After making blockbuster Aroldis Chapman deal last year, how aggressive will Cubs be at this trade deadline?

After making blockbuster Aroldis Chapman deal last year, how aggressive will Cubs be at this trade deadline?

The New York Yankees operated in an ideal seller’s market last summer, beginning with the iconic team with the 108-year championship drought, a stash of young blue-chip talent and a front office that’s never afraid to think big.

Cubs president Theo Epstein put it this way after making the blockbuster deal for Aroldis Chapman: “If not now, when?”

The Cubs wanted the parade down Michigan Avenue and got maybe one of the largest gatherings in human history, generations of fans flooding the streets of Chicago last November and spilling into Grant Park. 

For a moment late Friday afternoon, Chapman stood alone on the Wrigley Field mound after beating Javier Baez with a 100.4-mph fastball. That helpless foul tip ended New York’s 3-2 comeback win over the Cubs, another reminder of Chapman’s intimidating presence on the day he got his World Series ring, a Rage Against the Machine tribute on the video board and hugs from his ex-teammates.

What about the trade deadline now that the Cubs are no longer on the greatest quest in professional sports?

“I don’t think the urgency changes,” general manager Jed Hoyer said. “The goal is to win every year. I do think that the team last year – their play almost demanded us to be aggressive. We came out from Day 1 and we played like the best team in baseball.

“We were pitching well, hitting well, blowing people out and felt like that team had one Achilles’ heel – the back of the bullpen. And given where we knew we were going in the playoffs, we needed that guy.”

The resurgent Yankees (18-9) were down to their last strike when Brett Gardner blasted a Hector Rondon slider into the right-field patio deck for a three-run homer, but that moment didn’t necessarily reveal deeper issues within the bullpen.     

Wade Davis – zero runs through 13-plus innings and 7-for-7 in save chances as a Cub – had already worked three days in a row. Rondon, a one-time 30-save closer, entered the ninth inning with a 1.59 ERA. Pedro Strop screamed and punched the air after striking out Aaron Judge looking at a slider to end the eighth inning. Carl Edwards Jr. (0.69 ERA) continues to look like someone who could handle that Andrew Miller hybrid role.

“I don’t want to say forced our hand (last year),” Hoyer said, “but with the way they played it was clear that this was a team to be really aggressive for. I think every year you have to feel that out. You have to get a sense of your club.

“Obviously, it’s too early to have a sense of this club. But last year, give them credit, they went 25-6 out of the gate and they made it really clear this was a year to be aggressive.”

The Cubs are 16-13 and leading a division that doesn’t have any other superpowers and playing in a National League that doesn’t look quite as intimidating with the New York Mets and San Francisco Giants already in damage-control mode.

On Cinco de Mayo, it’s impossible to say exactly what the Cubs will need by July 31. But the Cubs conserved resources for that deadline and also have a pretty good idea of what their everyday lineup will look like through the 2021 season, which made elite prospect Gleyber Torres available in the Chapman deal and means someone like Ian Happ could be dangled in a trade for pitching.  

With Jake Arrieta and John Lackey positioned to become free agents after this season – and Brett Anderson taking a 6.23 ERA into Saturday night’s start against the Yankees – the Cubs could be looking at a 60-percent turnover rate for their 2018 rotation.

“You can’t get in a cycle where you’re always doing something for rentals,” Hoyer said. “But at the same time, every season is sacred and you only have (so many chances). There are going to be years where things don’t come together, you have injuries, another team runs away with it. That’s going to happen. So when you know you’re in a good position, (go for it).”

That’s why Torres – who entered his age-20 season as Baseball America’s No. 5 prospect – could become a star in New York and the Cubs will never have any regrets about that 4-for-1 Chapman trade.

“I’m always confident in Theo and Jed,” manager Joe Maddon said. “We gave up a lot. The kid we gave up is very good. However, to win a World Series, I think you do it like 11 out of 10 times.”

Cubs reportedly interested in adding Yu Darvish to starting rotation


Cubs reportedly interested in adding Yu Darvish to starting rotation

The Cubs aren't expected to bring back Jake Arrieta. But what about adding the other top pitcher on the free-agent market?

According to a Saturday report from The Score's Bruce Levine, the Cubs are showing interest in Yu Darvish, who they recently saw in the National League Championship Series against the Los Angeles Dodgers.

Darvish joined the Dodgers in the middle of last season after spending five and a half years as a Texas Ranger. He pitched Game 3 of the NLCS against the Cubs, holding that unusually cold lineup to just one run in 6.1 innings at Wrigley Field, helping the Dodgers reach the World Series. Darvish pitched twice in the Fall Classic against the Houston Astros, taking losses both times and twice failing to get out of the second inning against his old division rivals, including in the decisive Game 7.

The 31-year-old Darvish has been excellent since coming over from Japan ahead of the 2012 season. He's been named to four American League All-Star teams and finished in the top 10 in AL Cy Young voting in each of his first two seasons. He missed the entirety of the 2015 campaign with an injury.

Darvish has a 3.42 career ERA in his five big league seasons and three times has struck out more than 200 hitters in a season, including a baseball-leading 277 in 2013.

Along with Arrieta, Darvish is expected to fetch a huge payday this offseason. The Cubs' reported interest could show that they're not finished adding to their pitching staff despite signing four arms in recent weeks. Tyler Chatwood was a free-agent addition to the starting rotation, bringing the number of spoken-for spots there to four, with Chatwood joining Jon Lester, Kyle Hendricks and Jose Quintana as rotation locks. Brandon Morrow and Steve Cishek were added to the bullpen, while Drew Smyly — who's expected to miss the entirety of the 2018 campaign while recovering from Tommy John surgery — was signed with eyes on 2019.

After Mike Montgomery's desire to be a starter or go somewhere where he could be was reported during the Winter Meetings, there was a thought he could be the answer at the No. 5 spot on the starting staff. But this reported interest in Darvish — not to mention the team's previously reported connections to free-agent starter Alex Cobb — could mean the Cubs are still looking to add a big name to make the rotation more closely resemble what it looked like in recent seasons with Arrieta in the mix.

The Epstein's front office certainly has options, and the team has frequently voiced its confidence in Montgomery as a starter. But the team, for all its additions, has yet to make a splash this offseason. Stay tuned.

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.