Cubs Have Reportedly Had Internal Discussions about Jon Lester and Justin Masterson

Theo Epstein and Jed Hoyer have said the front office will address the organization’s pitching needs and could add starters in the off-season if the situation, or situations, presents itself and benefit the Cubs moving forward.

The Cubs have very little financial commitments on the books for the big league team beyond this year and were able to roll over payroll from this season the front office earmarked to sign Masahiro Tanaka last off-season as well as the payroll saved by trading Jeff Samardzija and Jason Hammel to Oakland. The front office will have the financial flexibility to add veteran free agents to the big league roster as well as the prospect currency to trade for a starting pitcher if that is the route the front office thinks would benefit the Cubs in the long-term.

According to a report from the Sun-Times, the financial flexibility the Cubs will have “could mean a serious run at Red Sox free-agent ace Jon Lester or underperforming Indians ace Justin Masterson, players the Cubs have had significant internal discussions about.”

The Cubs being connected to Jon Lester and Justin Masterson was expected. The front office has a history with both starters from the years together in Boston. Theo Epstein, Jed Hoyer and Jason McLeod inherited Jon Lester while the trio selected Justin Masterson in the second round of the 2006 draft. Masterson was dealt to Cleveland, along with Bryan Price and Nick Hagadone, for Victor Martinez in July of 2009.

PrintThe Red Sox are at a turning point with Jon Lester. The 30-year old southpaw is poised to hit free agency at the end of the season after Boston and Lester have not been able to find a middle ground on an extension. Boston has five days to trade him or risk Lester walking away with only a draft pick coming back to the Sox.

Rob Bradford posted an excellent report Friday on where the Red Sox stand with Jon Lester.

While Jon Lester is putting up ace numbers and is in the conversation for an AL Cy Young award, Justin Masterson is not having a good year. Not only are his numbers bad but his velocity is down.

Jon Lester will start his new contract at 31-years old and Justin Masterson is a year younger than Lester. Long term contracts for starting pitchers are risky at best, but a risk the Cubs front office will likely take when they think the team is ready to start competing.

The Cubs were among several teams (Giants, Pirates, Braves, Orioles, Mariners and Nationals) that had top evaluators at Tropicana Field on Friday night to watch Jon Lester and David Price pitch according to Ken Rosenthal.

Jason Hammel

The Sun-Times spoke with Jason Hammel and the recently traded starter that made a lot of noise just before the deal with Oakland was announced did not shut the door on returning to the Cubs in the off-season.

Jason Hammel, like Scott Feldman, enjoyed his time with the Cubs. And like Feldman, who recommended Hammel sign with the Cubs, Hammel has put himself in line for a multi-year contract this off-season after spending four months with Chris Bosio and the Cubs.

Hammel told the Sun-Times he was hoping he had pitched well enough that the front office would not trade him. Hammel “found the sudden, jump-the-market trade tougher on him and his pregnant wife than he anticipated.”

Theo Epstein, Jed Hoyer and the front office took responsibility for the lack of communication with Hammel the day he was traded and smoothed things over with Hammel after the deal was done. According to the Sun-Times, “the Cubs tried to maintain good relations with Hammel.”

Jason Hammel mentioned to Gordon Wittenmyer that his time with the Cubs is “at the top of the list of the best baseball experiences” he’s had.

If Hammel knows he would be part of the Cubs plans moving forward, he told the Sun-Times the Cubs would be an option to sign with in the off-season.

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  • laredo

    Lester maybe. Otherwise it’s top, one – two starter material we need to seriously start competing. Price, Scherzer, etc. Hammel, Feldman, Masterson can be nice complimentary pieces but they best not be the focus of our free agent bucks. If and when trades look lucrative for our (hopefully) contention certain names need to be totally off that list. Right now I cannot think of even one major league player I would sacrifice Bryant to acquire. Not one. Nope, not even Stanton. Okay, Trout, but only him. I had to think about that one.

    • http://theboardridersuite.wordpress.com/ Theboardrider

      I don’t think Bryant is even on the table at all. No pitcher, outside of Kershaw or someone in his mid 20’s would make any sense. I’d splurge on Lester, Scherzer or Price but that’s it. I wouldn’t give huge money or a deal over 5 years to anyone else.

      I think it’s more likely we wait and see who becomes available in a trade. But I wouldn’t mind Hammel or Mastersom at the right price and length. Masterson would be a calculated risk.

      • J Daniel

        I would agree with you on Bryant. I think they will try to buy a couple of pitchers rather than trade for them at least at this point. If they could buy, for example, Lester and either Masteron or Hammel that puts the rotation in decent shape but will still need more. IMO it would be adding a #1 and a #3/4 on a really good team and would still need a #2 to be a serious playoff team.

        • http://theboardridersuite.wordpress.com/ Theboardrider

          I think Arietta can be our 2. Then slot Hendricks at 4, and to me, we are competitive next season.

          • J Daniel

            I agree in that they would be much more competitive for sure, especially if some of the young guys can hit while Rizzo, Castro, Castillo, and AA get better. Valbuana, Coughlan, … would be good role players off bench.

            I saw Hendricks pitch live Tuesday night and was very impressed! But I still would remain very conservative in my slotting with him. I would slot him at #5 at this point and if he proves better, which is possible, then that has the makings to be a fine staff. I still have the same approach with Arietta except I slot him at #4. So, at least in my estimation on building a playoff staff, they need a #1-3.

            This is where I think if they sign 2 guys, see how it goes with Arietta and Hendricks, a July deadline deal to add can be be made.

            It would still be my preference not to trade any of these young guys yet, unless they have the feeling (whoever they trade) is not going to make it and strike while value is high. For example, maybe trading Jackson and Vitters would have been beneficial and you could not get a bucket of balls for them now … just as with Barney. Bobby Hill in the Ramirez trade is a great example. It is critical to know your own talent.

          • http://theboardridersuite.wordpress.com/ Theboardrider

            You make some good points. And in a perfect situation I agree on the lower slotting. But I think it’s very conservative. Even if Arietta can’t quite consistently be the guy that throws no-hitters into the 7th inning, he would still probably be one of the best #4’s, if not the best in the league. It’s hard for me to imagine us going from where we are now to that luxury. I think that Arietta at 3 and Hendricks at 4 seems more likely. And, I may be the only one who feels this way, but I think that by 2017 or so, they could both be a slot higher, with Arietta even being a potential #1. I think that when he reaches Shark’s age, he will be a better pitcher than Shark is.

      • mutantbeast

        Board, I wouldnt even go beyond 5 yrs with Lester. 5/100 at the very best. Lester will be 36 at thge end of a 5yr contract and likely untradable. Scherzer has already turned down 8/144 with Destroyed. And I get a feeling the LAD is eventually gonna regret that Kershaw contract, as good as he is now.

        • http://theboardridersuite.wordpress.com/ Theboardrider

          Maybe something front loaded? Scherzer turning down that contract he did is just insane.

          I think there will likely have to be one of these type deals we have to make. Younger pitching isn’t available and we will need a guy like this, proven vet with rubber arm. Scherzer may be less risk due to mileage. Either guy can likely be effective past 35. Dominoes he’d but effective. At that point we should have internal guys ready and who knows what else?

      • Ross Scanio

        OK on Hammels. He and his wife must want to be in Chicago and be part of th Cubs wining the playoffs.

  • Tony_H

    Another view on Lester……”He’s a goner.”

    http://bostonherald.com/sports/red_sox_mlb/boston_red_sox/2014/07/nice_knowing_you_jon_lester

    Expect it to take not a 5 year $120M deal to sign, Lester, but a team going 6 years and closer to $140M. (Cubs could offer $20M signing bonus Years 1&2 $25M, Years 3&4 $20M, Years 5&6 $15M, which would pay him half of the money by the end of Year 2!!!)

    That’s a lot of money, but might be the cost to bring in TOR pitcher. The hard part if also factoring in that any 30 year old pitcher, isn’t likely to start 32 games for all 6 years.

    The Cubs though, can offer a big signing bonus to help reduce the later years salaries or just bring down a consistent annual salary. Whether it is this off-season or future off-seasons, this is going to have to happen and may need to happen twice. But the Cubs have a need to front load or use a large signing bonus, due to the offense going to be mostly filled by young guys who will be getting expensive when these contracts are going away. Signing a Lester or two, makes sense at this point. But after reading different articles and having all of us watch first hand the Garza, Demspter, and now Samardzjia comments, once has to wonder if Lester does want to move on and that is why he hasn’t signed a contract with the Red Sox. Maybe he has bigger plans for his next 5-6 years!

    • dwalker

      Said it in another article but say it here aswell. This might be the last year of bottom feeding and the last time the cubs have a protected first round pick. The window is starting to open and they won’t want to waste this one.

      • Tony_H

        That is true and is why it might make sense to go after 2 arms this year, versus spreading it out over 2 years.

        • Denver Mike

          I suggested it right after the Russell trade, but Baez+ for Price, and Lester as a FA would be a mighty fine TOR!

    • http://theboardridersuite.wordpress.com/ Theboardrider

      I think its do it. 6 years is the price to pay.

  • mutantbeast

    Lester, yes. Please, stay away from Masterson. Even when healthy(which he isnt right now), he cant retire lefties. Hes as frustrating to Indians fans as Carlos Zambrano was to Cubs fans. James Shilelds would be a better option 1A than Masterson.

    • Tony_H

      I agree on Shields as he won’t take as long of a contract.

  • Richard Hood

    I hope at this time they are starting to have internal questions about Lester, Masterson, Price and anyone else they can get their grubby little fingers on. They need options for the top of the staff at this point and buying them in FA is going to be easier than trading for them or developing them.

    • http://theboardridersuite.wordpress.com/ Theboardrider

      I think there absolutely is. And most likely Lester. Theo knows and respects him and vice versa. But really, 2 of them wouldn’t shock me.

    • J Daniel

      They have discussions every day on how they are going to get better.

      • Richard Hood

        I Agree I just was meaning that they do not need to just look at Masterson and Lester but what can make the pitching better at what value.

        • J Daniel

          No doubt. I think they have these discussions/thoughts on every position every day.

  • Jeffrey Rogers

    If you want to get a TOR pitcher under the age of 30, most likely you will have to trade for him. Scherzer turns 30 in a couple of day, Lester 30+, Price turns 29 next month.

    Baez and another player brings back a younger arm.

    Cubs are probably a year away from risking a long term deal on a 30+ year old pitcher.

    • Roll

      Agree on the trade aspect for a TOR pitcher, If the Cubs do go after Lester in Free Agency they will have to out bid the likes of the Yankee’s Angeles, Rangers, Mariners so it is going to take north of 5 years and in the $140-150 million range. In addition, with the Cubs arguably still 3-4 years away from a serious playoff run, if a contending team does offer the same type of money the Cubs to a Lester type FA he will more than likely sign with a contender.

      • http://theboardridersuite.wordpress.com/ Theboardrider

        I think Lester sees us as closer than that. 2016 ready. And he loves Theo and likes idea of winning with Cubs. I can see us getting it done for he and Price.

        • cubtex

          Can you post that link where Lester says he loves Theo?

          • http://theboardridersuite.wordpress.com/ Theboardrider

            Did you ever grab Tito’s book? The quote was actually “lots of respect and admiration.” But in pro sports terms that’s like saying love.

          • cubtex

            You can respect and admire your boss but that doesn’t mean you love the guy

          • http://theboardridersuite.wordpress.com/ Theboardrider

            Man ST, why you always gotta be so dang literal! But fine, I can’t argue with you.

          • cubtex

            Bite your tongue! That word has never been linked to ST :)

          • http://theboardridersuite.wordpress.com/ Theboardrider

            LOLOLOL! I’m gonna get some serious mileage out of ST. At this point, I already can’t even recall a time when I called you anything else. :)))))

          • John_CC

            I think he means “sexy texy” as you dubbed yourself yesterday.

          • http://theboardridersuite.wordpress.com/ Theboardrider

            Yessir!

          • cubtex

            I knew that. Meant the word liberal has never been linked to myself. That was the worst thing Rider has ever said to me

          • Tony_H

            I think the word was literal which isn’t the same thing as the awful name calling you thought it was :)

          • cubtex

            Have a great weekend bud! Off and running

        • Jeffrey Rogers

          WOW, that is a lot of cash and risk for two guys already in their prime years.

          I can see one of those and may be a 2nd tier guy, but not both. It will probably be $250,000,000- $300,000,000 to get both Lester and Price.

        • Roll

          I also don’t see Ricketts/Theo agreeing on a $140-150 million dollar contract this year when he has not shown he is willing that type of money on payroll yet. From the business side “if” Ricketts does start construction on Wrigley this year that will consume a large amount of cash and with very little new revenue coming in I don’t see payroll increasing much past $70-80 million in 2015 at which point they will not have one pitcher consume 1/3 of total payroll next year, maybe in 2016-2017. Hell they wouldn’t even offer Jeff $100 million contract that would have started in 2016.

      • Tony_H

        3-4 years??? 3-4 years we will be wondering how to play all of these great players, due to winning the World Series and young studs like Jimenez and Torres needing to play everyday, not just be roll players to win the World Series.

  • JasonOfTheBurbs

    My opinion: Masterson is not an Ace. I have had this guy all year in Fantasy CCO, and he put up more negatives than any pitcher I have seen. When you look at his previous numbers, there is nothing amazing either. He is basically a poor man’s Jeff Samardzija, with worse numbers, same age (so not a puppy anymore) and is extremely overrated. He is basically an Edwin Jackson…run away…run away very very briskly.

    • Tony_H

      Never been a fan of Masterson, but if he falls far enough to need to do a 1 year deal to build his value back up, I would be fine with that. He seems very similar to past 1 year deal guys at the moment, but obviously having had better success in previous years.

  • BigJonLilJon

    I wonder about either. Lester is a stud, but the age of either concern me. I like the idea of front loading a contract for him and due to his history with Theo, I think Theo could sell him on the future here. You can have Masterson.. I don’t want him.
    I don’t see the Cubs signing 2 “major” FA SP’s this off season. I see 1 being signed and a plan B 2nd tier guy. Shields? Possibly another TOR after the 2015 season. I could see Hammel coming back, although he hasn’t fared to well in Oakland.
    I also hope we don’t do a trade of the young prospects. I may be able to be talked into Baez because my gut tells me he wont make it. Wont learn to control the strike zone. Though I do think he could turn into a “Soriano Light”. A streaky guy who hits in waves and has waves of cold spells. I think the chances of Bryant going any where is less than 0%!
    Arrieta can be a 2 or 3. Straily – I think will get it turned around similar to what Arrieta did to become a 3 or 4. Hendricks, Wood, et all to fight it out to finish the rotation. Most of the better SP’s we have in minors are in the lower levels of the minors for us right now I believe, and this could get us where we need to go while waiting for them to develop fully.

    • http://theboardridersuite.wordpress.com/ Theboardrider

      I agree with you. If we can sign two, do it. I prefer Lester/Price, I don’t think Scherzer seems reasonable. If not Lester and Price, then one plus Sheilds.

      But if we go into next season with:

      Lester/Price
      Arietta
      Hendricks
      Wood
      EJax/Wada/Beeler

      It’s not a WS winner but we’d win a lot of games if our offense is a bit improved.

      I’d prefer:

      Lester

      • http://theboardridersuite.wordpress.com/ Theboardrider

        Sorry, iPad wouldn’t let me finish for whatever reason…

        I’d prefer:

        Price
        Lester
        Arietta
        Hendricks
        Wood

        or

        Lester
        Shields
        Arietta
        Hendricks
        Wood

        I think if we only sign one and have Arietta at 2, then we could make a deal midseason, or next offseason. But even, standing pat, in 2016 we could see:

        • http://theboardridersuite.wordpress.com/ Theboardrider

          Worst case in 2016:

          Lester/Price
          Arietta
          Hendricks
          Edwards
          Black or Stinnett/Blackburn/Johnson/Black

          2017:

          Lester/Price
          Edwards
          Arietta
          Hendricks
          Black/Tseng/Stinnett/Blackburn/Johnson/Cease/Steele/Sands

          AT that point obviously the options start to become too numerous to really get into.

          • http://theboardridersuite.wordpress.com/ Theboardrider

            I do think in 2016 and 2017, depending on standings, we could absolutely pick up a deadline guy for playoff push. But by 2017, we will have several internal guys that will be getting to 3rd and 4th year in system and I think we’ll be fine.

            I don’t want to trade any bats until we have to unless someone makes us an offer we can’t refuse for a young TOR type. But even then, I’d rather probably wait. I like the strategy of stacking bats. Let’s make sure we have an effective 1-8 in batting order before we decide who to unload.

        • BigJonLilJon

          Option 2 is what I am liking. If the young bats can play from April on, I think that could be a playoff team. Can be buyers at deadline for a SP if needed also.

      • http://theboardridersuite.wordpress.com/ Theboardrider

        Dang it, my iPad isn’t letting me edit even in a comment I’m already in! The bar with “Follow,” and “Share,” locks in place and I can’t read what I’m writing. So I click off and try to get it away and then it won’t let me back into my comment!

        I meant to say Scherzer seems unreasonable, not reasonable. I understand his take and by all means, get what you can. But at 30 to turn down 7 years 144 million!? Whatever he is after is going to be too rich for my blood. Let the Dodgers or Yankees pay it. I don’t want to be saddled with those dollars unless it’s 80/20 front loaded and we can release him after 5 years or so.

      • J Daniel

        Would ABSOLUTELY LOVE Lester and Shields! Now you are starting to talk about a playoff staff. EJax will be gone, somehow, IMO. Even if it saves $6 million to be used on someone else, it probably needs to be done. The other alternative is to slot him as your #5 but he would be an expensive #5.

        Not sure I agree with you on Wood unless he is slotted as a #5 as well.

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