Cubs May Need to Examine Front Office While Determining Future of Managerial Position

As an injury-plagued Cubs team stumbles towards the end of the regular season, and their probability of regaining the Central Division crown and winning another World Series championship steadily decreases (16.4% and 2.7%, respectively, according to FanGraphs as of September 9), many have begun looking forward to the end of the Joe Maddon era on the North Side.

The Cubs immediately winning a championship during the expected window of contention gave rise to expectations of being perennial title contenders, understandably so. However, they were clearly overmatched in the 2017 NLCS and fell apart late in 2018 as they were caught by the Brewers and subsequently shut out in both Game 163 and the NL Wild Card.

While the manager is generally the first to take the blame, the underlying issues behind the Cubs’ underperformance raise questions about the future of the front office. It’s somewhat unusual to keep a group of executives together as long as the Cubs have, with Theo Epstein, Jed Hoyer, and Jason McLeod all serving together since 2012, and their continued partnership is far from assured.

The latter two have been connected to or even interviewed for other positions in the past, and now there’s a spot open in Boston. We’ve seen other defections from the front office ranks in the past, not all of which were simply matters of seeking greener pastures, but no unrest has really reached the upper echelons. Yet.

The main issue in 2019 has been lack of depth on a roster that hasn’t played up to expectations, something Epstein has admitted publicly. While the front office was hamstrung in the offseason by an unexpectedly tightened budget, the farm system was also depleted from prior trades made to bolster the team in prior years. That has left the Cubs unable to go after some of the top pitching options on the trade market or to call up capable reinforcements.

Meanwhile, teams like the Astros and Yankees have had the depth to cover for injured players and still remain comfortably atop their division standings. How much responsibility will Cubs ownership place on Epstein for these issues? While Maddon has produced some head-scratching lineups and made questionable bullpen decisions, he is not responsible for building the roster and is limited to the tools given to him by Epstein. If Maddon does not deserve another contract, the Cubs should also examine Epstein’s stewardship of the team.

But even if Maddon is the only major departure this winter, uncertainty surrounding the continuity of organizational leadership may have bearing on the Cubs’ search for a replacement. Near the end of the 2016 season Epstein and his top lieutenants signed five-year contract extensions that run through the 2021 season. That means a new manager is only guaranteed two years with the front office that hired him, after which the potential for a new regime could bring sweeping changes.

A fickle position under the best circumstances, being the skipper brought in to succeed the man who brought the Cubs their first title in over a century adds a great deal more pressure. And that’s before you consider a team in flux after disappointing results and the uncertain future of execs and star players alike.

As such, the Cubs may have to decide whether or not to extend Epstein before interviewing managerial candidates. This could also depend on whether they are looking for an experienced replacement or an untested individual. An experienced MLB manager is more likely to require additional security in a new gig, while a first-timer may simply be more grateful for an opportunity to manage in the big leagues and therefore less demanding.

The trend around MLB has been to hire younger managers with little to no coaching or managerial experience to take over open positions. Aaron Boone previously worked in the Sunday Night Baseball television booth before taking over the Yankees in 2018. Rocco Baldelli of the Twins and Charlie Montoyo of the Blue Jays both launched their MLB management careers this year.

I fully expect the Cubs to be interested in an untested candidate, in because ownership seems to be increasingly budget-conscious. A younger manager is, after all, a cheaper manager. Alex Cora of the Red Sox was one of the lowest-paid managers in MLB prior to a dominant 2018 season and World Series win that resulted in a contract extension and pay raise. An inexperienced skipper is also much more likely to be a direct extension of the front office, something the Cubs might be looking for in a departure from Maddon’s more headstrong style.

Fans should appreciate the roles Maddon and Epstein played in leading the Cubs into a new era and ending the 108-year title drought. After failing to run it back, however, it appears the franchise has reached what Pat Hughes would call a turning point. The Cubs can either maintain the status quo or put faith in the front office to make changes to team leadership. Or they could clean house on the baseball side.

It will also be interesting to see whether ownership pulls out all the stops to continue fielding a winner. That could be a major determinate for the direction of the franchise and the makeup of the group steering the ship.