Tagged: Jon Lester

Should Cubs’ Interest in James Shields Be Praised or Feared?

The Chicago Cubs are done adding pitchers with hefty price tags this offseason, but with the price tag on one free agent dropping down to more reasonable levels, the team could be pulling the trigger on a move after all.

That’s because rumors are flying that free agent pitcher James Shields could be on the team’™s radar, according to David Kaplan of CSN Chicago*.

For those that can’t read the tweet, here’™s the gist of Kaplan’™s argument: the Cubs have been waiting for the market to take shape for Shields, and it’™s becoming apparent at this point that he’s not going to get a contract worth more than $100 million this close to spring training. With teams preparing to report in two weeks (!), he’s looking to make a decision by the end of the week, and his history with Joe Maddon could make Chicago an attractive landing spot.

With those things in mind, a Shields signing would make perfect sense for the Cubs under the right parameters. If the deal is going to be in the three year range, the Cubs should jump on it and offer him as much money yearly as they want. A four-year deal would still work too, but going over $20 million per season would probably be a bit much.

The reason for an aggressive push if the term of the deal is right is simple: the Cubs don’™t have a ton of salary on the books for the next few years as some of their impact players have cheap deals. Guys like Kris Bryant, Javier Baez, Jorge Soler, and Addison Russell are all on really cheap deals during that time, and if two or three of them pan out as advertised (still a sizable if, but a much more reasonable thought than the notion that all four will be stars), having a guy like Shields added to the rotation could make the Cubs a serious contender during that time.

If Shields was paired up with Jon Lester and Jake Arrieta, the Cubs would have a rotation that would rival anything that an NL Central foe could throw out there, and they’d likely have one of the top five or six rotations in all of baseball. When coupled with the offense that the team is potentially going to have with guys like Miguel Montero added to the fold, and their dreams of making Back to the Future 2 could be much closer to reality than fans dare hope.

* = Kaplan is fairly plugged in with the Cubs, but he also has occasional misses (as do most reporters), so take this and all reports of activity on the North Side with a grain of salt.

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Cubs Introduce Lester: Five Things We Learned Monday

The Chicago Cubs trotted out their biggest free agent acquisition in nearly a decade on Monday as they introduced Jon Lester to the media.

You know the numbers (6 years, $155 million, $30 million in signing bonuses), but if you didn’t watch the press conference, here are the five most important things we learned about what the Lester signing means for the Cubs.

Lester Hungry for New Challenge

The Cubs’ sales pitch was much different than that of the Boston Red Sox or San Francisco Giants. While those teams could point to past results (Red Sox) or the fact that they have won World Series in three of the past five seasons (Giants), either one of the destinations would have been a safe one for Lester to go to.

As for the Cubs, their pitch was that they are on the verge of something great, but sometimes that isn’t enough to convince a free agent to come to town (see: Masahiro Tanaka). For Lester, it was.

“I believe in the plan they have in place for the future of the Cubs,” Lester said of Theo Epstein and Jed Hoyer. “Leaving a place you’ve already won is difficult, but also relishing the chance of winning a World Series in a place that never has adds that little extra for me.”

Lester’s grasp of history isn’t quite where it should be (the Cubs have won two World Series titles), but his heart is in the right place.

Epstein Feels that Rebuild Was “Quick”

While the last three years have felt like an eternity for Cubs fans, it hasn’t felt like that long of a process for Epstein.

“It’s been a pretty quick rebuild,” Epstein said. “It wasn’t perfect, but thanks to a lot of the good decisions in the draft and trades, and the hard work of our scouts and our player development, we had a competitive team on the field (toward the end) of 2014. If it weren’t for those things, I don’t think Jon Lester would be choosing the Cubs.”

Epstein did also thank Cubs fans for their patience, but the point is clear. He looks at the whole rebuild as a long-term process, and three years really feels like a drop in the bucket compared to the long-term success that he envisions for the team.

Theo, Cubs Occasionally Do Appreciate the Role of Tradition

The Cubs are a tradition-rich team, and while you may be forgiven for thinking that they’ve been ignoring that tradition in recent years, thanks to new signage all over the ballpark and the big renovations occurring, there is still an element that persists in this front office.

When Lester was introduced to the media on Monday, he was given a jersey with the number 34 on it. Lester says the jersey was meant to honor Walter Payton and Nolan Ryan, but it also immediately brought up memories of Kerry Wood, who struck out 20 batters in a game while wearing the number.

According to reports, Epstein texted Wood and asked him for his blessing to use the number, and the former Cubs hurler said he would be “honored” for Lester to wear it.

Kudos to Wood for agreeing to it, and kudos to Epstein for reaching out to the pitcher about using the number. It wasn’t a requirement by any stretch, but it was a nice gesture.

Samardzija, Hammel Played a Role in Recruiting Lester

The Cubs may have traded away Jeff Samardzija and Jason Hammel during the regular season, but even while they were in Oakland they played a role in selling Lester on the benefits of playing in Chicago.

“I asked a lot of questions to a lot of different guys about different teams and organizations, and I wanted to get their feel for Chicago and what made them happy here,” Lester said. “They weren’t the only guys I questioned, but obviously playing with them I had the privilege of talking to them more often about it.”

Now, both players are back in Chicago along with Lester, although Samardzija will be plying his craft on the south side with the White Sox while Hammel returns to the Cubs.

Love of Hunting Bonded Lester, Ricketts

While Joe Maddon bonded with Epstein and Hoyer at an RV park in Pensacola, Florida, Cubs majority owner Tom Ricketts used a different tactic: talking to him about hunting.

According to Epstein, Lester and Ricketts discussed the sport at dinner in Chicago while the team was courting the free agent pitcher. Epstein also added the helpful mental image of him soaked in deer urine, which he said he was willing to do if it meant that he would land Lester.

Cubs vs. White Sox: Who Has Had the Better Offseason?

If there has been a dominant theme at baseball’s Winter Meetings over the past few days, it’s been tinged with blue stripes and red stars. The city of Chicago is absolutely holding court on one of MLB’s biggest stages, with both the Cubs and the White Sox addressing major needs and making huge splashes all over the place.

Now, with the Winter Meetings close to concluding, we have an opportunity to evaluate where each of the teams stands in terms of their offseason to-do lists. Which one is having the better time of restructuring their roster? Let’s find out.

Addressing Needs – Edge: White Sox

The Cubs came into the offseason needing to add a top of the rotation pitcher, and they also wanted to add a different, more defensively proficient catcher to the mix. They’ve done both of those things, signing Jon Lester to a rich contract and trading for Miguel Montero from the Arizona Diamondbacks.

While they will still be making moves as the offseason wears on, the White Sox have done a better job of addressing more of their needs. Right-handed pitcher to slot between Chris Sale and Jose Quintana? Done. Relief pitchers to shore up a horrendous bullpen? Done and done. A left-handed bat to help protect Jose Abreu in the lineup? Done.

The Cubs have really done a great job of addressing some of their needs, but Rick Hahn has really done some great work in shoring up the Sox roster.

Star Power – Edge: Cubs

While names like Adam LaRoche and David Robertson certainly move the meter in terms of what they can do for a team, they are no match for the talent that the Cubs have brought in. Montero is a pretty big name (at least from a catching perspective), but Lester was the top of the heap in terms of available pitchers, and landing Joe Maddon went a long way toward showing the baseball world that the Cubs mean business.

Bang for Your Buck – Edge: White Sox

The Cubs shelled out a ton of money for both Maddon and Lester, and the White Sox really paid a ton for Robertson to come protect the back end of the bullpen. They did get some really nice value in signing LaRoche for two years, but the one that’s most intriguing is adding Zach Duke for $5 million per season. He could be an excellent eighth inning guy, and the Sox could presumably use him in closing duty if Robertson is injured or needs a day off.

Having that kind of an arm in the bullpen is a huge asset, and while neither team has been particularly frugal this offseason, the Sox hold a narrow edge.

Long-Term Impact – Edge: Cubs

The Sox made a big move by trading for Jeff Samardzija on Monday at the Winter Meetings, but there is no guarantee that they will be able to sign him to a long-term extension before he hits free agency after the 2015 season. LaRoche is also signed for just two years, and while Duke (three years) and Robertson (four years) are signed for slightly longer, none of them figures to be a player that the White Sox build themselves around for the next five or more years.

On the other side of town, the Cubs’ additions have the potential to be those kinds of cornerstones. Of course, you get what you pay for in that regard, with Lester being signed for seven years, but the real thing that pushes this category into the Cubs’ column is Maddon. Adding him to the mix not only signals a seriousness of purpose on the part of the north siders, but it also means that the team will be able to get the most out of the young players working through their system, and by proxy means he’ll make a larger long-term impact than any other acquisition by either team this offseason.

Overall – Edge: Cubs

Both teams have made big splashes and important moves that have them poised to be a lot better in 2015, but we have to give the narrow edge to the Cubs in terms of the quality of their offseason. Maddon and Lester are a formidable combo that is tough to beat, but the White Sox and their additions of Samardzija, LaRoche, and Robertson do come very close.

It’s a tight race, but it looks like the north siders win by a nose.

With Lester in the Fold, What is Next for the Cubs?

If Theo Epstein and Jed Hoyer had drawn up a wish list before the offseason began, Jon Lester would have likely been at the top of it. On Tuesday night, they were able to add a check mark next to his name, signing Lester to a six-year deal worth a reported $155 million.

 

The news came as a delightful surprise to Cubs fans who were preparing themselves for the worst, waiting for the Boston Red Sox or San Francisco Giants to swoop in and grab Lester out from underneath them. Instead, an offseason that began with the Cubs bringing in Joe Maddon to be their manager has hit a crescendo with the biggest name on the free agent pitching market heading to the north side.

 

The question now is a simple one for the Cubs: what comes next? The team has already addressed some of their biggest holes, adding a top of the line starting pitcher in Lester, bringing in more rotation depth with Jason Hammel, and bringing in an excellent defensive catcher in Miguel Montero. Other players from the minor league system will certainly be on the way to plug holes, with Kris Bryant likely joining Javier Baez and Jorge Soler sooner rather than later at the big league level.

 

All of those things are great, but there is still work to be done. Some reporters, including Ken Rosenthal, believe that the Cubs will continue to pursue a big veteran bat to add to their lineup. Whether that means trading for a big-name player like Matt Kemp or Justin Upton, or signing another free agent like Chase Headley, the Cubs could look to accelerate their rebuilding process even more than they already have by acquiring another bat.

 

Outside of making another big splash, there are still plenty of areas where the Cubs could shore up their roster. Adding another starting pitcher wouldn’t be out of the question, so a guy like Justin Masterson could be an interesting player to keep an eye on. He would likely come cheaper than some other options, and he would add more competition in a rotation that is already significantly deeper than it was over the past few years.

 

The Cubs could also be looking to move a starting pitcher or two in order to bring in other pieces. Travis Wood could be one of the guys moved, as he would likely yield a nice return in the event of a trade. He would also provide a really nice third or fifth starter for the Cubs, depending on where they would like to slot him, and so Epstein and Hoyer would have to make a tough choice in that regard.

 

Moving Edwin Jackson’s contract will also be a key thing for the Cubs to do. It will likely mean taking on another contract that a team is looking to unload, but if the Cubs could find the right trade partner, they could turn arguably the biggest mistake of the Epstein/Hoyer regime into less of a misstep.

 

The Cubs are obviously not where they want to be as an organization, but they are quickly making their way in that direction. With a new manager, a huge free agent acquisition, and a major trade, they have made massive strides toward competing in 2015, and with some more tweaks and additions, they could be poised for an even bigger leap toward World Series contention than they are at the moment.