The Jon Lester contract situation

[sk7326]

It's been a while a700. I had to come back and dialogue at perhaps the biggest transitional time for the Sox since the departure of Pedro, Damon etc., after 2004. May not stick around but here's my 2c.

 

As you can probably predict, my stance is that trading Lester makes sense to me from a long-term strategic perspective. I don't think they should pay Lester market value for 5-6 years. I think top market value contracts for pitchers almost always ends up under-performing. It's hard to find counterexamples.

 

So I think there's a good possibility that they weren't going to resign Lester anyway for solid reasons. If that's the case then of course it makes sense to trade him for the best available pieces. Especially if they are out of the playoffs this year. Especially if Lester is pitching better than he ever has. Especially if a number of pretty loaded teams are in need of a starting pitcher exactly like him for a playoff run. All the factors seem to be aligning for a great haul.

 

Now, as for trading a top 10 pitcher for a #10 prospect--it's a good point but, like an optical illusion, it's misleading. Lester has been a top 10 pitcher for the past few years. Signing him as a top flight pitcher now is speculating that he will continue to be over the next 6 years, which is a different matter. History says he won't, and even if he does he'll cost a ton of money for that added value. Best case scenario the Sox break even. As for the prospects, they could get a very nice player, an everyday guy who any team would be happy to have. Maybe two of those guys. For 6 years each at almost no cost. Then there's the cost of the contract itself--maybe 24m a year.

 

The deal is basically:

Other team gets: Lester's next 6.5 years

Red Sox get: MLB-ready prospect or two and whatever $24m buys in 2015, 2016, 2017, 2018, 2019, 2020

 

From that perspective I think it makes sense without even knowing who the prospects are. Ideally it will be a batter with some pop.

 

That would leave them with a lot of money and a ton of prospects. They could deal for Stanton (partially supplied by whoever they acquire here) and still have a lot of depth to put around him.

 

All that said, it's painful to think of Lester pitching elsewhere. He's been a consummate professional and a big game performer. Hard to argue that he's been anything but positive for the Red Sox for his tenure there. I can see the argument that he deserves a lot of money for that--he does and he will get it. It just doesn't have to be paid by the Sox.

 

There is a lot of logic here which is good in a vacuum - the problem is when it gets applied to the marketplace, and 30 firms with 30 different revenue functions.

 

1. The Red Sox do not have the same fiscal constraints of other teams. If they place those shackles on themselves, it is entirely by choice. The value Lester (or anybody) provides does more for the Sox bottom line than it would in Tampa.

 

2. Jon Lester is very hard to replace because of both the quality and quantity of production. There is no way they can replace the quantity of production with one pitcher next season. Indeed, it is unlikely that any of their pitchers, regardless of age - will produce the innings value that Lester will provide in the next 3 seasons. He is basically one roster spot which has to be replaced by 2-3 pitchers in his absence.

 

3. You have to eat some suboptimal years to absorb a premium free agent. The question is what those years look like and can you live with that. With Lester, you'd probably get 3 years where he is more like (on average) 2012 Jake Peavy than a Cy Young contender. But that is 1200 innings of #2/3 starter production ... and in the way the market has evolved, that is probably worth $20-$25M a year fairly.

 

4. There is a possibility that this front office just does not believe in compensating players to that degree - which sounds good until you see what they are charging the public. It does not compute in a tolerable way.

[a700hitter]

It's been a while a700. I had to come back and dialogue at perhaps the biggest transitional time for the Sox since the departure of Pedro, Damon etc., after 2004. May not stick around but here's my 2c.

 

As you can probably predict, my stance is that trading Lester makes sense to me from a long-term strategic perspective. I don't think they should pay Lester market value for 5-6 years. I think top market value contracts for pitchers almost always ends up under-performing. It's hard to find counterexamples.

 

So I think there's a good possibility that they weren't going to resign Lester anyway for solid reasons. If that's the case then of course it makes sense to trade him for the best available pieces. Especially if they are out of the playoffs this year. Especially if Lester is pitching better than he ever has. Especially if a number of pretty loaded teams are in need of a starting pitcher exactly like him for a playoff run. All the factors seem to be aligning for a great haul.

 

Now, as for trading a top 10 pitcher for a #10 prospect--it's a good point but, like an optical illusion, it's misleading. Lester has been a top 10 pitcher for the past few years. Signing him as a top flight pitcher now is speculating that he will continue to be over the next 6 years, which is a different matter. History says he won't, and even if he does he'll cost a ton of money for that added value. Best case scenario the Sox break even. As for the prospects, they could get a very nice player, an everyday guy who any team would be happy to have. Maybe two of those guys. For 6 years each at almost no cost. Then there's the cost of the contract itself--maybe 24m a year.

 

The deal is basically:

Other team gets: Lester's next 6.5 years

Red Sox get: MLB-ready prospect or two and whatever $24m buys in 2015, 2016, 2017, 2018, 2019, 2020

 

From that perspective I think it makes sense without even knowing who the prospects are. Ideally it will be a batter with some pop.

 

That would leave them with a lot of money and a ton of prospects. They could deal for Stanton (partially supplied by whoever they acquire here) and still have a lot of depth to put around him.

 

All that said, it's painful to think of Lester pitching elsewhere. He's been a consummate professional and a big game performer. Hard to argue that he's been anything but positive for the Red Sox for his tenure there. I can see the argument that he deserves a lot of money for that--he does and he will get it. It just doesn't have to be paid by the Sox.

 

E1, good to see you. Stick around if you have some time. You make good points, and when I have some time tonight, I will put together a more thoughtful response. Keep in mind that young pitchers and prospects are just as likely to go down with an injury or underperform-- maybe even more likely. Of course the financila investment in them would be small compared to Lester. The one difference is that while Lester remains healthy, you know that you will be getting ace-like performance for a few more years. Prospects are just crap-shoots. I think the Sox have to start filling in the rotation with some young arms, but I also think they need one or two guys to build around. Lackey even with an extension should be fairly cost-controlled. Lester would be a big invesstment, but I think they could have raised the AAV and shortened the term to a reasonable 4 or 5 years. Reports are that they have made nothing beyond one nonserious offer. I think it is a mistake. TTYL.

[jacksonianmarch]

I honestly think a marquee FA pitcher contract is a success if the pitcher performs at ace level for half the contract. Due to the nature of the mechanics of pitching, you eat the risk of injury and decline. CC was effectively signed for 8 seasons. 4 of those yrs he was an ace. Last yr he was a #5 and this yr he's been an injured mess. The contract has been worth it, IMO

[Palodios]

I have tickets to tonight's game, and was hoping to see Lester pitch his last game with the Sox. Hopefully 2015 isn't a bridge year.

[jacksonianmarch]

The sox direction is puzzling. They wont titles three times based on strong pitching and timely hitting. They pawned off an unneeded piece in Peavy as they weren't re-signing him anyway. Understood there. But they aren't the Rays. They have cash to spend and one of if not the highest ticket prices in baseball. They aren't hurting for cash. That being said, they are in the process of selling off their ace and possibly their #2 and going all out rebuild in the rotation. Then, if they go out and sign an ace in the offseason, they'll be hypocrites with Lester. It is puzzling to say the least. Either they want the rebuild, and who knows how long that will take. Or they want to spend like a big market club and fill out their rotation, all the while looking like hypocrites with their home grown ace.

[sk7326]

The sox direction is puzzling. They wont titles three times based on strong pitching and timely hitting. They pawned off an unneeded piece in Peavy as they weren't re-signing him anyway. Understood there. But they aren't the Rays. They have cash to spend and one of if not the highest ticket prices in baseball. They aren't hurting for cash. That being said, they are in the process of selling off their ace and possibly their #2 and going all out rebuild in the rotation. Then, if they go out and sign an ace in the offseason, they'll be hypocrites with Lester. It is puzzling to say the least. Either they want the rebuild, and who knows how long that will take. Or they want to spend like a big market club and fill out their rotation, all the while looking like hypocrites with their home grown ace.

 

Sadly much true

[reYoukilis]

The sox direction is puzzling. They wont titles three times based on strong pitching and timely hitting. They pawned off an unneeded piece in Peavy as they weren't re-signing him anyway. Understood there. But they aren't the Rays. They have cash to spend and one of if not the highest ticket prices in baseball. They aren't hurting for cash. That being said, they are in the process of selling off their ace and possibly their #2 and going all out rebuild in the rotation. Then, if they go out and sign an ace in the offseason, they'll be hypocrites with Lester. It is puzzling to say the least. Either they want the rebuild, and who knows how long that will take. Or they want to spend like a big market club and fill out their rotation, all the while looking like hypocrites with their home grown ace.

I understand the strategy of not spending money and building within the farm system. I dont understand getting rid of Lester. Hes got a long track record of success with us and he wants to be with us. My thinking is that theyre going to try and deal Lester to a desperate team that are willing to give alot more than hes worth. Also if this rebuilding process is going to start from scratch, it may be a waste to keep Lester knowing that his best years will be spent on a team waiting for their prospects to get it together.

[Bellhorn04]

I honestly think a marquee FA pitcher contract is a success if the pitcher performs at ace level for half the contract. Due to the nature of the mechanics of pitching, you eat the risk of injury and decline. CC was effectively signed for 8 seasons. 4 of those yrs he was an ace. Last yr he was a #5 and this yr he's been an injured mess. The contract has been worth it, IMO

 

There's also a vesting option for 2017 which kicks in at $25 million unless he has a left shoulder injury in 2016. That would make it a 9 year deal.

[Palodios]

With Lester's scratch today, and trade talks heating up, things are getting real.

 

And for Lester more than anyone. Maybe now is the perfect time to throw out that last 120 million dollar offer and see where his heart is.

[St. Louis Carter]

The Cards, Dodgers, Brewers and LA are waiting with baited breath to see who gets Lester. He would push ANY of those 4 teams over the top.

 

The Cards are dangling Trevor Miller, Oscar Tavares and Allen Craig (reportedly) A pretty good coup for a rebuilding team.

Edited July 30, 2014 by St. Louis Carter

[Dojji]

The Cards, Dodgers, Brewers and LA are waiting with baited breath to see who gets Lester. He would push ANY of those 4 teams over the top.

 

The Cards are dangling Trevor Miller, Oscar Tavares and Allen Craig (reportedly) A pretty good coup for a rebuilding team.

 

That is horrible. Have you seen Craig this year? He's 30 years old next year and just fell off the face of the earth. That's a reclamation prospect you would pick up off the waiver wire, not something you trade your ace for. Even assuming he bounced back, he's not going to put the team on his back in the next 2 years, and I don't see the team coming together around him in that time, especially the starting staff. That and he plays a position we're already massively redundant in young players that we need to give playing time to. Or you could put him in the outfield where even if his bat does come back, he's nothing special.

 

Allan Craig is exactly -- EXACTLY -- the kind of player we don't need. I'd take a lesser deal in talent that was a better fit, over Craig, anytime considering where this team is right now. What have you guys got in the wings behind Matt Adams? Start talking about addressing areas where we can't replace our staff with high-potential young replacements and we can start to have a conversation.

 

As for the tagalongs, Miller is not a blue chip prospect, and Oscar Tavares is interesting but not enough to turn this trade into a good idea. Stay away Ben, you'd get more real value from the picks you'd get if he doesn't sign.

Edited July 30, 2014 by Dojji

[Palodios]

That is horrible. Have you seen Craig this year? He's 30 years old next year and just fell off the face of the earth. That's a reclamation prospect you would pick up off the waiver wire, not something you trade your ace for. And he'd be the centerpiece? No. Not even a little bit. Miller is not a blue chip prospect, and Oscar Tavares is interesting but not enough to turn this trade into a good idea. Stay away Ben

 

Oscar Tavares is regarded as the second best prospect in all of baseball. If he is on the table, Ben isn't asking around for other offers.

[d-money]

Cherington better hope these minor league prospects work out.I havent been impressed with De la rosa recently.

[Dojji]

Oscar Tavares is regarded as the second best prospect in all of baseball. If he is on the table, Ben isn't asking around for other offers.

 

Yes he is, if he's smart. If you don't at least pick up a half decent pitching prospect for Lester along with whatever else you get, you're going to regret it in 3-4 years. We really don't have that much pitching in the pipe, we can't get rid of Lester without setting up the future of the pitching rotation, unless you want that future to be De la Rosa 1, Doubront 2, Junk, Crap and Trash filling out the lower 3 slots.

[d-money]

That cardinals package is not enough for Lester

[d-money]

Do the mariners have any great prospects? Is seattle interested?

[Dojji]

Do the mariners have any great prospects? Is seattle interested?

 

No reason to think the Mariners would be in play for Lester at the deadline as they're 11 games out.

 

The offsseason may be another story but that has little to do with us at the moment.

[Palodios]

Yes he is, if he's smart. If you don't at least pick up a half decent pitching prospect for Lester along with whatever else you get, you're going to regret it in 3-4 years. .

 

Want me to go through the last crop of #2 prospects? Mike Trout, Mat Moore, Stephen Strasburg, David Price, Felix Hernandez, Longoria, Justin Upton. Taveras is insanely valuable, and Ben isn't going to get anything better than that.

[Dojji]

And then we trade for him and he turns into nothing.

[Palodios]

And then we trade for him and he turns into nothing.

 

Or we trade for pitching and that pitching turns into nothing. Or we trade for Stanton and he turns into nothing. See how this works?

[seabeachfred]

I have tickets to tonight's game, and was hoping to see Lester pitch his last game with the Sox. Hopefully 2015 isn't a bridge year.

 

There will be more than one bridge year Palodios if you want my honest opinion. Without an ace pitcher we are doomed until we get not only one but two game changers on the hill and I don't think Webster, Rubby, Barnes or Clay the Faberge Egg fit that description. Perhaps Owens and Renaudo could be those two. As far as the position players are concerned there is some duplication at key positions and the Red Sox must guess right and not pick the wrong guy in these spots.......catcher, shortstop, third base and center field. If they pick wrong and keep the weaker of the two we will be eating dirt for the next half-dozen years. What only our Yankee fans seems to understand is that if you sign someone for six or seven years and you get four solid ones from that particular player you have hit paydirt, especially if you get a WS Title out of it. Jacko mentioned the Yankees hurting over the CC signing NOW but overall they got their money's worth for four seasons and a WS Title to boot in 2009. If we could get another title from Lester it would be worth it IMHO.

 

One more point. The Red Sox are acting like a cheap mid-level team all of a sudden when they are among the richest teams in baseball, a totally loyal fan base that attend games and pays the highest prices in the land, a marketing extravaganza that puts millions into the coffers every year, a RSD travel program that sells out every season. There is no reason for the team to act like a bunch of tightwads. Yes, they made a mistake with that contract to Crawford in early 2011 but each case is different. Jon Lester has been a stalwart and dependable starter since we brought him up, save one bad season, and there is no reason he could not pitch effectively for another four or five seasons. If got a couple of pennants and a WS Title in that time the other two years of ineffectiveness (maybe, maybe not) would be worth it. I just think this is a very bad move.

[St. Louis Carter]

That cardinals package is not enough for Lester

Oh, I agree, but is there a team with more to offer? I don't know, just asking.

[Palodios]

Cards go for Masteron instead. Argument is moot.

[St. Louis Carter]

Cards go for Masteron instead. Argument is moot.

Afraid so. A ridiculous trade. An unproven AA player for a washed up starter. A f***ing joke.

 

Congratulations LA, SF, Mil or LA!!! Goddammit!

[Navafan29]

What is with these rumors that Lester might get traded to the Orioles for another pitcher? That's crazy.

[jacksonianmarch]

It's a great idea. Lester wont re-sign in Baltimore and in the meantime, the O's can kill off the Yankees chances of reaching the playoffs. Plus, you'll basically be guaranteed a shot at him in the offseason if you so choose, with no draft pick comp attached

[sk7326]

That is horrible. Have you seen Craig this year? He's 30 years old next year and just fell off the face of the earth. That's a reclamation prospect you would pick up off the waiver wire, not something you trade your ace for. Even assuming he bounced back, he's not going to put the team on his back in the next 2 years, and I don't see the team coming together around him in that time, especially the starting staff. That and he plays a position we're already massively redundant in young players that we need to give playing time to. Or you could put him in the outfield where even if his bat does come back, he's nothing special.

 

Allan Craig is exactly -- EXACTLY -- the kind of player we don't need. I'd take a lesser deal in talent that was a better fit, over Craig, anytime considering where this team is right now. What have you guys got in the wings behind Matt Adams? Start talking about addressing areas where we can't replace our staff with high-potential young replacements and we can start to have a conversation.

 

As for the tagalongs, Miller is not a blue chip prospect, and Oscar Tavares is interesting but not enough to turn this trade into a good idea. Stay away Ben, you'd get more real value from the picks you'd get if he doesn't sign.

 

Oscar Tavares was one of the top 5 prospects in baseball with comps to Vladimir Guerrero. For 2 months of Jon Lester that is a pretty phenomenal return. I also am certain that was never offered because the Cards are not stupid.

[d-money]

For who? Dylan Bundy?

[Station 13]

How many big pieces gets traded and sign huge extensions? Rarely. The Sox did it with Pedro a long time ago, giving him the biggest contracted ever for a pitcher. Today soon to be FA today won't do it. I also put Lester return to Boston at 50-50.

[d-money]

Cherington will look like a genius or a dumbass