Updated: by

jon lesterRarely does an elite starting pitcher change zip codes in the week leading up to the trade deadline, especially one that was part of a world championship team the year before. However the Boston Red Sox find themselves in a difficult situation with their ace Jon Lester who is set for a major payday as a free agent this winter. There’s mutual interest in keeping the southpaw in Beantown, but the two sides weren’t able to agree to an extension in Spring Training and a deal before the end of the season seems unlikely at this point. The 48-57 Red Sox have already dealt one of their starters, Jake Peavy, and should take advantage of a market inefficiency and deal Lester before July 31st as well.

Lester, 30, is in the midst of an outstanding season in which he’s posted a 2.52 ERA and a 2.63 FIP in 143 innings pitched. His 4.5 fWAR on the season has already eclipsed last year’s mark of 4.2. The Red Sox second-round pick in the 2002 amateur draft is owed around $4 million for the remainder of the season and is all but guaranteed to receive a qualifying offer should he remain with the organization beyond the deadline. There’s no question that Lester would be a significant addition to any team looking for starting pitching help, and there are plenty, and could easily be the best available starter given the uncertainty surrounding David Price.

The Tampa Bay Rays have been on a hot streak of late and have propelled themselves within a few games of a wild card spot and may prefer to hold on to their ace for the stretch run. Reports indicate that they need to be blown away by an offer for their star and have yet to be. The major point of contention for the Rays, no doubt, is Price’s salary is expected to be in the $20 million range for the 2015 season, his last year of club control before hitting free agency. The Rays are built to win now however, and at this point in time he seems more likely to be dealt in the offseason. Although plenty could change before Thursday’s deadline.

[pullquote]Lester owns a 110-63 record in 241 starts across nine big league seasons. His 33.7 career fWAR is 15th among active pitchers and is ahead of both Cole Hamels and Clayton Kershaw.[/pullquote]

We do know that Tampa Bay is looking for a blue chip prospect, see the Seattle Mariners Taijuan Walker, as well as a couple other pieces in exchange for Price considering the acquiring team would have an extra year of control. Lester would be a pure rental should he be dealt this week and the acquiring team wouldn’t be able to cash in a draft pick if he signed elsewhere as he’d be ineligible to receive a qualifying offer at season’s end. So what would two months of Lester cost? A lot.

Perhaps the best comparison for a Lester deal would be the July 2012 trade that sent Zack Greinke from the Milwaukee Brewers to the Los Angeles Angels. In exchange for two months of Greinke the Brewers received Jean Segura, Johnny Hellweg, and Ariel Pena. Segura was ranked No. 55 on Baseball America’s Top 100 Prospects list entering the 2012 season and is having a down 2014 after a 3.3 fWAR 2013 campaign for the Brew Crew. Hellweg and Pena are both playing at Triple-A this year and only Hellweg has reached the major league level where he played a handful of games last year.

Greinke had a 3.44 ERA and a 2.53 FIP in 123 innings pitched for the Brewers at the time of the trade so one could argue that two months and a potential playoff run from Lester should net more than what the Angels sent for the right-hander. There’s been a rumor circulating today in which the Red Sox have discussed sending Lester to the Los Angeles Dodgers in a deal involving outfielder Matt Kemp, but several outlets have cooled those reports and nothing appears to be imminent between the two clubs at the moment.

The Dodgers could be a fit for Lester as they’ve also been connected to Price and the idea of sending Clayton Kershaw, Greinke, Lester, and Hyun-jin Ryu out in a playoff series has to be awfully tantalizing. Los Angeles is loath to trade top prospects Joc Pederson and Corey Seager in a trade for Price but may be willing to move one of them in the right deal. One could argue that sending Pederson to Boston in a one-for-one trade for Lester would be an overpayment let alone adding another piece or two to the pie.

The Giants probably wouldn’t be interested in Lester now that they’ve added Peavy, but the New York Yankees, Toronto Blue Jays, St. Louis Cardinals, and Mariners have had varying levels of interest in adding a top tier starting pitcher according to reports, but it’s unlikely the Red Sox would trade Lester within their own division, even if he is willing to re-sign in Boston despite being dealt.

ESPN’s Buster Olney also tweeted today that the Red Sox are still listening on Lester and would be willing to trade him if their asking price is met, and it could be higher than the draft pick they’d receive if he walked. Well that much was obvious — why would the Sox deal for something less than the first-round pick which would likely be in the No. 30-40 overall range? Stranger things have happened of course, but it’d likely take multiple pieces to land the left-hander.

Seager, the younger brother of Mariner Kyle Seager, entered the year as the No. 37 prospect in baseball according to Baseball America, so a package including him and a couple Double-A types of players that offer some upside would be similar to what the Brewers received for Greinke while accounting for the fact Lester likely has slightly more value. It’s worth noting he’s playoff proven and has had no issue with pitching in the spotlight.

The Cardinals have plenty of prospect currency to deal from but it’s doubtful they’d want to give up an Oscar Taveras or a Carlos Martinez in exchange for two months of Lester. There’s a possibility they’d deal Tavares and another fairly significant piece in exchange for a year and a half of Price, but even that appears slim.

The defending World Series champions have had a disappointing year riddled with injuries and under-performing prospects and have already started turning their attention to 2015. If they feel their best shot at extending Lester is to hold on to him until the offseason, that’s a chance they’re willing to take. Though considering the southpaw is thought to be looking for a six-year deal in the $140 million range, a la Cole Hamels, and the Sox are said to have offered four years and $70 million in Spring Training, it could be difficult to consummate a deal regardless.

Bottom line: with David Price looking more and more like he’ll stay with the Rays for the time being, Lester would easily be the best available starter on the market and Boston should have no problem picking up at least one elite prospect if not a pair of very good young players in a trade. Or even Kemp or another major league player if those talks end up materializing.

The draft pick would be nice, but the Red Sox are in a position to turn the ship around quick and be serious contenders in 2015. They have plenty of young talent and a solid pool of pitching depth to work with and adding to it would only be a good thing. Considering the potential return Lester could net, Boston should take the risk and deal their ace before the deadline on Thursday. It doesn’t sound as though extending him will be any easier come November and December, and they simply can’t let a player of Lester’s calibre to walk for a draft pick.

Just ask the Yankees about losing Robinson Cano.

Latest posts by Tyler Carmont (see all)


  1. Avatar

    You are right rjfrick. I will take that one. When I posted that it was really late last night and almost immediately I wanted to take it out. I did though say that could be his “potential peak” comp and that he will most likely never reach it. I was merely comparing tools at present to what we know Henderson was. Speedy leadoff hitter with surprising pop and played a corner outfield spot. I definitely dont expect ricky numbers or anything really close but tools is all I was comparing. Other than that I do feel that was a really crappy example and could use another as an example but Im drawing blanks at the moment.

    As far as the comparisons Jerry was referring to what I said but he didnt read what I said right. I never compared them as far as the player Castillo could be, I was stating that because of Cespedes and Puig success Castillo will be the next big cuban and be paid like it. I went on to say he is not even close to their skills and isnt worth it money wise to their skills. Granted both players are not making much money to the their production but to pay him the same you are going to get less production to relative cost. I hope that makes sense.

  2. Avatar

    And nighthawk, no offense but you are comparing Castillo to one of the greatest 50 players to ever play. Come on man. Let’s all calm down here. Castillo is more Jorge Soler then Ricky Henderson.

  3. Avatar


    I don’t know what the heck you are taking about man. Seriously. The first two paragraphs of your post were indecipherable. I never comped Castillo to anyone. You made a definitive statement about Castillo being up for September if a team (the Ms) signed him immediately. You are wrong, flat, dead out wrong on that. Your right Castillo isn’t Cespedes, Abreu or Puig. All were better players and were viewed as better players then Castillo. I’m not just stating dribble, make thoughts come from industry professionals not the internet or Baseball America.

    And I’m sorry you were misinformed if you thought Abreu’s bat was slow. Anyone who watched the guy could see he could rake, but media people need something to write about and what you were reading was blatant nitpicking. Could he not get around on a 96 mph fastball on the inner half? Yep. Every MLB player in the history of baseball has had trouble catching up to that pitch. But players adjust and if tries it too many times or gives a tell away that ball will end up in the seats.

    Bottom line is you can wish all you want but Castillo isn’t seeing any MLB action this year. None.

  4. Avatar

    I wasnt saying that the M’s shouldnt sign him. I would like them too definitely. The thing to take into account is that we are not the only team wanting him so it may take more to get him. As for the conditioning thing it really doesnt matter how much muscle you have conditioning is more about endurance than muscle (even though muscle is big in and of itself) and apparently multiple scouts from multiple teams not just 1 or 2 came away with this thought. I have seen his video’s and clips and you are right he could be a major upgrade but he could also be a complete flop. Im glad that the M’s are having him come on here for a private workout on Sunday. It not only shows they are impressed but it shows that they are willing to go the extra mile for the possibility of signing him. I will say this I will listen too and believe in what most scouts say simply for the fact that they are paid for the evaluations and have much more training and experience then anyone of us bloggers on this subject.

    While I believe that Castillo can and will become a solid regular I want him to be paid like solid regular. The problem with the M’s right now is their self imposed budget that according to the new team president is “well over 100 mil. and he cant stand hearing the 89-90 mil rumor thats out there”. Yes they have commited to spend 24+ mil on Cano and Felix but the rest of the team is making pennys. Think about that, half of your 25 man roster is paid to 2 players the other 23 make up 40-45ish mil. Those “cheap” players wont be that way for long and we really dont have any long term commitments other than those two anyway. They have plenty of money coming in we all know this but the way they have worked and continue to work we cant expect them to open up their wallet to the extremes with these multiple 10-15mil performers that will be coming shortly (Seager, possible Iwakuma extention, any possible of coming via trade, etc.).

    I was only Cespedes and Puig as examples in the sense of production and there relative costs. You are completely right that you cant compare them because they are different types of players but at the same time the only tool that Castillo offers to compare to their level of tools is his speed. They out perform him on pretty much everything else. His cost should reflect that in a sense that he is not worth what they are but he will get paid like it because of them. I hope that makes sense. He is the new cuban player on the block and people will drool. I personally want to keep a level head on this guy. He is a speedy leadoff type hitter with some pop and he should be paid like it. The amount he gets paid is the only concern I have. Actually now that I think about it and I might be going out on a limb here but I think a “okay” comp to him would be Ricky Henderson. A strong corner OF with some speed, and pop and a chance to develop further. That is a stretch but that is a great player if he reaches Ricky levels but I dont expect that. Like I said big limb there but I do want the M’s to snag him just hope it doesnt bite us one way or the other.

  5. Avatar

    Nighthawk and rjfrik,

    I don’t mean to sound cheeky, but neither Cespedes nor Puig were seen as Cespedes or Puig type talents before they came over. From reading the scouting reports and seeing video of him, I don’t those guys are good comps at all. Different types of players. Castillo is more of a speed player. More importantly, there is a huge gap between what those guys are and a solid upgrade for the M’s. A player doesn’t need to live up to those lofty standards to really help the Ms.

    At the most general level, I think a lot of comps based on nationality are just lazy. It would be like saying “he’s no Mike Trout” for any player from the East Coast. He’s not the same type of player as any of those guys.

    Regarding your comments about conditioning, I’m sorry but that’s just ridiculous. Have you seen the videos of his workout? He’s absolutely ripped. That’s the first thing you notice about him: he’s a physical freak. He is also an easy 70 runner. All scouts agree about that. If he’s got conditioning problems, I’d like to see what ‘good shape’ looks like. He’s a physical specimen who is insanely fast.

    He’s not comparable to Puig at all, as Puig was 21 when he signed and was in the majors the next year. Cespedes and Abreu had much longer and more distinguished track records, but were mainly power hitters. Castillo isn’t really like either. He’s a speed/leadoff/cf player who has good power, but he’s not a monster like those guys. The only reason why those comps matter is because it shows that very good players from Cuba have a tendency to be very good players in MLB. Castillo was good in Cuba, and he’s got very good tools. He’s a good bet to have success in MLB sooner than later.

    Even if he just ends up a solid regular, he’d be worth Puig money (oddly,every but the Dodgers thought that Puig himself didn’t deserve that contract at the time). He migh bust. But he could also be the next star out of Cuba. Teams have to take risks sometimes.

    Everyone should take the ‘scouts said x, off the record” comments with a grain of salt. There is lots of misinformation out there. Remember how slow Abreu’s bat was, and how he would be able to hit ML pitching? There is a reason why almost every team in baseball went to Castillo’s workout the other day, and why lots of clubs have private workouts: he’s a really good prospect who might be able to transition straight to the big leagues. The Ms need to be in on guys like this.

  6. Avatar

    Castillo won’t be up in September even if they signed him today. He would be lucky to get on a minor league roster if signed. If the M’s do sign him he will head off to the Arizona fall league and depending on how he does there he either will have a shot to break camp with the big club next year. This isn’t Abreu or Cespedes. Even Puig spent time in the minors.

  7. Avatar


    While I too would like him on the M’s squad there is a big thing most are overlooking here. Castillo is not Puig or Cespedes type talent. He is a solid player but lacks that “star” upside big time. The real problem with him is because of the recent success of the cuban players and he is really the only one worth his salt at the moment he will get paid like puig. I do not want the M’s to hinder the “limited” budget currently and in the future on a player that isnt worth what he is.

    Jason had scouts tell him that they were concerned with his conditioning at his major showcase last week. He was getting ready for this big showcase and was not in the best shape he could of been? To me that doesnt pass the smell test. Could he be a solid player with a Puig type attitude? Puig’s attitude is questionable (much better recently) but he has played at such a high level that you can sort of overlook the immature attitude.

    Lastly I do find him very intriguing, very fast speedy guy with surprising power. He played CF but his arm is average for a left fielder from what I have read. He could be a very good 1, 2 or bottom of the order hitter. That would be a huge upgrade to our OF and we could use the help for sure but I wouldnt just throw Puig money (as little as it is really) at him just because he is the newest cuban of note off the boat. Again though having said all this I would like him but there is a line at the moment so we will see how it goes soon.

  8. Avatar

    Rusney Castillo makes way too much sense.

    Do it, Jack!!!

  9. Avatar

    Seattle is a MUCH BETTER team on the road, so it was somewhat predictable that they would have a lousy run here after the allstar beak. Then you lose Saunders and a thin outfield gets real scary. I still have hope that we can stay in and maybe even get that 2nd wildcard even if we can’t make a major move.

    It sounds like Jack Z is exploring every option and still has money to work with. As long as he doesn’t do something desperate (give up Walker and Franklin for a rental player like Lester) then I will be ok. Like Jerry I am nervous, but the deadline will come soon enough.

    Don’t lose hope Mariner fans!!! Either way we are competitive/relevant and that was all any of us could have realistically hoped for when the season started.

  10. Avatar

    Sorry for the novel. Can’t help it. I love the trade deadline, and its been ages since we’ve been relevant or interesting this time of year.

    “All Seattle needs is a good offense, with their pitching. A decent hitting RH outfielder and a firstbaseman would go a long way.”
    Unfortunately, that’s a lot easier said than done. I hope they can do something, but there just aren’t a lot of those types of guys available.

    I think rjfrik is still mad about DJ Petersons status as an elite prospect.
    By the way: MLB.com just updated their top 100 list. Peterson was 55. Good, but not elite.

  11. Avatar

    LOL. Standard procedure around here adrich1. Over the years we’ve had a few Jerry’s come and go. Can’t remember the name of the last guy. Maybe Edman remembers?

  12. Avatar

    They’re still in it. If people here think that it’s going to be 2 runs or less for the rest of the season, then halfe fun with it. All Seattle needs is a good offense, with their pitching.

    A decent hitting RH outfielder and a firstbaseman would go a long way.

  13. Avatar

    Jerry wrote more words than Tyler. Yeesh.

  14. Avatar

    Just to elaborate a bit on the comments above: I think this team has been good, and seems to be heading in the right direction.

    The nice things we’ve seen in the first half:

    -Lloyd McClendon is the shit. Love the guy.
    -Felix is in the drivers seat headed towards the Cy Young
    -Iwakuma showed that last year wasn’t a mirage.
    -Chris Young and Roenis Elias came out of nowhere and helped contribute to one of the best pitching staffs in baseball
    -the bullpen has been lights out, and almost everyone is cheap and locked up for the next few years.
    -Paxton has good when healthy, and should be back soon.
    -Walker is getting his first prolonged taste of the big leagues.
    -Robinson Cano earned his ludicrous paycheck.
    -Mike Zunino is so good defensively that any offense we get from him is gravy, but I think he’s a good bet to have a breakout either in the second half or next year.
    -Kyle Seager to another step forward, and is now a legitimate All-Star caliber player
    -Michael Saunders looked good this year

    Even if the M’s do fall back and fail to make the playoffs, this season has been a success.

    I’m just beginning to temper my expectations a bit.

  15. Avatar

    Anyone get the feeling that the M’s fortunes have changed, and not for the better?

    I hate to be a pessimist, but this team always seemed to me to be winning on smoke and mirrors, and their 3-7 record since the ASB seems particularly ominous. Every team has a slump every now and then, but the Blue Jays and Yankees have already slipped past us in the WC standings, and KC is only a half game back. I’ve got a bad feeling.

    The pitching has propped up this team, but the last few weeks have shown that its really hard to win if you don’t score runs. In those 10 games, we’ve scored 21 runs. Thats not good. And four of those ten games went to extra innings! In the early part of the year, it seemed like we benefited from pitching and an unsustainable number of HRs. Now, the HRs have stopped.

    You can’t win that many games when your team is dead last in OBP and SLG.

    So I’m left wondering what is more likely to happen: 1) the M’s end this little slump, and get back to winning the way they did early this year, or 2) the team’s surprisingly good results get way less surprising, and they revert back to a ~.500 team. I hate to say this, but I think the latter is closer to their true talent level.

    Ackley is starting to heat up, as he’s done a few times late in the season in the past. Smoak, Morrison, and Hart look done. Jones is looking more and more like an early season anomoly. Zunino is good, but he was rushed through the minors and isn’t ready to be a core of the offense yet. Morales is solid, not great when he’s good (like in 2013), but hasn’t been that guy yet. Right now, we have two good players – Cano and Seager – along with a third on the DL in Saunders. I know that this might sound like me just being a Negative Nancy, but I have a hard time seeing how this team will get turned around. Even if they add a good player, I still think this team is more than one reasonable upgrade away from being a legit contender.

    Any improvement is certainly not going to come from the pitching. Even during this downturn, they’ve pitched really well. Expecting an improvement is unrealistic. Simply maintaining the status quo is already a tall order.

    The more I think about it, the more I think the M’s should limit themselves to modest, low cost moves (Morales being a good example) or players who can help in the long term. Guys like David Price don’t make much sense to me at all.

    Hope I’m wrong about the fortunes of this team. But I’ve got a bad feeling.

Leave a Reply

Your email address will not be published.

This site uses Akismet to reduce spam. Learn how your comment data is processed.