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Don’t Stop Now, Boys

by Sox On 35th Contributors

Written by Mark Schackmuth

A Man of His Word

One month to the day after surprising the baseball world and White Sox fans alike with the signing of Yasmani Grandal, Rick Hahn & Co. struck again, agreeing to terms on a three-year deal with southpaw Dallas Keuchel. The $55.5 million deal, which has the potential to grow to four years and $74 million should Keuchel reach 160 innings pitched in years two and three of the contract, represents the first Scott Boras free agent the White Sox have come to terms with of any consequence.

Until the Saturday evening news was delivered by Jeff Passan of ESPN, a great deal of impatience and frustration had been spreading like wildfire through the White Sox fanbase, despite the early strike made in signing Yasmani Grandal. In the month that has passed since the pact with Grandal, the White Sox front office has narrowly missed on Zack Wheeler, acquired Nomar Mazara for Steele Walker, reached a one-year agreement with Gio Gonzalez, and finally, consummated the deal with Keuchel. Despite a lingering concern by a skeptical fanbase, the White Sox have thus far held up their end of the bargain, obligating the franchise to some $180 million this offseason, even if most fans don’t necessarily count bringing back Jose Abreu as a true offseason addition.

A Foundation Set

The obvious question remains, where does the organization go from here? With Grandal, Keuchel, Gonzalez and Mazara in tow, even a critical baseball media and outspoken fanbase would concede this has been a successful offseason for the executives at 35th and Shields. While it appears as though a DH or right-field platoon bat may yet be brought into the fold, Rick Hahn has accomplished what he candidly set out to after baseball drew to a close in 2019.

The starting rotation appears to be stabilized, and the White Sox now have options regarding whether Michael Kopech heads north to Chicago when Spring Training ends, or retreats to Charlotte to further refine his arsenal after returning from Tommy John surgery. Once Kopech does make his triumphant return to Chicago, the White Sox will have options for the utilization of Gio Gonzalez or Reynaldo Lopez, and should Carlos Rodon return midseason, for both of them. As a result, over the past week, the White Sox have turned a glaring weakness into a potential strength, particularly since both Lopez and Rodon also provide intriguing possibilities as high-leverage relievers.

With their rotational issues apparently addressed, the sheer number of ways that Grandal should improve the club, Luis Robert, Nick Madrigal and Kopech on the way, and the right field chasm bridged for now, anyway, the White Sox have the luxury of stepping back and taking a deep breath. They will certainly check in on the relief market despite a number of internal options, but should the White Sox do little else for the remainder of the offseason, the odds are fairly significant that Rick Hahn has a ballclub on his hands with 85-win potential.

While this would certainly be a vast improvement over the previous three seasons, and signal the beginning of what most Palehose fans hope is a sustained run of competitiveness, there remains significant opportunity to achieve more in 2020. The White Sox brass, for all its detractors, and as I have written extensively about previously, has assembled an outstanding core of young talent. Although it might be more encouraging from a long-term standpoint to see more of this core developed more organically, rather than acquired through trades for valuable major league assets, the fact remains that its production on the field is of far more importance than the particular manner in which it was assembled. Ultimately, Rick Hahn will be judged not on the genesis of his young team, but on the basis of whether he is able to leverage it into the end result he has consistently proclaimed – a sustainable, competitive team, capable of winning multiple World Series Championships.

Time to Strike

The current composition of the White Sox roster, for all that it has improved, is still more a vision than a reality. If Rick Hahn truly wants to build an organization that perennially competes for championships, he must not rest on his laurels. Young, cost-controlled talent provides the foundation for all consistently successful organizations, but dependable, proven superstars are what completes the championship puzzle. While several members of the White Sox young core may eventually develop into superstars, today they are still works in progress. What the White Sox still need, particularly after missing on a rare opportunity last offseason, is a proven, premier superstar caliber player in the prime of his career.

And yet, as has been proven in the Wheeler episode, the White Sox are not yet a premier destination for free agents. Nor are the White Sox particularly fond of entering irrational bidding wars for top-tier free agents. As Gerrit Cole, Stephen Strasburg and Anthony Rendon have already signed, it is quite clear such a superstar addition is not happening via free agency this season. Outside of potentially signing their own free agents in the future, it probably is not going out on a limb to say it won’t ever happen under this ownership regime.

Interestingly, this is not as significant of a problem as it might seem at first blush. The real challenge for the Sox’ front office is not necessarily deploying their resources – as the prominent narrative currently stands – but how to do so in such a way that extends their competitive window as far into the future as possible. As mentioned above, irrational bidding wars generally aren’t going to achieve this result, but being opportunistic in the trade market certainly might. The reason: the White Sox can deploy more than just their financial flexibility; unlike in free agency, in a trade, Rick Hahn can leverage the strength of his farm system, and even his young core, if necessary, to entice opposing general managers.

The flexibility the White Sox have built, both in terms of a wealth of both payroll capacity as well as cost-controlled assets, is currently nearly unmatched throughout Major League Baseball. While there are a number of clubs currently rebuilding, that as a result, have significant capacity to absorb payroll, the White Sox are perhaps the only one that is truly transitioning to a competitive state. Moreover, while some clubs have strong prospect capital or young core players to assemble a high quality package to attract a superstar player, few of those same clubs also possess significant ability to absorb a long-term, high-dollar commitment. In summary, the White Sox’ ability to both absorb cash, and move cost-controlled talent in a potential deal for a superstar is stronger than arguably 90% of the League. This makes Rick Hahn and the White Sox an ideal trade partner this offseason.


What does this all mean? What are the opportunities that genuinely exist for the White Sox to add to a trajectory-altering, superstar to their core this offseason? Let’s just lay the cards on the table:

Boston Red Sox – Chaim Bloom and his associates have a mandate to shed enough 2020 payroll to get below the Competitive Balance Tax of $208 million. The Carmines’ current payroll projects to eclipse $229 million, according to Cots Contracts. As a result, Bloom must attempt to fortify the weaknesses that undermined the 2019 roster while shaving some $22 million off the payroll.

Enter, stage right, Rick Hahn, with some $30 – $40 million in potential annual payroll capacity for 2020 and beyond. After the signings of Grandal, Abreu and Keuchel, the White Sox likely have approximately $110 million on the books for 2020. It has been widely speculated that Bloom’s primary subtraction is David Price, who is owed $96 million through 2022. While Price brings with him a pedigree worthy of such an investment, he has been limited to 358 innings over the past three seasons, and enters the 2020 season at 34 years of age. To be frank, Bloom isn’t going to move Price without eating ~ $50 million in cash or sending a player with the potential to bring significant surplus value carrying Price’s bags. Keuchel’s three-year deal evidences where the likely market is on Price, and his primary suitor – the White Sox – just exited the equation. Despite this, thus far, it appears Bloom, likely biding his time while Hyun-Jin Ryu remains on the market, is unwilling to package anyone other than Jackie Bradley Jr. with Price.

This simply will not get a deal done. Rick Hahn was not willing to absorb $96 million for David Price without a player with a much higher ceiling than JBJ coming back. Bloom may ultimately determine that it makes more sense to gamble on keeping Price in the fold, and moving a position player with significant 2020 dollars attached. Potential alternatives likely include Mookie Betts and J.D. Martinez. While Betts is undoubtedly attractive to a number of teams looking to win now, his impending free agency limits his allure, and given the fact that the Red Sox are expecting to compete again in 2020, it makes little sense to move their best ballplayer for anything other than a significant return. This likely leaves Martinez, who, for all his talents, eschewed his opt-out despite clear interest from the White Sox, implying his fondness for Boston and raising concerns that he would opt-out after 2020 in the event he was traded. While Chaim Bloom will solve Boston’s payroll issue one way or the other, I do not anticipate it will be through a trade with the White Sox.

Cleveland Indians – Chris Antonetti and Mike Chernoff are attempting to retool the Indians while in the midst of their competitive window, and sustain their ability to compete in a weak AL Central despite the natural boom-bust cycle of modern professional baseball. Buoyed by their ability to develop young starting pitching, Antonetti understands his ownership will never commit to the mountain of years and dollars Francisco Lindor is certain to command when he hits free agency after the 2021 season. Whether Antonetti and Chernoff are able to negotiate a return for Lindor before February, or wait until the 2020 trade deadline is unknown, but Lindor’s time in Cleveland is waning.

Does it make sense for the White Sox to explore a potential deal for Lindor with the Indians? The obvious constraint here is Tim Anderson, who has held down shortstop on the Southside since 2016 and remains under contract until as late as 2024, assuming the White Sox strike their affordable club options. Additionally, Anderson has arguably become the face of the White Sox franchise as a result of his brash, outspoken support of playing the game in an entertaining fashion. Despite all this, there is a scenario wherein Anderson remains part of the core in the event of a Lindor acquisition by being shifted to the outfield, where his speed and athleticism would undoubtedly be valuable. Perhaps a defensive alignment of Anderson in center, flanked by Robert in right field would offset the defensive limitations of Jimenez.

If one accepts that Lindor is a potential fit – and given his prodigious talents at shortstop he would be a vast improvement for all but a few teams – the question then becomes what would it take to convince Antonetti to move the talented superstar to a divisional up-and-coming rival? The answer: a LOT. Likely more than the White Sox would be willing to part with given the price Lindor will require in free agency. Perhaps a deal based on Andrew Vaughn, Nick Madrigal and Zack Collins could entice the Indians, but it simply creates too many holes for the White Sox given Lindor’s near-certain departure after 2021. Should Antonetti hold onto Lindor to reassess his options at the trade deadline, perhaps the clubs revisit the possibility, with the benefit of a more firm outlook on 2020.

Colorado Rockies – Jeff Bridich is staring at a $150 million payroll for 2020 with insignificant odds to compete for the National League West title. Bridrich is in a position not so dissimilar from the one Rick Hahn and Ken Williams found themselves in 2016: a very talented core, with a lack of organizational depth. Featuring superstar Nolan Arenado, a talented shortstop in Trevor Story, organizational stalwart Charlie Blackmon, as well as a number of reasonably intriguing young players. The Rockies are facing a bit of a moment of truth – do they 1) proceed down the path outlined prior to 2019, when they extended Charlie Blackmon and Nolan Arenado, fortified a bullpen with Bryan Shaw and Wade Davis, and sought to rely upon young foundation of Trevor Story, Brendan Rodgers and Ryan McMahon, or 2) attempt to clear the payroll committed to Arenado and/or Blackmon to redeploy in the future to realign with their starting pitching and other young core pieces that have struggled through injury and consistency issues?

What is clear is that Bridrich is at least willing to consider the latter, with rumors that the Rockies are listening on Arenado, with the Texas Rangers – having missed out on Anthony Rendon – being the most publicly mentioned potential suitor. The challenge with Arenado is that despite his superstar production, and a competitive disposition and temperament teams are fond of, the Rockies paid him handsomely last offseason. With seven years and $234 million remaining on his contract, even if Arenado does adjust to life outside of Coors Field and produce similarly playing 81 home games at a lower elevation, he is unlikely to provide significant surplus value. His annual average salary of approximately $33.5 million equates to between five and six Wins Above Replacement. Over the course of the past 5 years, the superstar third baseman has produced right about five-and-a-half Wins Above Replacement per season. What this ultimately means is that while the dollars deployed to Arenado are productive, they simply aren’t incredibly efficient. And their efficiency will likely decline as Arenado enters the final years of his contract.

And yet, the efficient deployment of resources doesn’t win World Series Championships. Superstar ballplayers win World Series Championships. Perhaps more importantly, the ability to effectively absorb the premium salaries of premium ballplayers necessary to win championships is precisely the desired outcome of rebuilding teams. I don’t truly believe any Major League Baseball organization seeks to prove they can win titles with the lowest possible payroll. Instead, they seek to assemble the most talented roster within their provided payroll constraints. Superstar players such as Arenado are obligatory components of every championship ballclub.

Additionally, one must assume Bridrich isn’t going to part with the face of his franchise without a potential star coming back in return. Despite the benefits of shedding some $200+ million in financial obligations, the Rockies’ GM isn’t surviving the jettisoning of a superstar he just extended last year through extolling the virtues of the financial flexibility Arenado’s expulsion creates. Bottom line: Bridrich must bring back a player that Rockies fans can celebrate for years to come.

The Deal

As mentioned above, any White Sox acquisition of Nolan Arenado, despite the lack of surplus value the third baseman will provide, will require a premium young talent heading back to the Rockies. The White Sox would likely push Andrew Vaughn as a potential centerpiece, regaling Colorado on the idea of Vaughn destroying baseballs in Coors Field in such a way that might assuage the disappointment Rockies fans would have from seeing Arenado traded away. Ultimately, however, Bridrich will want a player he can pencil immediately into his 26-man roster in 2020, which Vaughn is not. While Nick Madrigal makes some sense from the White Sox perspective, as adding Arenado would allow the White Sox to shift Yoan Moncada back to second base, Madrigal’s ceiling may be lower than the Rockies would consider as a centerpiece.

Enter, stage left, Dylan Cease. Rick Hahn would undoubtedly struggle mightily with the idea of moving Cease so early in his White Sox tenure, but the stuff Cease possesses is ultimately what convinces Major League general managers to take significant risks. The White Sox were willing to take one with Zack Wheeler, the Yankees obviously took a significant one with Gerrit Cole, and making Cease available is what it might take to convince Jeff Bridrich to move perhaps the most productive and popular player the Rockies franchise has ever known.

Removing Cease from the White Sox rotation obviously stings, but with the emergence of Lucas Giolito, the imminent return of Michael Kopech, and the potential of Reynaldo Lopez and Carlos Rodon still in the fold, albeit not without a fair share of frustration, the White Sox rotation is not facing any deficiencies when it comes to frontline stuff. Moreover, despite the vast potential in Cease’s right arm, there exists at least as great a chance that Cease never reaches that potential, in a White Sox uniform or otherwise. Given the stellar, proven performance Arenado has amassed over the course of his career, there is a reasonable argument to be made that parting with Cease, while his shine remains significantly bright, makes sense for the White Sox.

The second piece is likely where a potential Arenado for Cease deal bogs down. Bridrich will push for Andrew Vaughn, while Hahn will counter with a lesser piece such as Zack Collins or a member of a once-promising but slow-developing outfield contingent. Assuming the White Sox are willing to accept most of Arenado’s salary – and they should be – Rick Hahn would likely have the upper hand when negotiating this part of the deal. It simply is unlikely that the Rockies will do better than a scenario wherein they receive an arm with as much potential upside as Cease, offload most of Arenado’s money, and receive significant secondary pieces. A package of Cease, Zack Collins and Blake Rutherford or Luis Alexander Basabe for Arenado and $20-25 million might be difficult for both GMs to walk away from. The fit is simply too good.

Such a roster construction drastically improves the ballclub from both an offensive and defensive perspective, while removing pressure on a youthful starting rotation, two members of which are returning from significant injury. Offensively, the White Sox would feature one of the most dynamic offenses in all of baseball, featuring an unrivaled power and speed combination. Defensively, shifting Moncada to right field, paired with Luis Robert shortly in center, provides outstanding athleticism in the outfield, offsetting Jimenez’ athletic limitations in left field. Arenado is defensively elite at third base, as is Madrigal at second base.

There is no disputing that the subtraction of Dylan Cease from the rotation would hurt. And yet, with Keuchel and Gonzalez in the fold, and Lopez’s durability a known commodity, the loss of Cease may not be as harmful as expected. Carlos Rodon, who seems to have largely been written off by many, could return by midseason and ease Cease’s departure.

Rick Hahn & Co. have assembled a diverse, dynamic young core. The additions of Yasmani Grandal and Dallas Keuchel have supplemented that core, with Gio Gonzalez and Nomar Mazara providing necessary depth and flexibility. The following, White Sox fans, is a playoff-caliber roster for years to come:

  1. Luis Robert – CF
  2. Yoan Moncada – RF
  3. Nolan Arenado – 3B
  4. Jose Abreu – 1B
  5. Eloy Jimenez – LF
  6. Yasmani Grandal – C
  7. Tim Anderson – SS
  8. Nomar Mazara/James McCann – DH
  9. Nick Madrigal – 2B
  • SP 1 – Lucas Giolito
  • SP 2 – Dallas Keuchel
  • SP 3 – Michael Kopech
  • SP 4 – Reynaldo Lopez/Carlos Rodon
  • SP 5 – Gio Gonzalez

Rick Hahn & Co., don’t stop now, boys.

Follow Mark Schackmuth on Twitter @iamshack24.

Featured Photo: Colorado Rockies/Twitter

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