Cubs Opinion

Cubs’ Front Office Savvy will be Tested at Deadline

The Trade Deadline is almost upon us, and it's becoming increasingly clear the Cubs won't make a big splash. Savvy, calculated moves are still available, however, and just might help this team make a deep playoff push.

A report by Jesse Rogers last Wednesday detailed an obvious truth for a shaky Cubs team as the trade deadline nears: the Cubs will be casting a “wide net” for roster upgrades before 4pm tomorrow. While on its face this is understandable given the still opaque market, it’s also a bit maddening for fans of the North Side squad.

This is a front office that went all-in on this championship window the past couple of seasons. Acquiring Jose Quintana for two elite prospects well ahead of the 2017 deadline then shelling out significant money to further bolster the rotation prior to the 2018 season proved as much. They were unafraid to make bold — perhaps even desperate? — moves in order to maintain this window of contention while the core of position players remains in tact. And given the frustrations of last off-season (whether we’re speaking of the shadiness of the Ricketts family, Addison Russell‘s continued employment, or the fact that the front office was hand-cuffed from spending more money) it’s not at all surprising that this team is struggling to tread water, clinging to a first place tie with the Cardinals in the chaotic NL Central.

These frustrations run deeper, however, given Theo Epstein’s admission that the 2019 iteration of this team should be judged by production over potential. That assertion rings hollow at a time when Russell had a roster spot until last week despite his lackadaisical and sub-par play, that Albert Almora necessarily receives significant playing time despite being one of the least productive hitters in the league, and Daniel Descalso maintaining his roster spot until he hit the IL, receiving just seven at-bats in the month of July.

While casting a wide net is necessary, particularly with all of deadline’s confusion this season, it’s going to take a succession of savvy deals to plug all of the roster’s leaks. For the Cubs to feel confident — both during the pennant race and into October — the front office needs to find significant reinforcements by tomorrow. This applies to the bench and the bullpen.

Fortunately for the front office there is a surplus of available talent, at least if rumors are your thing.

The Bench Can Improve Without a Blockbuster Move

To be perfectly fair this front office is not in an enviable position. Sustaining a championship window for this long creates difficulties, and that is now quite clear as the team faces Luxury Tax constraints and a farm system that lacks both depth and high-end talent. Departing with any of the few high-upside plays they do have (Nico HoernerAdbert AlzolayMiguel Amaya) would require a pipe dream of a return in Whit Merrifield that’ll never happen. And, clearly, they aren’t giving up any of their limited prospect capital for a reserve player or a rental reliever.

Although it remains to be seen if any trade is made for a bench piece, internal options leave plenty of intrigue. Ian Happ‘s return to the bigs last Friday reloaded the team with versatility, even if he’s yet to perform at the plate. Ben Zobrist‘s imminent return furthers the bench’s depth and versatility, meaning Victor Caratini or Martin Maldonado might very well be dealt for relief help as the oddity of carrying three catchers on the roster probably won’t last much longer.

In the bargain bin world, Tony Kemp was designated by Houston, and while he’s struggled in 2019 he offers a skill set that should intrigue the Cubs. (Indeed, rumors have tied him to Chicago). His production isn’t at all eye popping but he’s still managed to be a roughly league average bat (wRC+ of 96) with hidden power, some speed, and excellent contact skills (15.6 K percentage). He also provides defensive versatility and hits from the left side, but has zero experience in the majors at shortstop — and the Cubs are in dire need for an emergency backup to Javier Baez.

The Cubs have also been linked to Jarrod Dyson, a trade target I touched on a few weeks back, and with regard to that wide net the front office is casting his name has been frequently linked to the Cubs of late. His fit is a logical one as he plays excellent outfield defense and can hit righties at a passable clip. He also has tremendous speed (24 steals this season) and above average contact skills (18.6 K percentage) on an affordable contract. In short, he’s the type of player this front office previously sought in the now-defunct August waiver trade period.

While Nicholas Castellanos remains on the Cubs radar, the fit is curious at best given his limited defensive ability, his sizable contract relative to other trade targets, and that the Tigers are likely seeking too steep a cost for his rental services. While his bat (.282/.339/.478, league average strikeout rate) plays anywhere his glove doesn’t, even if he’d be willing to try his hand at multiple positions.

The best fit — aside from Merrifield, of course — would have been Eric Sogard. His contract is eminently affordable and while he’s enjoying a career year (.299/.363/.480, 124 wRC+) his rental status and career track record didn’t cost Tampa Bay much to acquire him. His ability to play all over the field — including serve as Javy’s backup — along with his terrific contact skills (14.2 K percentage), decent power (10 homers), and a dash of speed (six steals) give the Rays what the Cubs desperately needed.

It remains to be seen what move the Cubs make with regard to shoring up the bench, but when the two best pieces are either 1) unlikely to be traded or 2) already acquired from another contender creativity becomes that much more poignant.

Bullpen Help Remains Murky

Awhile back it appeared the Cubs were going to be significant players for Will Smith, an obvious target for a team desperately needing a dominant back-end presence and a lefty. Clearly Smith fits both needs, and while he was once expected to be traded that’s a much less likely reality now that San Francisco is suddenly in the thick of the Wild Card hunt — in Bruce Bochy‘s final season, no less.

The Giants could still dangle some of their veteran relievers — indeed, the Cubs recently picked up Derek Holland — while attempting an honest playoff run, though that seems somewhat far-fetched for a team and fan base that’s been energized to the extent they have. Unfortunately, this more-than-likely means Smith, like Merrifield on the position player side, has become an unrealistic ideal.

A few weeks back I speculated on a few lefties the Cubs could pursue — all of which are affordable and have success against same-handed hitting. It’s not worth spilling much more ink over this list, however (save for adding Roenis Elias from Seattle, who’s likely available) as the reliever market remains mysterious with the deadline ever-so-close. The Cubs are likely still kicking the tires on lefty relievers, Holland’s LOOGY status notwithstanding, even as their righty options remain somewhat uncertain after Craig KimbrelSteve Cishek, and Brandon KintzlerRowan Wick has become all the rage over the past several days, the excitement regarding him understandable given his velocity sits in the mid-to-upper 90’s and his hook is better than average.

The Cubs already got one lefty to compliment Kyle Ryan. And while we still have no clue if the front office has significant traction on other trades, I’d be flat shocked if the bullpen isn’t upgraded by 4pm tomorrow.

A Lack of Fireworks isn’t Necessarily Bad

Regardless of how the trade season ultimately unfolds for the Cubs you can bank on them making ancillary moves over a big splash. Such moves may or may not work out, and this team’s ability to make a deep playoff run is entirely unclear. We could see Theo pull a roster shakeup like he did with Boston in 2004, though it’s highly doubtful such a move would be as storied as that trade, and further unclear if such a roster-altering move would have its intended impact.

In some respects it’s the front office’s fault the Cubs are in this convoluted state. Joe Maddon has performed well, despite his lame-duck status and his oft-questionable pitching maneuverings, and it remains the responsibility of Theo and Jed to give him the right tools to make another championship run. To date the 2019 Cubs are more maddening than impressive, and it’s unclear that the deadline alone can cure what ails this roster.

The trade deadline will pass as the Cubs fight the Cardinals for NL Central supremacy. Hopefully they leave St. Louis in first place, with new pieces to fit their roster puzzle.

Follow Austin Bloomberg on Twitter for more Cubs news and opinion.

(All stats courtesy of Fangraphs unless otherwise noted. All contract info courtesy of Spotrac.)


Austin is the Lead Cubs Writer for The Loop Sports. He's a lifelong baseball junkie (due to his father) and as a former college pitcher has a particular affinity for the art of pitching. Austin loves to commute in Chicago on his bicycle, and enjoys camping and canoeing as often as possible. He attained his master's degree in Social Justice and Community Development from Loyola University Chicago in 2014.

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