Why Theo Epstein almost reached the breaking point and sold pieces off this Cubs team


Why Theo Epstein almost reached the breaking point and sold pieces off this Cubs team

Divided, tone-deaf, gridlocked, the Cubs reflected Washington the last time they played at Nationals Park, where veteran catcher Miguel Montero went rogue during an epic postgame rant and the defending World Series champs kept stalling around the .500 mark.

Team president Theo Epstein watched the Nationals run wild across his iPad on June 27 while he was visiting the Class-A Myrtle Beach affiliate, a breakdown that had Montero pointing the finger directly at Cy Young Award winner Jake Arrieta for those seven stolen bases.

Within seconds of seeing those explosive comments in his South Carolina hotel room, Epstein knew he wanted to get rid of Montero, who couldn’t hide his frustrations with manager Joe Maddon…during a radio interview the day of the championship parade and Grant Park rally last November.

Montero wasn’t exactly a lone wolf, speaking out for players who didn’t always see the communication skills that Maddon showed off during his media sessions. Even Arrieta appreciated Montero’s honesty, saying: “I love Miggy.”

Looking for a button to push with a team that wasn’t getting a jolt from The Cubs Way culture or Maddon’s laissez-faire style, Epstein DFA’d Montero and eventually shipped him to the Toronto Blue Jays.

The next day, about half the team showed up at the White House, where board member Todd Ricketts told Donald Trump the Cubs would run into the Nationals in the playoffs and predicted: “You’ll see them crumble.”

In reality, the Cubs were dangerously close to imploding, which will make it fascinating to watch which team crumbles during the best-of-five National League Division Series that begins Friday night in Washington.

As Epstein consulted with a few players about the Montero decision, he sent this message: Get your stuff together and play with an edge if you want us to trade the Class-A talent here in Myrtle Beach for big-league reinforcements this summer.

The Cubs also quietly put the word out to teams looking for starting pitching and bullpen help: There was a remote possibility that looming free agents Arrieta and Wade Davis would be available at the July 31 trade deadline. A new collective bargaining agreement – with the international spending restrictions, luxury-tax implications and a modified qualifying-offer system – would have been part of the rationalization.

“Not blowing it up,” Epstein said. “But when you’re five-and-a-half out, if you have a bad road trip and a bad homestand and then you’re 10-and-a-half out, absolutely, we would have sold.”  

[MORE CUBS: How Jon Jay brought Cubs clubhouse together for big finish]

That’s the deficit the Cubs faced on July 9, when Jon Lester got rocked during a 14-3 loss to the Pittsburgh Pirates at Wrigley Field that left the defending World Series champs with a 43-45 record. During that final game before the All-Star break, Epstein received a text message from White Sox general manager Rick Hahn, sparking the Jose Quintana trade talks.

Davis – who wasn’t even a part of last year’s championship team – would be the only player representative at the All-Star festivities in South Florida. Epstein went into stealth mode that week – credit Reddit users Wetbutt23 and KatyPerrysBootyHole with the scoop – and gave up top prospects Eloy Jimenez and Dylan Cease in a blockbuster deal for Quintana that would solidify the rotation through 2020.

Epstein left his family’s beach vacation in Massachusetts to join the team at Oriole Park at Camden Yards, where he got his start in professional baseball as a summer intern out of Yale University in 1992, the same year that trendsetting stadium opened in downtown Baltimore.

Epstein noticed the mood in the visiting clubhouse after that first game back from the All-Star break on July 14 – a 9-8 victory where the Cubs got homers from Willson Contreras, Kyle Schwarber, Ben Zobrist, Jason Heyward and Addison Russell, still almost blew an eight-run lead and began a six-game winning streak.

“In the first half, we were kind of tired of the postgame celebration,” Epstein said. “It was getting kind of old.

“Folks don’t understand. Once you win it all – and you’ve given everything you’ve had – the specter of playing 162 games and making them all meaningful is really overwhelming. It’s hard to get up for all of them.

“The first half, there were just a lot of things, different gripes going on. It was kind of more a collection of individuals than it was anything else.

“And then as soon as we hit the break – and we had to answer the bell – our guys did. We came back from the break as a team – and as a really good team – and we celebrated that win like it was a postseason win.

“We took off from there. That vibe of a loose atmosphere – but very connected group – was back. And we kind of rode it the whole second half.”

The Milwaukee Brewers, a rebuilding team with an Opening Day payroll around $56 million, spent 69 days in first place, but never after July 25. Epstein’s front office never got to the point of exchanging names or discussing any white-flag deals in depth or really considering a breakup of their young core. But the Cubs now believe that adversity will make them stronger in October.

“Look, it was crunch time early this year,” Epstein said. “If we had had a bad road trip and a bad homestand to start the second half, we’re selling. We didn’t. We started to play pretty good baseball right off the bat. We added and our guys elevated their level of play and had a hell of a second half and a great closing kick.

“And now we’re going into the playoffs with as much momentum as anybody.”

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.