How Cubs wound up spending big on Jason Heyward


How Cubs wound up spending big on Jason Heyward

“No,” Theo Epstein said, he didn’t see the Cubs being able to do two deals in the $100-million range this offseason. “You can pretty much apply that one going forward, at least until we get a TV deal, and probably beyond…that’d be a big winter.”

This was Nov. 9, the beginning of the general managers meetings, when the idea of signing Jason Heyward to an eight-year, $184 million megadeal – without cutting corners everywhere else on the roster and handcuffing future Cubs teams – sounded like a fantasy.

Dressed in a T-shirt, gym shorts and sneakers, Epstein had just finished a workout when a few Chicago writers stopped him near the registration desk of the Boca Raton Resort & Club. The president of baseball operations had brought his wife to South Florida and looked and sounded like he would rather be anywhere else on the waterfront property than a hotel lobby crawling with reporters and agents.

Epstein has a law degree and always chooses his words carefully, but this wasn’t a misdirection play, because other teams always think the Cubs are playing with Monopoly money anyway. Epstein also has a wicked sense of humor, but he wasn’t trying to punk the media, because it’s always been in his best interests to explain The Plan.

The calculus changed within the last few weeks, leading up Friday’s reports that Heyward had turned down $200 million offers elsewhere. A payroll picture that looked murky on Sept. 1 or Oct. 1 or even the middle of November came into sharper focus before the winter meetings at Nashville’s Opryland complex.

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Epstein and general manager Jed Hoyer pried open the franchise’s financial black box, working with chairman Tom Ricketts and Crane Kenney’s business operations department to grab money generated during a surprising run to the National League Championship Series.

The Cubs would reinvest in a team that has: two more seasons before Jake Arrieta hits the free-agent market; a ticking time bomb in Jon Lester’s $155 million contract; and no stud pitching prospects anywhere close to making The Show.

Next winter’s class of free agents also didn’t look very appealing, so the Cubs wanted to binge this offseason instead of throwing money at the wrong players.

For years, the Cubs have been a rigid, conservative operation, limited by the leveraged partnership between the Ricketts family and Sam Zell’s Tribune Co. (in a deal that included a piece of Comcast Sportsnet Chicago). The big-market spending power would only be back in full force with the anticipated launch of a new Cubs channel in 2020 (assuming the cable bubble doesn’t burst before then).

A front office that sometimes tends to overthink things absolutely pounced on big-game pitcher John Lackey, super-utility guy Ben Zobrist and Heyward, bankrolled by a business side that got good reviews for Wrigley Field’s Video Board Era after initially handling the rollout of the restoration plan in such a clumsy manner. 

Whatever business vs. baseball tensions exist, the Cubs just dropped $272 million on Heyward, Lackey and Zobrist, taking two valuable players away from a 100-win St. Louis Cardinals team, trading former All-Star shortstop Starlin Castro to the New York Yankees and getting creative with the structure of those contracts.

[MORE: Heyward signing reinforces World Series expectations for Cubs]

Even if you get The Plan, this is still a stunning transformation for a franchise that hasn’t won the World Series since 1908 and finished in fifth place every season between 2010 and 2014.

Cubs fans burned by overhyped prospects before can now watch Rookie of the Year Kris Bryant play here through the 2021 season, because a calculating front office drafted the right guy with the No. 2 overall pick in 2013 and manipulated the service-time system. (The Houston Astros packaged underwhelming pitcher Mark Appel – the first pick that year – in Saturday’s 5-for-2 trade with the Philadelphia Phillies for closer Ken Giles.)  

A team that seemed to have a new manager every year – Lou Piniella, Mike Quade, Dale Sveum and Rick Renteria since 2010 – now has three-time Manager of the Year Joe Maddon. All those sign-and-flip deals for the future ultimately yielded a Cy Young Award winner and multiple key contributors to a 97-win team. 

Now add Heyward, who clearly fits Epstein’s vision of a well-rounded athlete, someone who can grind out at-bats, run the bases, play Gold Glove defense in the outfield and look good on the actuarial tables at the age of 26.   

“The season that we had as a team was something that not many people expected,” Arrieta said after the Cy Young announcement. “Most of those people were outside of our organization, people that didn’t necessarily know everything that we were about, and the types of guys we had, and the character we had overall.  

“To have the pieces that we have aligned for next season – and (a) number of years to come – it looks like we’re going to have a pretty bright future.”     

Cubs Talk Podcast: Mailbag edition


Cubs Talk Podcast: Mailbag edition

3:00 - Listener question: Espada or Ross? Kelly Crull shares some inside info on Joe Espada

7:30 - Kelly talks about David Ross' second interview for the Cubs managerial job.

11:30 - Listener question: Say it is Espada, do you see any way David Ross comes on as a coach behind Espada?

13:30 - Listener question: Could the team regress further due to a lack of familiarity with a new manager?

20:10 - Listener question: How hard will Theo and Jed go after Gerrit Cole? And if he's not available who else is?

23:30 - Listener question: Are you trying to extend Castellanos?

26:00 - Listener question: If you sign Castellanos are you also trading Kyle Schwarber?

28:45 - Listener question: Should the Cubs trade Kris Bryant? What would they get back in return?

33:00 - Lighting round: Will Nico Hoerner be the opening day second baseman and keep the job in 2020?

33:10 - Lightning round: Will the Cubs bring back Cole Hamels?

33:45 - Can we and should we clone Javy Baez so we have a fresh Javy when he retires, or is that unethical?

Listen to the full podcast here or via the embedded player below:


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Cubs reportedly had second interview with David Ross

Cubs reportedly had second interview with David Ross

The Cubs' managerial search is in full swing as they continue to line up intriguing candidates to replace Joe Maddon. In recent weeks, Houston Astros bench coach Joe Espada's name has been floated out as a strong candidate, with reports stating that the Cubs had already scheduled their second interview with the much sought after coach

While the fact that Espada is such a strong candidate in the midst of a World Series run has led many to believe he is the runaway favorite right now, it is still very much so a wide-open race. 

It was reported that while not extremely publicized, former Cub David Ross is believed to have had his second interview with the Cubs organization this week. 

Ross, who was extremely clutch in the Cubs 2016 World Series win, has an obvious and extended history with the organization. And while there are no concrete reports on the nature of any follow-up discussions between Ross and the Cubs, it was stated that the two sides have in fact at least had those expanded conversations.

As Kelly Crull hinted at in her tweet, Ross's position with the franchise definitely makes his negotiations about the managerial opening a bit more fluid, which may lead to fewer updates on his specific discussions with the team.  

Ross and Espada certainly sound like the favorites to land the Cubs' managerial opening, as our own David Kaplan stated that manager Joe Girardi, who has been connected to the Cubs throughout this search, looks like the front-runner for the Philadephia Phillies managerial spot. 

The 2019 World Series between the Washington Nationals and Houston Astros kicks off on Tuesday night. Traditionally you do not see MLB franchises make their managerial hiring announcements during the World Series,  so the Cubs' announcement could come on one of the World Series off-days, as early as Thursday. 

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