Jon Lester

Jon Lester: The most important signing in Cubs history

Jon Lester: The most important signing in Cubs history

Jon Lester became the most important signing in Cubs history when he agreed to a six-year, $155 million contract to be the ace of the Cubs.

He spurned his old team — the Red Sox — along with a handful of other teams ready to pony up the nine-figure deal necessary to acquire the frontline starter. By choosing the Cubs, Lester accelerated Theo Epstein & Jed Hoyer's famous "Plan," legitimizing Chicago as a free agent destination and as an up-and-coming perennial playoff team.

"This signing really marks a transition of sorts for the Cubs, the start of a period where we are clearly very serious about bringing a World Series to the Cubs and the people of Chicago," Epstein said back on Dec. 15, 2014.

Inking Lester to a megadeal was a calculated risk, but all $100 million contracts are. Here's a closer look at the Cubs 100 million dollar men:

Nov. 30, 2006 - The Cubs introduce Alfonso Soriano

Back in 2007, the Cubs needed to make a splash and did so by signing the top free agent hitter on the market.

The Cubs inked Alfonso Soriano to an eight-year, $136 million dollar contract — then, the largest in franchise history. The Cubs had their leadoff hitter — fresh off becoming the fourth member of the 40-40 club — to go along with a new manager in Lou Piniella. Soriano made two All-Star teams for the Cubs in 2007 and 2008 while playing a key role on both division-title winning teams.

However, his time with the Cubs will often be remembered by his offensive decline, his subpar play in the outfield, and his eventual trade to the Yankees. While his overall body of work was statistically respectable, his output did not match the $136 million the Cubs invested in him.

Dec. 15, 2014 - The Cubs introduce Jon Lester

Like the signing of Soriano, the reeling in of Lester to Wrigley Field was paired with the hiring of another new big name manager, Joe Maddon.

Three years into his megadeal, Lester is 43-25 with a 3.33 ERA in 96 starts. The 2016 All-Star and Cy Young runner-up has done some of his best work in the postseason, where he's 3-1 with a 1.98 ERA in his last nine postseason appearances — three of which came in the 2016 World Series.

Lester's tireless work ethic off the field and his veteran influence in a young Cubs clubhouse has made this signing a smashing success. 
    
Dec. 15, 2015 - The Cubs introduce Jason Heyward

One year to the day after introducing Lester, Jason Heyward met with the Chicago media after signing an eight-year, $184 million contract — the richest in franchise history.

Heyward was coming off one of his best offensive seasons (.289, 13 HR, 60 RBI with the Cardinals) and his third Gold Glove in four seasons but the prized free agent struggled from the start in Chicago. Taking Heyward away from the Cardinals and signing baseball's top free agent prize ended up creating an outfield log jam in Chicago.

Heyward's speech during the rain delay in Game 7 against the Indians will most likely end up being the highlight of his Cubs career. The post-World Series championship offseason storyline of Heyward rectifying his broken swing was entertaining to follow on social media, but his 2017 slash line of .259/.326/.389 is clearly not worth the $184 million he signed for.

The future is now

"I believe in the plan that they have in place for the future of the Cubs."

That's what Lester said back on Dec. 15, 2014.

That statement still holds true today. Lester remains the anchor of the Cubs staff surrounded by Kyle Hendricks and Jose Quintana with reinforcements on the way. Regardless of any additions or subtractions, the Cubs will again be one of baseball's World Series favorites entering 2018 and the reliable lefty will be at the center of it all.

Halfway home, the $155 million deal has been "smart money" spent on Lester, the most important signing in Cubs franchise history.

Cubs 2018-19 pitching staff coming into focus

Cubs 2018-19 pitching staff coming into focus

Wade Davis still hasn't signed anywhere, but the Cubs have added more bullpen reinforcements while their former closer decides his future.

The Cubs are still looking for another starting pitcher and very well may be open to another reliever — whether that be Davis or not is still to be determined.

But with more than 10 days left until Christmas — a checkpoint for most free agents as they want to kick back during the holiday with family knowing where they're going to play in 2018 — the Cubs' pitching staff is taking shape with Steve Cishek now in the fold.

If the season started today, here's how the staff may look:

2018 rotation

Jon Lester
Kyle Hendricks
Jose Quintana
Tyler Chatwood
Mike Montgomery

2018 bullpen

Brandon Morrow (closer)
Carl Edwards Jr.
Pedro Strop
Steve Cishek
Justin Wilson
Justin Grimm
Dario Alvarez

Montgomery will serve as a starter at some point in 2018 even if the Cubs sign another guy. The team will either go with a six-man rotation at some point or somebody will end up on the disabled list. Injuries happen and the Cubs are hoping to play into the final week of October this year, so rest assured, they will absolutely be conservative with their starters' innings once again.

Theo Epstein and Jed Hoyer admitted if the season started today, Morrow would be the closer. Beyond that, they acknowledged there are very few moves they could make to bump Morrow out of ninth-inning duties (though re-signing Davis would be one such move).

The Cubs will also likely go with eight relievers for much of the 2018 season with a position player group packed with versatile guys that can play multiple positions and switch-hitters. Dillon Maples may be a guy that finds his name in the bullpen mix if he can harness his control.

Cishek is another quality signing, adding even more depth in the late innings and high-leverage situation. The 31-year-old veteran has 121 career saves and can slot in as a closer if need be, though Joe Maddon also thinks Edwards and Strop can do the job and Wilson was one of the game's best closers before he hit a rough patch the final two months of 2017 in Chicago.

The Cubs' moves this winter have helped stablize the pitching staff beyond 2018. Chatwood, Morrow and Cishek are all signed under multiyear deals while Drew Smyly was also inked to a deal through 2019 as he rehabs from Tommy John surgery.

Here's how the 2019 pitching staff looks right now:

2019 rotation

Jon Lester
Kyle Hendricks
Jose Quintana
Tyler Chatwood
Drew Smyly

2019 bullpen

Brandon Morrow (closer)
Carl Edwards Jr.
Steve Cishek
Mike Montgomery
Justin Grimm

(Pedro Strop has a team option for the 2019 season.)

Thanks to Quintana's affordable contract, the Cubs only have around $77 million committed to the pitching staff in 2019 (plus arbitraion for Hendricks and Montgomery), so they have the flexibility to add even more depth and talent in the run prevention department.

The 3 biggest Cubs questions as MLB Winter Meetings kick off

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USA TODAY

The 3 biggest Cubs questions as MLB Winter Meetings kick off

LAKE BUENA VISTA, Fla. — As the baseball world descended upon Disney World, the Cubs are sitting pretty.

Theo Epstein's front office is poised to make "The Happiest Place on Earth" a reality as they already appear to have some of their major offseason issues resolved.

The Cubs reportedly have an agreement in place with late-inning reliever Brandon Morrow, a move that should be announced Monday once a physical is passed, the "I" are dotted and the "T"s are crossed. 

Couple that with last Thursday's signing of starting pitcher Tyler Chatwood and the Cubs' search for pitching has gone well even if they missed out on 23-year-old Japanese sensation Shohei Ohtani.

However, while the Cubs are in an enviable position of filling most of the pressing holes on their roster entering the MLB Winter Meetings, there are still questions to be answered.

Here are the top three questions facing Theo and Co. in Florida this week:

1. Who will fill the final rotation spot?

The Cubs are said to be pushing hard for Alex Cobb to fill out their starting staff, but as of the official tipoff of the Winter Meetings, no deal had been reached.

Cobb and the Cubs have been linked since before the right-hander even reached free agency. There was a clear need for another starter on Chicago's North Side heading into the winter and Cobb had the connection with Joe Maddon from their days together in Tampa Bay.

Cobb's connection to the Cubs was strengthened when Maddon hired former Rays pitching coach Jim Hickey to serve in the same role in Chicago.

If the Cubs are able to secure Cobb's services, they will have their starting rotation set for 2018:

Jon Lester
Kyle Hendricks
Jose Quintana
Alex Cobb
Tyler Chatwood

Depending on the length of the deal for Cobb, the Cubs could have some rotation consistency for the next several seasons as all four current starters (Lester, Hendricks, Quintana, Chatwood) are signed through the 2020 season.

However, if the Cubs and Cobb can't come to an agreement — they are hardly the only team bidding on the 30-year-old's services — who will be the fifth and final starter? The free agent market is rather slim after Cobb, Jake Arrieta and Yu Darvish, though the trade market is clearly an option with the Cubs currently possessing a surplus of young position players.

2. Will the Cubs pull off any major trades?

There's no doubt the Cubs will be linked to plenty of trade rumors throughout the week at Disney World, but will anything actually come to fruition?

Kyle Schwarber has been linked to a pair of American League East teams — the New York Yankees and Boston Red Sox — over the last few days, but it'd be tough to see the Cubs sell low on a guy they absolutely love.

Forget the fact that he's lost a bunch of weight and in the best shape of his life (which does matter if he's to improve his range in the outfield), here's how Epstein explained why the Cubs feel such a personal attachment to America's Now-Not-So-Large Adult Son:

"I will say that it's really an organization-wide evaluation of this player," Epstein said the day after the Los Angeles Dodgers eliminated the Cubs from the NLCS in October. "But I'm not skirting responsbility. I'll happily endorse him. He's the type of the player that we want to win here with the Cubs and have won with. 

"The fact that he hit 30 bombs in a bad year is a good start. But power is not everything. I think he fell into this year becoming a little bit more of a slugger and less of a hitter than he really is. That's important for him to get his identity back as a hitter, as a dangerous hitter that honestly, we feel he has the potential to be an all-around hitter on the level of Anthony Rizzo, per se. 

"When he reaches his prime, I think we feel like that's what he could be. He's got certain toughness and certain leadership qualities that are hard to find that we don't necessarily have in surplus in abundance running around in this clubhouse and organization. Certain energy and grit and ability to bring people together. That's important. We rely on it. But the biggest thing is his bat. We think he's the type of offensive player that you build around along with a couple other guys like him."

You'll be hard-pressed to find a better public endorsement of any player from Epstein.

But even if Schwarber isn't dealt, the Cubs can still trade any number of guys from a pool that includes Ian Happ, Albert Almora Jr., Javy Baez or Addison Russell.

3. Will Morrow have any other new bullpen mates?

Assuming Morrow's deal doesn't hit any snags, will the Cubs add any other relief reinforcements this week?

It's a pretty good bet to take. Never in the history of baseball have relievers had such an impact on important games — particularly in October — and the Cubs clearly understand that as well as anybody.

After Maddon's mix-and-match approach with the bullpen the last two postseasons, the Cubs clearly cannot go into 2018 with World Series expectations when they boast essentially the same relief corps, with Morrow replacing Wade Davis.

Speaking of Davis, the presence of Morrow doesn't necessarily mean the 2017 Cubs closer with "huge balls" won't be returning. Morrow's reported $10+ million per year makes a Davis return less likely, but the Cubs certainly need another impact reliever and Morrow can slot in as a seventh/eighth inning setup guy.

Here's how the Cubs bullpen depth chart looks right now (with Morrow inserted):

Brandon Morrow
Carl Edwards Jr.
Pedro Strop
Mike Montgomery
Justin Wilson
Justin Grimm
Dario Alvarez

Plenty of high-leverage relief options remain available on the open market, including Brandon Kintzler (whom the Cubs were linked to this week), Addison Reed, Anthony Swarzak, Jake McGee and Bryan Shaw.