: $7M in his second
Zambrano: $12.4M in his third

Each pitcher was coming of at least two very good years. Lets just use those numbers with no inflation. 500K in 2009, $4M in 2010, $7M in 2011, $12.4M in 2012. And $17M in 2013 and 2014 as a FA. That is still $57.9M over the next 6 years, just under $15M less than the $43M in the extension. When you do account for inflation, $20M is easily lost.

I think it's a good deal for both sides. Lester is going to get $6 million avg over the next 5 years. That's great for the Sox if Lester performs as he did last year. I see no reason why he won't perform well, since he's fully recovered from his bout with cancer. His struggles prior seemed to be from his weakened state. He sure wasn't throwing 95-96 when he first came up.