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2019 Trade Deadline: Off-the-wall White Sox trade proposals

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Or: Imagine if Jerry Dipoto was the GM on the South Side ...

MLB: Boston Red Sox at Seattle Mariners
High stakes: Jerry Dipoto is easily the most free-wheeling GM in baseball. What kinds of trades would he muster on the South Side if he were in Rick Hahn’s shoes?
Joe Nicholson-USA TODAY Sports

In anticipation of next Wednesday’s trade deadline, South Side Sox has two takes on what the Chicago White Sox should do. First, WSM presents a bit of a fantasy stab at what sort of reshuffling might occur on the South Side if an aggressive GM like Seattle’s Jerry Dipoto — or, in a White Sox context, Frank Lane — was in charge. Later today, Darren Jackson examines the chips the White Sox have in their arsenal, with specific respect to team control — who makes sense to swap away, if anyone?


Jerry Dipoto, currently the Mariners GM, has quite the reputation as someone who never met a trade he didn’t like. Unfortunately for the Mariners, that hasn’t gained his team a playoff entry since 2001, although Dipoto is not entirely responsible for that drought — he’s been only with the Mariners since 2015.

There’s bound to be a deluge of trading activity for the next week, as no major deal been transacted. Below is a small list of off-the-wall trade ideas that Dipoto could potentially swing if he were in Rick Hahn’s role. Many fans understandably won’t like these deals, but they would be creative ways to bring short- and long-term impact for the White Sox, as the team’s playoff window appears to be rapidly approaching.


James McCann, Alex Colome and Aaron Bummer to the Houston Astros for Kyle Tucker, Corbin Martin, Francis Martes and Rogelio Armenteros

The injuries and general inconsistencies, particularly for many the top prospects in Birmingham and Charlotte this year, make it difficult for the Sox to offer prospects packages for more higher-end players. This leaves three options for the Sox GM if he wishes to pursue a trade: Trade current major leaguers, deal quantity over quality (and hope the other team accepts), or perhaps accept a salary dump. This deal is clearly the first option.

Why the White Sox would do it: Kyle Tucker has long been a prized prospect, and he’s currently ranked 10th among all prospects by MLB Pipeline. The 6´4´´, 190-pound lefty outfielder is built like Ted Williams and, while obviously not the Splendid Splinter, is considered a well-rounded prospect. MLB Pipeline grades him 60 for hit and power, 55 for arm, and 50 for field and running. There are essentially no lefty power bats who can play right field who will be available in the upcoming free agent class, so the best way the Sox can fill this need is via trade.

A trade acquisition was considered with the Colorado Rockies for Charlie Blackmon, but due to concerning issues (defense, home-away splits, salary, declining speed), Blackmon may not be the best option. The Sox may be willing to overpay to achieve such a talent as Tucker’s. While the other guys coming to the White Sox have some prospect cred, two of these guys won’t pitch much (if at all) in 2020 and the other, Armenteros, is more of a back-of-the rotation guy who’s ranked 20th on Houston’s MLB Pipeline list, and is currently on the Astros roster as a low-leverage reliever. He’s likely to have a swingman role in the future due to his decent but unexceptional stuff. Martes may be the most controversial of these new pickups, as he’s on the restricted list due to an 80-game drug suspension; unfortunately, he’s yet to serve any of that time due to Tommy John surgery last August. Martes was the 17th-ranked MLB prospect prior to the 2017 season, so clearly the Sox would be buying very low here. The same would apply for Corbin Martin, who underwent Tommy John surgery this month and likely won’t return until 2021; at this moment, he’s ranked 47th in MLB Pipeline’s list.

Certainly this wouldn’t be an easy deal for the Sox to pull a trigger on. The team will have to receive future contributions from Jace Fry, Caleb Frare, Hunter Schryver and other southpaw relievers going forward. Losing McCann would hurt due to the bond he’s had with his Sox pitchers. However, they’ve already received far more than originally expected from McCann, and there is a tremendous free agent catcher 90 miles north of Chicago, Yasmani Grandal, who could be available in 2020. The Sox could still acquire veteran bullpen depth via trade or free agency, which would minimize the loss of Colomé, who’s been excellent this year. Finally, what’s not to like about the potential of an outfield consisting of Jimenez, Robert and Tucker?

Why the Astros would do it: The Astros certainly seem primed for another World Series run, but their two biggest weaknesses are at catcher and left-handed relief. Their catchers: they are combining to hit .219, with as many homers as McCann alone. McCann’s enjoyed a great working relationship with Justin Verlander over the years, and this seems like a natural fit; McCann’s easily the best catcher who could be available via trade. The need for a southpaw reliever for the Astros has been well-documented, and Bummer has been outstanding this season. Finally, Colomé can do nothing but bolster Houston’s already-solid bullpen, while also preventing other teams from acquiring him; while Colomé’s stats are ripe for regression, he still has been rock-solid with 21-of-22 in save conversions and is also quite experienced in a setup role. Bummer’s still under control for several more years, while Colomé and McCann are both eligible for arbitration for 2020. Thus, this trio of players are not rentals, unlike other top available players in the trade market. The Astros lose Tucker in this deal, and they’ve fiercely avoided trading him thus far. However, their outfield depth in both the majors and minors is quite amazing, and can absorb the loss. Plus the team will be adding three significant, controllable players onto the team’s roster. What’s not to like?


Blake Rutherford, Zack Collins, Zach Thompson, Micker Adolfo and Kelvin Herrera to the New York Mets for Jacob DeGrom, Edwin Diaz and Yoenis Cespedes

The New York Mets are in many ways similar to the White Sox: They’ve made bad signings and trades over the past few years, suffered through injuries to key players, and are often considered the second team of their respective cities. Perhaps this is a deal that could help both squads — it would free money and offer a decent prospect haul for the Mets while giving them greater financial flexibility, and give the Sox a veteran ace as well as a closer that they had lost in the Astros trade above.

Why the White Sox would do it: The White Sox could simply try to sign Gerrit Cole via free agency during the offseason, but based on debacles with Manny Machado and Bryce Harper, do you really think the White Sox would be willing to outbid the New York Yankees to acquire him? I don’t, either. And it’s not even just about the money. The White Sox will never offer a contract of five years or longer for any pitcher, no matter how great or young he is. This will be a bit dicey, because DeGrom still has five years and more than $160 million left on his deal (running through 2024), which means he’d be 36 by the time his contract expires. The Sox would get the veteran ace to lead their staff through their contention years, however, and the only reason DeGrom hasn’t neared a 20-win season is due to a lack of run support. With the White Sox lineup as presently constituted, as well as the Kyle Tucker mentioned above, this shouldn’t be a problem going forward.

Would the White Sox consider Noah Syndergaard or Zach Greinke instead? Certainly they are viable options. However, Syndergaard would likely require more prospect capital due to his much lower salary, which the White Sox may not be willing to do if it means relinquishing one of their top four or five prospects. Greinke will be owed $71.5 million over the next two years, so that would be a more viable option. He’d also require less money long-term than DeGrom, but he’s four years older. Greinke in many ways would be more ideal, especially since the Sox wouldn’t have to acquire any dead salaries, like Cespedes’. The ultimate question would be if the White Sox will indeed be playoff-bound in the next two years with Greinke on the bump.

The White Sox also will receive closer Edwin Diaz, who’s struggled with the Mets this year, but was absolutely dominant with the Mariners last year. A change of scenery might do him good. Diaz becomes a necessity in this deal, as few of the AAA-ish guys (Thompson, Zack Burdi, Carson Fulmer) White Sox rookies (Ian Hamilton, Jose Ruiz, Ryan Burr) have looked particularly sharp due to inconsistencies and/or injuries. Diaz will be undergoing arbitration this year for the first time, so because of this, the Sox would have to relinquish more prospects because of his relatively low salary.

Finally, in order for the Mets to pull the trigger on the deal, they’d want to rid themselves of the remaining one year and $29.5 million year remaining on Yoenis Cespedes’ contract. Trading Herrera to the Mets will only offset a small portion of that amount, so the Sox would end up paying a net of $20 million for Cespedes, who may not even step foot on a field next year due to injuries. That’s a lot of money to spend, but if DeGrom and Diaz are on top of their game, it might be worth the risk.

Why do the deal now instead of during the Winter Meetings? Most contending teams are currently looking for rentals in order to minimize potential loss of top prospects. More teams will be looking at longer-term deals during the Winter Meetings, and guys like DeGrom would be higher in demand. Thus, the Sox will have much better chances for success if they attempt a deal now.

Why the Mets would do it: The Mets are in a similar state now as the Sox were prior to the Chris Sale and Adam Eaton deals. The team has plentiful top-end talent, underperforming results, little in the way of high-end prospects, and a team in the state of turmoil. This is a chance for the Mets to regroup. They will be unable to garner the elite prospects the White Sox received in those two aforementioned trades, or even the deal with the Cubs several months later for Eloy Jiménez, because the players the White Sox dealt where in team-friendly deals. DeGrom is due a boatload of money beginning next year, so the Mets wouldn’t get as much in the way of prospect capital if they dealt DeGrom alone. Diaz is thrown into the deal for that reason, as they would receive two or three more prospects than would’ve been received otherwise.

Even with accepting Herrera’s contract, New York would save $20 million in 2020 by unloading Cespedes’ contract to the White Sox — not to mention the remaining $160.5 million and five years for DeGrom (there’s a club option for $32.5 million in 2024). In addition to Herrera, who’s more or less a throwaway, the Mets would receive former first round picks Blake Rutherford and Zack Collins, power-hitting outfielder Micker Adolfo (who should be ready to mash next year), and potential closer Zach Thompson (who’s actually pitched quite well recently at hitting-friendly Charlotte). The extra money the Mets would save could be spent toward acquiring an overall deeper and stronger team going forward.


Jose Abreu and Leury Garcia to the Tampa Bay Rays for Shane McClanahan and Joe Ryan

Jose Abreu, as everyone knows, will be a free agent at the end of the year, while Leury Garcia will be eligible for arbitration. Few contending teams are in real need of a DH/first baseman — Boston, Washington and Tampa Bay are the only ones right now that seem viable. Of those teams, Tampa Bay has easily the deepest prospect pool from which to choose from. As for Garcia, he really won’t cost that much in arbitration. However, due to the currently deep pool of fourth outfielders the White Sox have, he may be available if the price is right. In this case, because the Rays outfield has undergone a recent run of outfield injuries, Garcia would be the ideal player to fill that gap. With both players, they could actually receive more higher-value prospects than they likely would individually.

Why the White Sox would do it: The White Sox have every intention of bringing Abreu back as their first baseman/DH for the next one or two years. However, the team isn’t in contention for a playoff run this year so, if they could rent him out for a couple months and increase the team’s list of prospects, why not? By himself, as a one-dimensional rental, Abreu really wouldn’t be expected to garner a Top 100 MLB prospect. There’s no way the Rays would make him a qualifying offer, so the White Sox would likely have the opportunity to re-sign Abreu in the offseason to a one- or two-year deal.

García has been an exceptional player in 2019, but he becomes a fourth outfielder in 2020 if the Sox acquire a right fielder either during the deadline or upcoming Winter Meetings. With this deal, they’d acquire the 11th (McClanahan) and 16th (Ryan) ranked Rays in what is arguably the deepest system in baseball. McClanahan’s a 22-year-old, hard-throwing southpaw who many have compared to Chris Sale. He is currently pitching in High-A ball, posting a miniscule 0.94 ERA and fanning 40 batters while walking just seven in 38 13 innings. While Ryan doesn’t have the elite stuff that McClanahan has, he definitely knows how to pitch and has fanned 134 while walking just 22 in 91 13 innings this year for the Rays A+ and A squads. Both could be ready to pitch in the majors as early as 2021.

Why the Rays would do it: The Rays would get that much-needed jolt in the lineup that they’ve been missing. The team is in a desperate wild card fight with several teams, and while Ji-Man Choi is a nice player, he certainly isn’t close to Abreu’s level in the power department. With outfield injuries taking their toll in Tampa, García would be the perfect fit for the Rays. He’s a good hitter with above-average speed and a plus throwing arm, and can play anywhere except the battery positions. García can more than cover for any additional injuries the Rays may suffer through, and he’s a solid switch-hitter to boot. García is also under team control through 2020. For most other teams, McClanahan and Ryan would easily be Top 10 prospects. However, because the Rays system is so deep, they could lose both players and hardly miss a beat.


In the one-in-10 billion chance all three above trades occur, the White Sox would set themselves up for a significant run in 2020. The team could have a combination of Jiménez-Robert-Tucker in the outfield, Moncada-Anderson-Madrigal-Abreu in the infield, and Zavala at catcher (with the opportunity to acquire a free agent backstop in the offseason). The starting rotation would look good, provided everyone’s on top of their game: DeGrom, Giolito, Kopech, Cease and Lopez, with Rodón as the wild card when he returns midseason. The bullpen would be on shaky ground, but that’s always one of the easier spots to fill in over the offseason.

I tried not to cherry-pick and do something laughable, like a Cubs fan suggesting on MLB Trade Rumors less than a week ago that Kansas City swap Chicago Whit Merrifield and Ian Kennedy for Addison Russell and Kyle Schwarber. If anything, the deals above may end up being in the opponents’ favor — especially the first two.

I looked primarily at acquiring talent that’s relatively close to major-league ready. Would Dipoto do these deals? I don’t really know. In many ways, I’d hate to lose the likes of controllable players like Bummer, McCann, Colomé and García — even though the last three are controllable for just one more season. It’d also be difficult to surrender prospects like Rutherford, Collins and Adolfo, and it’d also be excruciating to pay so much moolah on somebody who might not end up playing, like Cespedes.

The question is: would the White Sox be better positioned to win both in the short- and long-terms with DeGrom, Diaz, Tucker, McClanahan and Ryan, knowing that additional free agents (Grandal, anyone?) could be available to bolster the team further?