Jon Lester Reportedly an Off-Season Target and Max Scherzer is on Cubs Radar

When the Cubs claimed Cole Hamels off waivers last week, the baseball world took that as a good indication the Cubs have the finances to add a top of the rotation starter this off-season and will be a player in the free agent pitching market. And according to a report from Patrick Mooney, the Cubs are prepared to make a nine-figure investment in a frontline pitcher that could start game one of a playoff series at Wrigley Field.

With the position playing prospects pushing their way to the big league club, the front office is expected to focus on adding pitching to the team and to the organization over the next 12-24 months. But there are a couple of top of the rotation starters that will hit free agency at the end of this season that many expect the Cubs to try to sign to lead the rotation going forward.

Jon Lester

The Cubs are expected to target Jon Lester this winter. And according to a report from Ken Rosenthal, “Some of Lester’s former teammates already project that he will end up with the Cubs, reuniting with Theo Epstein and Jed Hoyer. The Cubs, by claiming Hamels, showed that they have the money to make such a move happen.”

PrintThe Sun-Times reported last month the front office has already had internal discussions about Lester and Justin Masterson and Nick Cafardo reported “the Cubs are ready to spend for pitching.”

Lester would not cost the Cubs a draft pick, or the assigned slot money for the second round pick, and the front office “would rather sign free agents than trade away their best prospects” according to Cafardo.

Jon Lester has not hurt his stock since the trade with Oakland. Lester is 2-0 in two starts with a 1.72 ERA and a 0.96 WHIP (12 hits, three walks, 11 strikeouts, 15 2/3 innings) with the A’s and signing the 30-year old southpaw will not be cheap.

Cole Hamels

The Cubs interest in Cole Hamels could continue in the off-season. Nick Cafardo reported Sunday that the Cubs, along with the Rangers, Red Sox, Dodgers and Angels, are seen as “major players” for Hamels in the off-season.

The Cubs and Phillies could not agree on a package of prospects for Hamels before the negotiating window closed and by the front office claiming Hamels it kept Ruben Amaro from possibly dealing him to another team and taking away a chance of trading for him in the off-season.

Due to the amount owed to Cole Hamels (four years and $96 million) plus the cost to acquire him, the Cubs will likely focus on a starter that would only cost them a long-term contract and the risk associated with signing any pitcher to a big contract.

Max Scherzer

According to Nick Cafardo, Max Scherzer will be on the Cubs radar this winter. Scherzer hits the open market this winter after turning down big money from the Tigers last off-season, six years and $144 million. Scherzer’s numbers are still good, but not to the level of his Cy Young season of a year ago, and Scott Boras is his agent, so it will cost the Cubs more to sign Scherzer than the contract he rejected from the Tigers. Plus, Detroit will make Scherzer a qualifying offer and attach draft pick compensation to him.

Justin Masterson

The Cubs current front office drafted Justin Masterson when they were calling the shots in Boston. And according to a report from the Sun-Times last month, the Cubs have had internal discussions about the former Indians starter that was traded to the Cardinals.

Masterson is obviously not at the level of Jon Lester, Max Scherzer or Cole Hamels, but if he’s healthy his numbers figure to improve in the National League, despite the way he’s pitched in two games for St. Louis since the trade.

Like Jon Lester, Masterson is believed to be high on the Cubs list of starting pitchers that will be available this winter, but he’s not the top of the rotation starter many feel the front office will try to sign, or trade for, in the off-season.

Other Pitching Rumors

The front office is already working on the off-season and the team has scouts making sure their reports are up to date on players in their areas. The Cubs must be as prepared as possible in case one of the other 29 teams call and making sure the reports are current before the minor league season wraps at the end of the month is key for the winter. According to a report by Jeff Joyce (The Front Office, MLB Network Radio) passing on information from Andy Martino of the NY Daily News, the Cubs sent two scouts for Noah Syndergaard’s start last Thursday and the Cubs have been paying extra special attention to the Mets’ Triple-A team, the Las Vegas 51s, where Noah Syndergaard is currently pitching.

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  • Chris K.

    Woohoo!

  • SirGladiator

    It seems that St Louis did the Cubs a big favor, signing Masterson and showing what would happen if he got his change of scenery and a switch to the NL. He’s still just as terrible as ever, worse even. So unless he turns things around between now and the end of the season, there’s no reason to even consider him for next year, unless we’re just looking for a guy who could actually make Jackson look good by comparison, in which case we’ve definitely found a prime target :) . Lester is the guy we want, he wants to be here, we’ll sign him in the off season. I don’t think the odds are great on Scherzer, as he seems to want more money than he’s worth, but never say never. Right now adding Lester to our rotation and subtracting EJax from it, that alone would make such a huge difference. Thanks to our huge financial flexibility and the fact that bigtime Superstars want to come here, all the options are open!

    • cubtex

      Masterson has had 2 starts and the one where he really got pounded was by the Orioles(American League team) Let’s see how he finishes out the year before saying he couldn’t pitch for the Cubs.

      • Cubbiemacg

        Don’t agree too much with you Tex but today you have been spot on with everything.

        • cubtex

          blind squirrel :)

      • mutantbeast

        Masterson has a bad knee Tex, and hes never been as good as his numbers have sometimes indicated. Gets hit hard by lefties and his velocity is way down. I say dont even bother.

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  • BigJonLilJon

    My vote would be Lester. I don’t completely buy into Scherzer and he and Boras are going to want silly large money. I agree that spending the dollars and saving the prospects is the best idea.. certainly not doing both for 1 guy. Lester than another Hammell type would give us great options

    • cubtex

      and you think if Lester signs with the Cubs it will be a team friendly contract? Remember…he wanted to go back to the Red Sox but they thought he wanted more than what they wanted to pay him(which I am sure was a good chunk) If Lester signs with the Cubs it will be for big bucks that he will more than likely never live up to.

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

        I agree. It will be big bucks. But c’mon ST. You can’t tell me now, you’re going to be against signing FA’s? Lester will be a too big contract for too long. But that’s what it takes for a guy like that. And he will be very good for the first 3-4 years.

        • cubtex

          As I have always said…I have no problem signing big contacts and spending money as long as they act like a big market team. If they are holding back spending money(Until Soriano’s contract is off the books) (Until Zambrano’s contract is off the books) etc. Spend Spend Spend. That is what Theo has always done best.

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

            He should be very good when we do. But I think Theo has always been pretty good at stretching a dollar. Much more his style. From what I’ve read, all those later tenure big contracts like Gonzales and Crawford were mandated from ownership. In the end, those were some of the reasons he left. They wanted to make him go after and sign every big guy available and he felt there was a more efficient way to do things. Tito was with Theo too. Says a lot that the manager doesn’t want to throw big money at FA’s.

            Theo’s big FA signing was Matsuzaka. He very much wanted him. But if they hadn’t signed him they don’t win that second WS.

          • cubtex

            money helps. You can’t ever convince me that a high payroll doesn’t give a team an advantage. Boston has always had one of the highest under Theo.

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

            Oh it absolutely does. But Theo won in Boston by developing, drafting and signing. Look at guys like Coghlan he signed for us, and the pitchers that we’ve flipped like Maholm, Feldman and Hammel. And you see the roots of those sort of deals with guys like Papi, Mueller, Okajima and Foulke. Particularly Papi, who was a scrap heap pick-up. If that signing had happened yesterday, we’d have read on this site what a joke it was and how he would block Josh Vitters from achieving greatness! :)

            Theo does a great job regardless of pay. He’s just a guy with a feel for putting together baseball teams. He, Beane, Mozeliak and Friedmann are simply a cut above everyone else IMO.

          • cubtex

            Do you really want to include Keith Foulke? :) That was one bad contract.One of those backloaded contracts that TH says only Jim Hendry does. Papi was signed as a favor to Pedro Martinez. I thought you knew that history.

          • cubtex

            Among those keeping an eye on David’s contract status was Pedro Martinez of the Red Sox. The two had become close friends over the years. In fact, David viewed Martinez as a kind of father figure. When the Boston ace lobbied Theo Epstein to sign his buddy, the GM listended, offering David a one-year deal with a base salary of $1.25 million. With few options in front of him, David agreed

          • Tony_H

            You need to get your facts right, I have never said that JH is and was the only GM to back load contracts.

          • cubtex

            it needs to be done with teams that spend money. agreed. all big market teams do it.

          • Tony_H

            Agreed to what? Other GM’s do it and it is usually done by GM’s on the hot seat at the time trying to squeeze a player or 3 onto this years roster (to win now) and use future money (because they will likely be gone anyway).

          • http://chicagocubsonline.com/ Neil

            Tony, I just asked Ray to have conversations without calling someone out. Let’s move on from this.

            Thank you.

          • http://chicagocubsonline.com/ Neil

            Please have a conversation without calling someone out. Thank you.

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

            Foulke was key to 2nd title. May not have it without him. Probably likely they don’t. Same as Matsuzaka. If we win a title an a guy is a key contributor, I will sign him to 200,000,000/10 years an in year two he can break his leg and never be the same!

            And maybe that Martinez didn’t influence the Papi signing. I’ve never heard that. But I hope he did. If so that’s a cool story and says a ton about who Theo is as a person and GM. How many GM’s will listen to players about a signing? Trust their advice. I don’t think I’ve ever heard that before in MLB. Super cool.

          • cubtex

            you never heard of a gm appeasing the best player on the team by bringing in a friend of his before? I know you are a basketball fan…take a look at Lebron James. It happens in all sports.

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

            I’ve never hear it in baseball no. I still think its says a lot about Theo. Stories like that are what I find so endearing about him.

          • triple

            Kind of the reason to sign Gerardo Conception as well.

          • mutantbeast

            Board, Dice K was a nice pickup IF they had signed him for 4 years. His arm got burned out from overuse once he hit 30.

      • Jeff in Az

        I actually completely agree with Cubtex on this one.

        • cubtex

          wow. what is going on. I must be getting soft :)
          Cole Hamels is set to make 22.5 mil per year. Reports are that Lester is seeking 25 mil per for 5 years. 125 mil for 5 for Lester with all those innings under his belt doesn’t strike me as it being a good deal.

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

            Probably not, but who do you think they should get? I had thought Price was a FA but not until 2016. And I agree the Tigers will likely lock him up by then.

            I’d get Hammel, and I wouldn’t mind going after Francisco Liriano and a guy like JA Happ. Think Happ could be very good in NL.

            Then bide our time and see how our young bats progress. If by midseason we are in the race and Russell is up and raking. I think we could consider trading Castro or Baez Most likely Castro. I would prefer neither, but it’s an option.

          • cubtex

            I really have a hard time believing that Lester,Scherzer,Price will want to go to a team like the Cubs after having played for winning teams this year if other winning teams have similar contract offers. Cubs will have to blow teams away. As I said….Do It. Spend money and quit acting like a small market team. They have no big contracts and they have a lot of young controllable prospects that will be cheap for the next several years.

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

            I think the see the Cubs are right there though. Lester has already stated publically he likes what Theo is doing and would be incredible to be a part of it. Price said the same. Scherzer may be the outlier who would turn his nose up at the Cubs for whatever reason.

            But I think most baseball people, players, management, believe the Cubs are on the precipice of a long run of really great play. 2016 for sure, but next season if Arietta/Hendricks keep this up and we sign one of the FA’s. And of course, our young guys have to continue to produce. But I believe they will…of course I do :)

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

            I don’t think they’ll have to blow anyone away. Lester, for example, I believe would come to Chicago for less than he’d go to NY. I would imagine a lot of FA pitching will instruct their agents to place a call to Theo before they sign anywhere. Too much allure to being on that first Cubs team that wins. And too much excitement and hype about what we’ve got happening.

            Lester would probably love to have for his legacy being a part of championships with Red Sox and Cubs. How many guys can say that?!!?

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

            Honestly ST, I don’t think there’s too many people left that don’t think the Cubs are going places really soon. You’re about the only one left in that boat…:)

            Even the Cardinal fans are getting concerned supposedly. Somebody saw on one of their fan sites people commenting that what was happening with the Cubs was “not fair.” Cardinal fans saying that about us!

          • cubtex

            they will be good in another couple of years but honestly…do you think these guys would rather sign with a proven winner if the money is close….or a team that could be good IF the prospects all develop? It has to be about the Benjamins for the Cubs to get them.

            I am sure that most Cardinal fans are not concerned about what the last place team in the NL Central is doing. They are fighting for a division championship

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

            I don’t think you’re factoring the competition side enough. Professional athletes are incredibly competitive and have huge egos to fulfill. And I would venture to say that no athlete is as competitive as a MLB pitcher. These guys are nuts. Like fighter pilots. And I think that the challenge of the Cubs first series, combined with the positive steps underway, and the allure of Theo and his team. Players talk and share experience. Have you ever heard a big leaguer that once played on a Theo team ever say anything negative about the guy? Or how he treats his players and runs his teams? It’s known that in Boston he would hang out in the locker room and play cards with the “idiots,” and subsequent generations. He’s humble and just one of the guys. And he give his managers and coaches freedom. Players want to be in an environment like that.

            Add in that not too many people grow up hating the Cubs. There are us passionate fans, but outside of St. Louis, most people and fans hve nothing against the Cubs. I think that helps when guys think about their team of choice.

            And I don’t think we are as far away as you do. Even this year we have lost a ton if close games. You are who your record says you are I realize. But despite similar records, the talent and play of this years team is worlds ahead if last season. Pitching is the only real exception. And even them we’ve had right spots like Hendricks, Arietta, Ramirez, Strop and Rondon. Wada is looking good too. And all those are very young.

            I just don’t see us not much improved next year. If we acquire enough pitching I think we have a playoff shot. Alcantara and Baez are already up, adjusting and impressing. Castro and Rizzo are two of the leagues best, at any position. And Soler and Bryant are two of the more exciting prospects out there. Both more mature and ready than most at ther stage. They both could struggle, or just flop. But I think both will have big rookie years. And many analysts and writers agree. Could be 1, 2 in ROY. Then there is Russell, who also is viewed by most as close to a sure thing as there is, an capable i immediate impact. We’re not waiting on a bunch of super young guys to mature. These guys are mature, and look as ready as a prospect can look.

            I think most baseball people agree. And players. Price and Lester both have publically said they do.

          • cubtex

            didn’t your favorite Cub player struggle for 2 years? Most prospects will struggle. I think if I am Price or Lester and I am 30 years old…and a team that has been in the playoffs for the last several years and will continue to spend money and try every year to win regardless of cost offers me a contract(Anibal Sanchez for example) I am going to the proven winner. Of course…that is me

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

            Rizzo also had nobody around him. As a rookie he was basically put in meat of lineup and told “carry us.” That’s not fair and not good for development. But it is what it is. Soler and Bryant can both bat lower in order and have good bats to protect them. Rizzo had Soriano for a spell and that was it. Castro was never much help those first 1 1/2 seasons.

          • cubtex

            If I am a 30 year old pitcher…I am going to a team with proven vets that are one of the favorites to win the WS in 2015 not go to a team that will be breaking in prospects if the money is close. Now….if the money is substantially higher…..I will take my lumps for a while and grow with the prospects. In the words of Jerry McGuire….Show me the money!

          • Jeffrey Rogers

            Also, All of Soriano’s money is off the books as soon as the season is over. I believe it is the neighborhood of $15M. That is a big factor. That’s more than half of what it will likely take to get any FA pitcher they want.

            They will also have 2b, 3b, CF and probably RF being manned by guys making next to nothing. Also Hendrix will most likely be in the rotation, again making nothing.

            The team will be able to overpay for a TOR pitcher if they want to and not really get burned to bad if he flames out, because 1/2 the team will be 1st and 2nd year guys.

          • mutantbeast

            Mets would be a nice matchup. Wonder what it might take for Wheeler or Snydergaard.

          • Chris K.

            Hamels may be cheaper, but don’t forget he’s had some injury history. Started this season late due to arm troubles.

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

            True, but I think we could get a year or two out of him. He seemed to like it here and was cozy with Bosio…

      • Tony_H

        I agree it there will be no discounts, but all players say they want to stay where they are at…..until they get traded. I am sure Lester will check in with both the Red Sox and Cubs, but I don’t think for a minute he has decided where he will play or that he has eliminated any teams at this point.

      • mutantbeast

        My guess is Lester might take fewer yrs and a higher AAV. It might take about 4/100 to get him. Hes better than giving up the farm for Hamels.

  • TrevorPetersma

    I’m crossing my fingers we land a Lester plus another solid type pitcher in the offseason but I’m trying to keep my expectations down a little. There will my multiple suitors I’m sure, but hopefully this all pans out and next season is the year the W’s start flowing more freely.

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

    Love it! Great strategy I believe. Sign Lester, and make a trade for Hamels or similar. If we got both, we’re right in the thick of the hunt next season.

    Like Syndegaard, wouldn’t be upset if we traded for him. But prefer to keep our batters. To me Soler, Bryant, Russell are totally off limits. And I’m not including Baez, Castro or Rizzo because to me, at this point, they are obviously off limits.

    I’d prefer not to trade any of the next wave either. Almora, Schwarber, McKinney or Hanneman. If they want to look at the next wave I’d understand. And the Catarini, Vogelbach and Villanueva’s of the world I would absolutely trade. But I don’t see them bringing back Syndegaard. Thing is if we want Syndegaard, we need to get it over with, so he can go ahead and have his inevitable TJ surgery and start to rehab…

    • Jeff in Az

      Board- In my opinion there is no chance they sign Lester and Trade for Hamels. I could maybe see them signing Lester if it is the right price (as I stated in my other post) and more likely Masterson (maybe both Masterson and Lester if they really blow their wad).

      With the financial flexibility they finally have, I don’t see them using the prospects to get Hamels if they can sign Lester at a similar price and contract. I do however think that could change if in fact we can find a way to be competitive and in the hunt at the trade deadline next year. Then you may see a prospect deal for a guy like Hamels to add to the rotation.

      To get an established starter like Hamels in a trade from Philly you are going to have to give up a major league ready prospects and I’m talking some of those names we all have a man crush on (i.e. Russell, Bryant, or Baez). Names like Almora and/or Schwarber aint getting that deal done unfortunately.

      I do however appreciate your eternal optimism. Talk about the Cubs Faithful… :)

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

        I think you’re probably right Jeff. I just don’t think Theo wants to part with any of those batters. And I wouldn’t, as I stated above. Sign Lester, then resign Hammel or similar. Or sign Scherzer, but I don’t see them going that high.

        I think if we sign Lester, with Arietta and Hendricks behind him we’ll be pretty dang good. Then by end of season perhaps we have Black in the back of the rotation. And I think in 2016, we’ll see at least one of Edwards, Tseng, Underwood, Johnson ready to go. Most likely Johnson or Tseng. I know Tseng is lower than the others now, but I just have a feeling he’s going to be able to fly through…

        • J Daniel

          Theo may not want to part with any of them for sure. But Theo is ruthless and will do whatever he feels will make the club better. They are getting closer and need a couple of TOR pitchers.

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

            We will see. They do seem to like Syndegaard a lot.

            I don’t see Bryant, Rizzo or Russell ever being traded. I could see Castro, Baez and maybe an outside shot Soler. But I’d be shocked if Soler ever goes.

    • John_CC

      Rider, that 3rd wave of players: Zagunis, Torres, etc. are only legends in the making in your mind. No GM is considering trading a top SP for all of those guys! You’re calling a bunch of A+ players “untouchable.” That’s nuts. To acquire top talent you have to be willing to give up top talent.

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

        I realize that 3rd wave isn’t going to be traded for much now. Just saying I’d consider them.

        And untouchable is too strong. I’ll always answer the phone if it rings. But those top guys I would only trade for a proven, younger stud. Or a lopsided haul. Say Russell for 2 or 3 top AA pitchers. To me, at that age, bats are more valuable. Too many variables with pitching. Too many injuries. I’d need a multi-player pitching haul in return to give up Bryant, Soler, Russell, Castro, or Baez.

  • Jeff in Az

    My two-cents is that none of us should get to far ahead of ourselves with free agent signings. This Front Office has shown fiscal discipline (or flat out have no choice) in that they are not willing to overpay for any player. It is my opinion that they will not get in a bidding war for Scherzer. I do see them making a pitch to Lester but if history repeats itself it will be a take it or leave contract as far as dollars and years.

    This front office does like to try and catch lightening in a bottle (much like their predecessor Jim Hendry). That makes me agree with Neil on the Masterson front. We also can see that these guys like to stay with what they know and they drafted Masterson.

    I’m not saying that I wouldn’t love to have Lester or Scherzer in the Cubs rotation, I just think it is all speculation at this point. I see them going after Masterson because they can buy him on the cheap and then maybe swinging a deadline deal next year if they are actually in the wild card hunt. The worst Masterson does with the Cardinals, the better chance he is a Cub next year because Team Theo will send him to the University of Chris Bosio after signing him on the cheap.

    • cubtex

      alot will play out over the last 2 months. If Masterson turns it around,Cards do well in postseason and he likes his time with the Cards…he will probably not even be in play.

    • Larry Schwimmer

      Jeff, you make some great points and show some very good insight into THEO’s thinking. After all, how can any rationale GM spend $25+ million on a 6-7 year contract for a TOR pitcher and just forget about all the bad signings that have already been done by foolish GMs (e.g. Sabathia, Tanaka, etc.) Who wants to risk spending $25 million and then find out that your pitcher is going to be chronically on the DL or out for the season for a surgery.

      I have no clue why Scherzer refused a 6 year, $144 million dollar deal??? Maybe he just doesn’t want to play for Detroit? Otherwise, I say he’s just a greedy guy who could have an arm problem that could kill a big payday. How much more can you pay a pitcher? If I pay $25+ million I want someone as rare as Clayton Kershaw and even then I’d be very afraid of what might happen to his arm. There are 30 MLB teams. It only takes one desperate and foolish GM to sign an expensive, long-term deal. THEO will not be that G.M. He’ll come up with his best number for guys like Lester and Scherzer and they will accept it or not.

      If THEO can put together 5 good starting pitchers and we can some great offense together, the CUBS will be a contending team.

      • BillyFinT

        I agree with Jeff. The University of Chris Bosio nails it LOL.

        There’s also supply and demand. How will the Cubs compete via free agency depends on performance of the rookies into 2015.

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

      Good post brother…

  • mutantbeast

    Please, Theojed, stay away from Masterson. The guy your seeing thiis year has been on the verge of this years meltdown for several years. Cant retire lefties, hed be as frustrating as Zambrano was in his latest years.

    • cubtex

      bring back Z. Now that was good entertainment. Still remember the game when he plunked Edmonds on the hip the next at bat after he took him deep on purpose. He was must see TV :)

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

        Best idea in a while! :)

    • JasonOfTheBurbs

      agreed completely…he was a fantasy baseball disaster too.

  • JasonOfTheBurbs

    6 yrs 144 mill is stupid money, and scherzer should have taken it…he isn’t worth that.

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