When do we start thinking about trading away Jon Lester?

[Curll]

The current 4-game slide is hard to take. And while the division isn't exactly a powerhouse, the Red Sox would have to play around .600 for the rest of the season to win the division. The Mets are currently doing better than the Red Sox.
 
How much longer should the Red Sox hold onto hope? Lester could be a massive trade chip that could net the Sox a couple top tier prospects and help build around Xander, Pedroia, et al. 
 
At this point, dropping $100M+ on Lester seems like a sunk cost for 2014 and 2015 doesn't look fantastic with Napoli, Ortiz, and Lackey adding another year to their bodies.

 

[budcrew08]

Why would we? Guys like Pedroia and Lester are cornerstones for a franchise.

 

[chrisfont9]

I dunno, I still see him as a rare cornerstone player. This is 2012 all over again, guys vastly underachieving, masking a very solid core. Having Lester around for Victory 4.0 is probably prudent, depending on how high the bidding goes.
 
Also...
 

 
Pierzynski insisted he got a good jump and secondary lead. Replays suggested otherwise. He also appallingly put some of the blame on Victorino, who ended up tweaking his right hamstring busting it up the line.
“Vic made a good bunt,” Pierzynski said, “but it wasn’t perfect.”

Cut him. Cut him now.

 

[Curll]

Why would we? Guys like Pedroia and Lester are cornerstones for a franchise.

He's 30, a FA, and will cost about $120M to keep. 

 

[RedOctober3829]

He's 30, a FA, and will cost about $120M to keep. 

If you lose Lester your rotation would consist of 
 
--Clay Buchholz
--John Lackey
--Felix Doubront
--??
--??
 
That is not very promising with Buchholz and Doubront vastly underperforming and Lackey entering the last year of his contract.  Are you going to bring up two of the kids and plug them in?  If so, prepare for another season like this.  This team will not and should not let a player like Jon Lester go.  He is exactly the kind of player you try to keep.  

 

[rembrat]

The current 9-game slide is hard to take. And while the division isn't exactly a powerhouse, the Red Sox would have to play around .600 for the rest of the season to win the division. The Mets are currently doing better than the Red Sox.
 
How much longer should the Red Sox hold onto hope? Lester could be a massive trade chip that could net the Sox a couple top tier prospects and help build around Xander, Pedroia, et al. 
 
At this point, dropping $100M+ on Lester seems like a sunk cost for 2014 and 2015 doesn't look fantastic with Napoli, Ortiz, and Lackey adding another year to their bodies.

 
By all accounts those top tier prospects are already in the system.

 

[Snodgrass'Muff]

It depends on when you expect the next title window to be open.  If you think that window is open now, or is likely to be open within the next 2 or 3 years, you don't let Lester go.  If you think the team needs a heavy rebuild and might be 4 or 5 years from being competitive, you sell on Lester while you still can.
 
Personally, I think you'd have a very difficult case to make for this not being a team capable of winning another title in the next 3 years.  That's a very different thing than saying I think they are likely to win a title in that span, but even if 2014 ends up a lost year, a few solid mid-tier free agent pick ups this winter along with bringing back Lester, one solid starter emerging from Barnes, Ranaudo, Workman, Webster, de la Rosa, and Owens, or maybe a trade for a big bat (insert binky here), adding Betts and eventually Swihart to the roster, maybe Cecchini, and they are right back in the playoff hunt.  Maybe as soon as next season.  Never mind if they see a big name free agent they think is worth investing in.
 
There are a lot of paths that lead back to the playoffs, and many of them include Lester on this team.

 

[HurstSoGood]

I like Lester and think he fits well on this team and in this division. However, if the Sox are not going to be competitive in their offers to Jon, they should just trade him now. This team is not going anywhere. I am afraid that, come November, we will be having the same conversations about Lester (who inevitably signs elsewhere) that we had about Ellsbury, except we didn't just win the World Series.

 

[glennhoffmania]

By all accounts those top tier prospects are already in the system.

Yeah. If anything they should be trading prospects to fill a need. Dumping Lester doesnt solve any problems and most likely eliminates any chance of resigning him. And this season is far from over. It's not like any of the other AL East teams are all that scary.

 

[snowmanny]

If the Red Sox have a bad 2014 I think it increases the argument to sign Lester (assuming he continues to have a good year). I am confident this organization wouldn't plan on a long rebuild and losing Lester makes the hole they are digging out of much bigger. If they look like they have a strong core absent Lester then maybe they can work around losing him.

 

[jimbobim]

I voted for Trade Deadline try and salvage 2014 and that's what the overall sentiment appears to be. 
 
With some many assets and salary flexibility it makes little sense to give up before June. Acquiring an impact bat for OF is a necessity Ethier, Kemp, Denorfia, and more would theoretically be available. 
 
If one of those pickups doesn't help someone would bite on Lester for at least a top 5 prospect a pitching prospect and a recently drafted lottery ticket. ( Not endorsing just spitballing Ross Lester Gomes to Oakland for Norris and Gentry )  
 
A's get needed frontline pitching to compete against the Tigers Staff with a rotation led by Sonny and Lester making two starts a piece because kazmir and their backend sucks. Norris is a beast and steep pice to pay but Jaso is also pretty good. Angels would probably be interested as well. 

 

[EricFeczko]

I voted for Trade Deadline try and salvage 2014 and that's what the overall sentiment appears to be. 

Huh. We must be looking at completely different polls then. The sentiment in the poll I see appears to be at 50 percent.
 
 

With some many assets and salary flexibility it makes little sense to give up before June. Acquiring an impact bat for OF is a necessity Ethier, Kemp, Denorfia, and more would theoretically be available. 
 

 
The Dodgers need infielders, not a starting pitcher. There's no need to use Lester in a trade for Ethier/Kemp, when picking up salary/WMB/AAA pitching prospects would do just fine.
 
 

 
 
A's get needed frontline pitching to compete against the Tigers Staff with a rotation led by Sonny and Lester making two starts a piece because kazmir and their backend sucks.

 
SSS warning and red flags abound, but Kazmir has a 2.57 ERA/3.05 FIP this year.
 

If one of those pickups doesn't help someone would bite on Lester for at least a top 5 prospect a pitching prospect and a recently drafted lottery ticket. ( Not endorsing just spitballing Ross Lester Gomes to Oakland for Norris and Gentry )  

 
Oakland would be stupid to accept such a trade. As good as Lester may be right now, Norris and gentry are both cheap and effective.

 

 

[MakMan44]

You think that's a bad trade of the A's? Derek Norris has a wrong side platoon catcher up until this year and Gentry is a 30 year old back up OF. If that's what we'd be trading for Lester, I'd rather extend him or get the comp pick.
 
EDIT: And trading Lester in an effort to save 2014 is, quite frankly, stupid. Trading away your best starter when your 3/5 of your rotation is a mess doesn't make sense. 

 

[EricFeczko]

You think that's a bad trade of the A's? Derek Norris has a wrong side platoon catcher up until this year and Gentry is a 30 year old back up OF. If that's what we'd be trading for Lester, I'd rather extend him or get the comp pick.
 
EDIT: And trading Lester in an effort to save 2014 is, quite frankly, stupid. Trading away your best starter when your 3/5 of your rotation is a mess doesn't make sense. 

Derek Norris is a 24-yr old catcher with a career 110 wRC+. He's a young catcher with upside, who is currently showing it right now.
Craig Gentry has been used as a back-up, but is an excellent CF and an average hitter at the plate.
Oakland doesn't have a better catcher right now; Jaso makes Pierzynski look like Varitek behind the plate. Gentry provides cheap depth for their team. Finally, three fifths of their rotation are performing well (Gray/Kazmir/Chavez), while pomeranz makes a decent back-end starter. Giving up position player strength for an unnecessary and expensive pitcher would be an idiotic move by Oakland.

That being said, I completely agree that trading Lester is stupid. My point is that the trade is stupid for both teams, and therefore unrealistic.

 

[Hee Sox Choi]

You know who could use Lester?  
 
The Yankees.   :blink:

 

[Curt S Loew]

The current 9-game slide is hard to take. And while the division isn't exactly a powerhouse, the Red Sox would have to play around .600 for the rest of the season to win the division. 

And now it's 10.  But it's still May.  Way too early for this.

 

[Al Zarilla]

Derek Norris is a 24-yr old catcher with a career 110 wRC+. He's a young catcher with upside, who is currently showing it right now.
Craig Gentry has been used as a back-up, but is an excellent CF and an average hitter at the plate.
Oakland doesn't have a better catcher right now; Jaso makes Pierzynski look like Varitek behind the plate. Gentry provides cheap depth for their team. Finally, three fifths of their rotation are performing well (Gray/Kazmir/Chavez), while pomeranz makes a decent back-end starter. Giving up position player strength for an unnecessary and expensive pitcher would be an idiotic move by Oakland.

That being said, I completely agree that trading Lester is stupid. My point is that the trade is stupid for both teams, and therefore unrealistic.

Can you imagine the A's paying Lester anyway? If he had come up with them and pitched well, he'd be long gone from them by now, like with Zito, Mulder, Hudson, Gio G... 
 
Billy Beane and Bob Melvin are probably already starting to sweat, again, getting by the Tigers and Verlander though.

 

[Stitch01]

I'd probably rather sign him, but they should be accelerating the negotiating process if the losing continues for a couple of weeks. Make the best offer now, then market him if that isn't enough

 

[Bone Chips]

I think we already lost a substantial portion of the savings we should have gained from a hometown discount. Starting the negotiations too low really backfired. At this point I'd make one last best effort to sign him to a 5 year deal. If that doesn't pan out, wait till the height of desperation at the trade deadline and see if you can trade him for something more valuable than the draft pick you'd get.

 

[amfox1]

I'd probably rather sign him, but they should be accelerating the negotiating process if the losing continues for a couple of weeks. Make the best offer now, then market him if that isn't enough

 
They should start fielding calls to gauge his trade market and then they should start negotiating.  Keep in mind that, if he is not traded, the Red Sox will absolutely make a qualifying offer, so any trade proposal needs to be worth more than the value of a top 30-35 draft pick.  Matt Garza brought back an A- prospect, a B prospect and two C+ prospects, in a deal that favored the Cubs.  Lester won't bring back that much but an A-/B+ prospect and two B-/C+/C prospects isn't out of the question.

 

[EricFeczko]

I think we already lost a substantial portion of the savings we should have gained from a hometown discount. Starting the negotiations too low really backfired. At this point I'd make one last best effort to sign him to a 5 year deal. If that doesn't pan out, wait till the height of desperation at the trade deadline and see if you can trade him for something more valuable than the draft pick you'd get.

If the negotiations have stalled because the two sides aren't seeing eye-to-eye, then I'd agree. It's also possible that the negotiations have stalled because Lester doesn't want to negotiate during the season. In which case, I'd be careful about jumping the gun.
It's not a bad idea to gauge his value on the trade market anyways, as such information may inform how much the Sox should offer. I'm sure the Sox have been/are doing that, as they are with every player.
 

 

[amfox1]

Are you saying Garza was more valuable or the Rangers overpaid? Because I'm not seeing why Lester should fetch less than Garza did unless you're implying the latter.

 
The Rangers overpaid significantly.  They've even admitted it, sort of.
 
http://rangersblog.dallasnews.com/2014/03/jon-daniels-admits-concerns-about-garza-deal-with-chicago-cubs.html/
 

As Texas Rangers general manager Jon Daniels tries to plug injury-related holes on the opening day roster, he looks back with some regret on last year’s depth-sapping trade for Chicago Cubs right-hander Matt Garza.
“I thought way too short term with the Garza deal,” Daniels told the Arizona Republic. “That one’s got a chance to haunt us and haunt me.”
 

 

[Rasputin]

The real answer to this question is "When we're convinced we can't extend him" which requires a strong effort to extend him before the deadline.
 
We know they have talked. They must have a general idea of what would get it done. They now have an additional quarter of a season of excellent production to plug into the prognosticatron.
 
And if, perchance, he is traded, it should come with a very strong indication that they want to bring him back as a free agent.

 

[pdub]

If we trade Lester then we might as well trade Lackey and Koji for more pieces. Trading Lester puts us into rebuilding mode, something I can't see this team doing. Especially when I think we have a solid core that is a few moves away from being good. Trade for Stanton? Sign Scherzer? Sign Shields? Such moves can make us competitive again very fast. Plus, we definitely have the money to splurge wisely. 

 

[Rovin Romine]

If we trade Lester then we might as well trade Lackey and Koji for more pieces. Trading Lester puts us into rebuilding mode, something I can't see this team doing. Especially when I think we have a solid core that is a few moves away from being good. Trade for Stanton? Sign Scherzer? Sign Shields? Such moves can make us competitive again very fast. Plus, we definitely have the money to splurge wisely. 

 
You can't consider Lester as part of the core though.  He's a guy who plays for us in 2014 only.  The 2014 team looks deeply flawed at this point, with no guarantee that any of it's injured or underperforming players are going to turn the corner quickly enough to make a credible run at the post season. 
 
Think of Lester as a FA for 2015, which is what he is.  Then look at the 2015 team and ask yourself what we have.  Is the 2015 team strong enough to warrant Lester being one of the pieces that sucks up the remaining budget?  Or will we have what we seem to have right now - somewhat of a maybe-it-could-work-if-everyone-got-healthy/skilled core, but no credible way to make it competitive.  

 

[RedOctober3829]

 
You can't consider Lester as part of the core though.  He's a guy who plays for us in 2014 only.  The 2014 team looks deeply flawed at this point, with no guarantee that any of it's injured or underperforming players are going to turn the corner quickly enough to make a credible run at the post season. 
 
Think of Lester as a FA for 2015, which is what he is.  Then look at the 2015 team and ask yourself what we have.  Is the 2015 team strong enough to warrant Lester being one of the pieces that sucks up the remaining budget?  Or will we have what we seem to have right now - somewhat of a maybe-it-could-work-if-everyone-got-healthy/skilled core, but no credible way to make it competitive.  

My question to you is this: if you aren't spending on Lester, who are you adding to the rotation? Another FA or plugging in a kid? If you think the 2015 team can be competitive, then not keeping Lester or signing a big FA starter will keep this team from being good.

 

[Remagellan]

Obviously I'm biased, but I think we should regard Lester as the Cardinals did Wainwright--the veteran ace who will take pressure off the young guys as they acclimate themselves to the majors.  He's a proven performer in the playoffs, and whether or not you believe in such things, there is value in having a guy who's shown he can handle facing another team's ace in Game 1 of a playoff series.  

 

[amfox1]

If we trade Lester then we might as well trade Lackey and Koji for more pieces. Trading Lester puts us into rebuilding mode, something I can't see this team doing. Especially when I think we have a solid core that is a few moves away from being good. Trade for Stanton? Sign Scherzer? Sign Shields? Such moves can make us competitive again very fast. Plus, we definitely have the money to splurge wisely. 

 
Once the Red Sox are out of it, trading Koji, Breslow and Miller for prospects should be near the top of the list.  
 
2014 free agents (12) - Lester, Peavy, Uehara, Capuano, Badenhop, Miller, Breslow (team option), Sizemore, Pierzynski, Ross, Gomes, Drew (I would not consider Lackey a free agent since the option will obviously be picked up)

 

[amfox1]

Obviously I'm biased, but I think we should regard Lester as the Cardinals did Wainwright--the veteran ace who will take pressure off the young guys as they acclimate themselves to the majors.  He's a proven performer in the playoffs, and whether or not you believe in such things, there is value in having a guy who's shown he can handle facing another team's ace in Game 1 of a playoff series.  

 
True, but I think Lackey could also be that guy for 2015.

 

[Plympton91]

If the Red Sox don't think they can be competitive in 2015, then they have a significantly lower opinion of their AAA talent than most here and a significantly lower payroll in mind.

If they're not planning to be competitive in 2015, after having decided to punt 2014 by not bringing back at least Drew and Salty on Victorino/Napoli type contracts, because they had to make room for their "prospects" (say that word the way Allen Iverson says "practice") then they've failed the fan base.

 

[pdub]

Any chance of us being competitive next year means re-signing Lester AND adding a top-tier pitcher such as Scherzer. Doubront hasn't been efficient this season, Buchholz looks like he'll never reach his peak on this team. Lackey is solid but he's only getting older. Peavy is also struggling and is probably gone after this season. I can't see a championship rotation for 2015 having Lackey as the ace. He's a good pitcher and has balls of steel, he's just not a true ace.  

 

[mauf]

How often do players in a contract year who are good enough to fetch a comp pick get traded in the middle of the season? Going back a few years, you had Sabathia and Holliday, but those deals were under the old rules, where the acquiring team could end up with a comp pick. (Also, Sabathia was a lot more coveted then than Lester is now.) Going back further, you had a lot of deals, but I don't think you can draw instructive parallels from an era when clubs routinely ignored the value of comp picks, to say nothing of the lower value that GMs ascribed to prospects in those days.

The lack of useful parallels to evaluate what kind of package the Sox might get for Lester probably tells you all you need to know about the likelihood of such a deal happening.

 

[crystalline]

If the Red Sox don't think they can be competitive in 2015, then they have a significantly lower opinion of their AAA talent than most here and a significantly lower payroll in mind.

If they're not planning to be competitive in 2015, after having decided to punt 2014 by not bringing back at least Drew and Salty on Victorino/Napoli type contracts, because they had to make room for their "prospects" (say that word the way Allen Iverson says "practice") then they've failed the fan base.

Drew: "Prospects!!? We talking about prospects? I'm the best shortstop in the AL in 2013 and you talking about prospects?? Damn. PROSpects."



About the general idea of giving up on this season: It's not even June. Going 500 the rest of the way gets them to ~80 wins. 600 ball gets them to 86 wins. This team has a lot more talent than they've showed. I'm going to predict they end at 86 wins and have a decent shot at both division and wildcard down the stretch.

 

[Mighty Joe Young]

Drew: "Prospects!!? We talking about prospects? I'm the best shortstop in the AL in 2013 and you talking about prospects?? Damn. PROSpects."



About the general idea of giving up on this season: It's not even June. Going 500 the rest of the way gets them to ~80 wins. 600 ball gets them to 86 wins. This team has a lot more talent than they've showed. I'm going to predict they end at 86 wins and have a decent shot at both division and wildcard down the stretch.

 
Hmm .. no - going .500 the rest of the way gets them at around 76 and 86 
 
But is this team capable of playing at a .600 clip for the next 113 games - highly unlikely without some fairly substantial upgrades at , at least, 2 or three positions (C, LF/RF and possibly CF)

 

[Rovin Romine]

My question to you is this: if you aren't spending on Lester, who are you adding to the rotation? Another FA or plugging in a kid? If you think the 2015 team can be competitive, then not keeping Lester or signing a big FA starter will keep this team from being good.

 
It's a valid question.  My point was that you can't count on Lester as part of "the core."  Whether or not Lester is a good FA signing is another issue.  However, I don't think automatically signing Lester is a good idea.  (It may be a good idea, I'm just saying we don't quite yet know.) 
 
First off, "keeping Lester" looks like it's basically going to equal "signing a big FA starter."   If Lester wants "fair value" or is willing to take a discount, all that follows is moot.
 
Secondly, as you point out, part of the signing depends on whether or not the 2015 team will be competitive.   Here's the link to the Cots contracts page https://docs.google.com/spreadsheet/pub?key=0Ah4PW47PiAi-dGhxT2g1OG8zZXR3NVZPaUVBRHpzS3c&output=html
 
We have 78mil committed to:  
Postion players: Napoli, Ortiz, Pedroia, Victorino.   
SP: Lackey, Buchholz.
RP: Mujica, Breslow.
(Basically this sucks.  In 2015, there are a lot of question marks attached to this block of players - and it's almost half the budget.)
 
We control the following players subject to Arb (not part of the 78 mil):
Postion players: Carp, Herrera, Nava.  
SP: Doubront.
RP: De La Rosa.
(Again a ton of question marks - but at least we're not committed to contracts, and any 2015 expense would be tied to them showing legitimate worth this year.)
 
We control the following players, pre-arb:
Postion players: Bradley, Boegarts, Middlebrooks.  
SP: Workman.
RP: grabbag - Wilson?
(Again question marks - with the caveat that question marks are expected.)
 
So basically that gives us:
c: 0
1b: Napoli (Carp)
2b: Pedroia
ss: Boegarts
3b: Middlebrooks
lf: Nava
cf: Bradley
rf: Victorino
 
sp: Lackey, Buchholz, Doubront, Workman
 
rp: Mujica, Breslow, De La Rosa
 
***
I'm not sure how much the arb players will be worth, or if the team will renegotiate with Lackey for an extension.  However, looking at that lineup and that rotation raises legitimate questions as to just who will be productive in 2015 - or if they'll be competitive in the aggregate.  I can see them being competitive.  I can also see them completely sucking.  Either way, it looks like they'll have to take risks on players and/or hope that prospects can jump to the majors.  (Betts/pitching prospects.) 
 
I don't think it's a given that Lester is a "final piece" of the puzzle for 2015, and so an overpay probably isn't warranted on that basis.  In 2016, we have few commitments, but that just makes the issue trickier.  Pay market rate/top dollar for Lester now, or for someone else (preferably younger than Lester) this off-season or next off-season for the 2016 squad?  
 
The problem is that we have a lot of "potential," but it's hard to predict.  

 

[JakeRae]

I'm not voting, but my answer is trade deadline, if the team is still not in contention and they don't think they can work out a long term deal (or if he's willing to be a rental to a contender and come back to Boston after). Lester's age isn't really an issue as a starting pitcher. Position play contracts get ugly in the mid-30's quite regularly. Pitcher aging curves are far less predictable. Giving a 27 year old pitcher 6 years is not much less risky than giving a 31 year old pitcher 6 years. Giving the 27 year old 7 years is probably riskier. I would prefer Lester to stay in Boston long term and I think this team has enough talent to pull it together and challenge for the division this year. However, if the team continues to struggle and Lester wouldn't hold it against Boston if they shop him to a contender, trading him then re-signing him in the offseason would be the best possible scenario. We would then get prospects and get to keep Lester.

 

[ehaz]

I think this is one of those trades that only gets done if a desperate newly contender seriously overpays.  Like say,
 
COL: Lester, Uehara
BOS: Eddie Butler, David Dahl, etc.
 
Essentially, I'd be looking for a top 25 prospect that is reasonably close + a top 70 or two.  You definitely won't be getting Gregor Polanco for a half-season rental but I believe that someone a step below is a reasonable target.

 

[Just a bit outside]

I think this is one of those trades that only gets done if a desperate newly contender seriously overpays.  Like say,T
 
COL: Lester, Uehara
BOS: Eddie Butler, David Dahl, etc.
 
Essentially, I'd be looking for a top 25 prospect that is reasonably close + a top 70 or two.  You definitely won't be getting Gregor Polanco for a half-season rental but I believe that someone a step below is a reasonable target.

This has no chance of happening.  Rockies will not make this trade.

 

[ehaz]

This has no chance of happening.  Rockies will not make this trade.

 
You're probably right, but why trade Lester for anything less?  Chris Gentry isn't going to save the Red Sox in 2016, unless you're getting real talent then the exclusive negotiating window is probably worth more.

 

[Curll]

 

"On-pace" projections can be pretty funny the first few weeks of the season, but now we're over a third of the way in. Red Sox are on pace to finish 74-88. (With 17 walk-off losses! We're also on pace to go approximately 21-39 in one-run games.)
 
We'd have to go 63-40 the rest of the way to get to 90 wins. 54-49 to finish .500. 
 
Toronto is on pace to finish 97-65, 23 games ahead of us. Yankees are on pace to finish 81-81, 7 games ahead of us.
 
We would need to pass 8 teams in the standings to get the second wild card.
 
At least the Devil Rays suck more than us. They are behind the Astros now for the worst record in the league.

 

 

[MakMan44]

The only reason the Red Sox would trade Lester is if they're unlikely to sign him. Considering this that doesn't seem to be the case yet.

 

[Sampo Gida]

I find it hard to believe anyone is really giving up on the team this early.    I think they are one bat away which probably needs to be acquired via trade and parting with WMB and a prospect or two and one pitcher call up away from being able to go on a run.  I am positive Toronto will do another one of their patented summer fades and nobody else in the AL East is that scary.   In fact, one could argue the AL East is the weakest division in the AL if Toronto is just an illusion.   Good year to start off slow
 
For the long term, Lester is even more essential given the uncertainty of Buchholz and Doubront and the fact  Peavy and Lackey are likely gone by the end of 2015 (2014 in Peavy's case), not to mention the uncertainty of pitching prospects.   Certainly needs to be extended, but the price has probably gone up unless he does a mid season fade.

 

[BosRedSox5]

I don't know why you would consider trading him. The Red Sox are a big market team, which means they can flex a little financial muscle and extend guys they want to keep. Jon Lester is, by all reports, a great teammate. He's very consistent, he's a good guy to have around. Maybe he'll never win a Cy Young, but he's got big game experience, he's dynamite in the playoffs and he's the sort of guy you should feel comfortable making a long term financial commitment to. 

It'll probably get dismissed as scoutspeak, but isn't it worthwhile to have an experienced, dependable pitcher in the rotation that other young up and coming pitchers like de la Rosa, Webster, Barnes, Owens, Ranaudo and whoever else can look up to? Who can stabilize the rotation and start opening day during the life of his contract? 

Sure, I suppose you could say that trading Lester away helps open up a spot for those guys, but with Lackey moving on soon, and Doubront not really cutting the mustard it's hard to say the rotation will be too crowded in a year or two. 

 

[smastroyin]

I think the presumption for trading would be that since he is a FA anyway, you are only trading 2-3 months for him.  I suppose you could hope for something where you trade him for the rental stretch run then sign him back as a FA.  I wouldn't do it and it sounds pretty risky to me and not something you hear working very often.  The other thought is that they aren't going to want to bring him back as a FA anyway, so get something for him for the stretch run.  I don't think this is true, but it makes sense to trade him if it were.
 
I tend to think that trading Lester for prospects makes 2015 and 2016 into more "bridge" years.  Obviously there are other moves that could be made.

 

[Drek717]

Make one more hard push over the next few weeks to sign him.  If by the end of June they still can't come to an agreement then shop him around.  If the Sox are still struggling and a team is willing to give more value than a mid-30's pick + 2-3 more months of Lester then take the deal.
 
Lester can be a cornerstone pitcher but if they can't come to terms during the season it's an easy equation for the Sox FO.  At that point they'll be bidding against other clubs in the winter no matter what.  So if the trading team is willing to beat out the compensatory pick plus having Lester for a few months of a lost season then good for them and the FO sees where Lester's market lands in the winter.

 

[JimD]

Make one more hard push over the next few weeks to sign him.  If by the end of June they still can't come to an agreement then shop him around.  If the Sox are still struggling and a team is willing to give more value than a mid-30's pick + 2-3 more months of Lester then take the deal.

 
I think it was Alex Speier on WEEI who was recently speculating that the Sox have gotten buisness done in the past around the All-Star break, so we may see one more push with Lester's side around then.  If the sides are still far apart and the team is going nowhere, they'd have time to see what interest is out there for his services.

 

[FanSinceBoggs]

Would the Red Sox be better off (essentially) trading Jon Lester for Pablo Sandoval?  That is, the Red Sox would sign Sandoval after the season and lose a draft pick.  In turn, they would gain a draft pick when Lester signs with another team.  The addition of Sandoval, together with another year of development for Bogaerts, and the promotion of Betts to go along with the offensive core of Pedroia, Ortiz, and Napoli, would go a long way toward fixing the Red Sox's offensive woes in 2015. 
 
Is Sandoval a better long term investment than Lester?  Sandoval is two and 1/2 years younger than Lester.  While Lester is having a strong season, there is risk involved in signing a pitcher of his age to a long term deal, and there are so many examples of this.  While Sandoval has conditioning issues, he can play third base in 2015, and could move to 1B or DH later in his career.  I'm inclined to think that a long term contract for Lester involves greater risk than a long term contract for Sandoval.
 
But would the Red Sox have a good enough starting staff to win a championship in 2015 without resigning Lester or signing a guy like Scherzer?
 
Lackey
Doubront
Buchholz
De La Rosa
 
fighting for spots:
Webster
Barnes
Ranaudo
Wright
 
Would likely begin the 2015 season in the minors:
Owens
Johnson 
 
Even without Lester or Scherzer, the Red Sox would be loaded with starting pitching depth.  Of course, there is concern about the quality of that depth.  On the other hand, the Red Sox could resign Lester to a lucrative 20+ million dollar per year contract and he could respond by giving the Red Sox a 110+ ERA in 2015, which is good but hardly worth the kind of long term investment that Lester wants.

 

[bosockboy]

They could easily sign both though.

 

[FanSinceBoggs]

But then they would lose a high draft pick.  Would the Red Sox be willing to do that?  I'm not so sure.
 
However, signing both players and giving up the draft pick would make the Red Sox a much stronger team in 2015.
 
If the Red Sox finish with a protected pick, and that could happen, signing both players is a much easier decision.

 

[bosockboy]

Yes they will have to address the offense this winter, notably 3B/LF.