What the trade deadline looks like when your team is bad, your owner is cheap, and your farm system is barren

Unless they either seriously crush or blow the next 10 games or so, the frustrating reality about the White Sox is that come the end of July, there will still be a feasible enough chance at winning the AL Central to justify making trades.

Historically, White Sox trade deadlines have been frustrating affairs, even when in contention. I’ve already covered Rick Hahn’s generally brutal trade history in these pages, but it goes even farther back than his tenure: The 2009 acquisition of Jake Peavy stands as the only true deadline splash made by this team in-between last year’s Craig Kimbrel trade and the humorous acquisition of Jurassic Carl Everett in back-to-back seasons of 2003-04. (I’m only counting players that the team indisputably wanted and meant to acquire, so there will be no Alex Ríos talk in here.)

Given that history and the circumstances presented by this season, the names I’m about to throw out here probably aren’t the ones you want to hear. The Sox are in a difficult situation, of their own making. As long as the AL Central is within sight, there’s little justification to not at least attempt to get better and give themselves a shot at the playoffs in a supposed “championship window” year. Simultaneously, it’s also true that the likelihood of this team winning the World Series is low enough that it’s simply not worth skimming from the top of an already-barren farm system in a desperate attempt to make a major splash.

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Among those who still have an optimistic view of the South Side chances, the 2021 Atlanta Braves are a popular point of reference to demonstrate that all is not yet lost. At the same time, the 2021 Braves were a team that decided to actively try to get better once they lost their star player to injury and it was clear that their best-laid preseason plans weren’t working, which seems a philosophy entirely foreign to this White Sox organization. It was almost exactly a year ago to the day that the Cubs announced their rebuild by trading Joc Pederson to Atlanta, and within several weeks, Jorge Soler, Adam Duvall, and Eddie Rosario were in Braves uniforms and well on their way to becoming postseason heroes.

None of those players were performing particularly well at the time of their trade, but following Ronald Acuña’s injury and Marcell Ozuna’s domestic violence suspension, Atlanta was consistently starting outfields that included Guillermo Heredia, Abraham Almonte, and Ender Inciarte. GM Alex Anthopolous knew that this was untenable, and so he made moves, even if there was no guarantee that they’d work out. To have a shot at competing this season, it’s absolutely imperative that Hahn take the same approach.

Joc Pederson had a 90 OPS+ when he was traded for Bryce Ball, who is now the Cubs’ 32nd-ranked prospect according to FanGraphs. Despite being 20 months removed from leading the league in home runs, Jorge Soler and his 78 OPS+ were sent to Atlanta for a minor league reliever currently ranked 39th on Kansas City’s prospect list. Adam Duvall drove in 45 runs in 55 games as a member of the Braves after being acquired for Alex Jackson, a 25-year old former sixth overall pick who’s struck out in more than 50% of his career MLB plate appearances.

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Those are the types of moves the Sox will most likely need to make to have a prayer at doing anything worth doing in 2022. Lenyn Sosa or Colson Montgomery won’t be enough to bring Luis Castillo or Ian Happ to Chicago. Being unwilling to use them in a trade for someone in the David Peralta or Brandon Drury tier of deadline mercenaries isn’t overvaluing prospects; it’s admitting that the sustained winner fans were promised is contingent on players like Sosa and Montgomery being productive players for the White Sox, rather than for someone else as mid-tier trade bait.

With all that being said here’s a jumble of candidates who I, a person with no inside sources or connections whatsoever, think might fit the bill. They may be just as unrealistic as you think they are — again, I’m the wrong person if you want an inside look — but the pickings are slim for a team that’s spent the past several decades sniffing around other teams’ scrap heap.

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Tyler Naquin

.255 AVG ⚾️ .778 OPS (107 OPS+) ⚾️ 6 HR ⚾️ 23 RBI ⚾️ 6.8% BB ⚾️ 26.4% SO

An impending free agent for whom Cincinnati shouldn’t require a hefty haul, Naquin is a familiar face from his days with the now-Guardians from 2016-20. Though he still can’t do much damage against lefties, Naquin has quietly been a quality platoon righty-masher more often than not during his big-league career. He’s running a 106 OPS+ for the Reds this year after posting a 105 mark in a career-high 454 plate appearances in 2021, mostly against righties. The uneven (mostly bad) performance of AJ Pollock and Gavin Sheets means that a viable lefty corner bat is as much of a need as it was six months ago, and Naquin is nothing if not ... viable. The most I can do to talk you into Naquin is that he’s capable of getting hot enough to do serious damage for a few weeks at a time, and sometimes that’s all it takes.

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Dominic Smith

.219 AVG ⚾️ .619 OPS (77 OPS+) ⚾️ 0 HR ⚾️ 17 RBI ⚾️ 7% BB ⚾️ 23% SO

Smith’s OPS+ of 78 so far in 50 games this year following an 83 mark last season means he’s running out of rope with the Mets, who like the White Sox have a glut of first base/corner outfield options that needs to be culled sooner or later. The difference is that most of the Mets options are actually good. An immensely powerful left-handed bat capable of playing the corner outfield — capable being the key word — Smith is essentially a higher-upside carbon copy of Sheets, but with a track record of being able to hit for more than a few weeks at a time. If the latter continues to underperform (recent hot streak aside), I see no issue with taking a flier on a hitter who looked flat-out dominant at times in 2019 and 2020, particularly one that’s walking more and striking out less than most Sox hitters even in the midst of such massive struggles.

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Robbie Grossman

.207 AVG ⚾️ .598 OPS (75 OPS+) ⚾️ 2 HR ⚾️ 19 RBI ⚾️ 12% BB ⚾️ 30.1% SO

It feels unlikely that the Tigers would deal within the division — they rarely have, in recent memory — but if they’d entertain the possibility, I’d be calling about Robbie Grossman. The switch-hitting outfielder is playing this season on a one-year, $5 million contract but has followed the last two seasons of solidly above-average production (117 OPS+ in 207 games) with a .207/.314/.286 line that makes him of little use to a Tigers team that’s at the very least likely to be completely out of the playoff picture before the White Sox.

If there’s a theme among these five hitters, it’s that they typically strike out and walk at league-average rates, if not this year, then over the course of their careers. Grossman’s career strikeout rate is nearly 10% less than than his 2022 mark, and he’s still drawing walks at an excellent clip. Until this year, he rivaled Juan Soto in terms of how difficult it was to get him to chase pitches outside the zone. A healthy and rejuvenated Grossman brings the exact skill set that the White Sox desperately lack. Whether he has the ability to bounce back — and where Detroit’s willingness to trade winds up — remains to be seen.

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Joey Wendle

.287 AVG ⚾️ .761 OPS (115 OPS+) ⚾️ 2 HR ⚾️ 13 RBI ⚾️ 7.6% BB ⚾️ 9.2% SO

Wendle doesn’t fit the bill of underperformer, as he’s playing at least 10% better than average on offense for the fourth straight season and fifth out of six in the majors. His general lack of power has limited his trade value in the past — the outfielder Miami sent to Tampa Bay to acquire him is hitting .197 in Double-A — to the point that he almost certainly wouldn’t cost much of a ransom, should a fading and perpetually-selling Miami decide to make him available.

Blessed with the ability to play both the infield and corner outfield, Wendle would essentially replicate Leury García with an infinitely more palatable (if perhaps not timely!) bat. Wendle has a $6.5 million mutual option for 2023 on his contract, to which he probably won’t be inclined to opt in if he continues his production through the end of this year. Miami likely has at least some designs on contending next year, there’s a non-zero chance that Wendle plays well enough to price himself out of its 2023 and into another team’s October plans (or, in the Sox case, desperate hopes).

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Enrique Hernández

.209 AVG ⚾️ .613 OPS (69 OPS+) ⚾️ 4 HR ⚾️ 24 RBI ⚾️ 7.6% BB ⚾️ 16% SO

A fan favorite in Boston, Hernández also seems a highly unlikely trade candidate, particularly since they’re already got Jackie Bradley Jr.’s brutal bat as a DFA option if they need to trim fat in the outfield. That being said, while Hernández has spent the past month on the injured list with a right flexor strain, top prospect Jarren Duran has been a revelation in his second stint in the big leagues (135 OPS+ through 88 plate appearances) and former top prospect Franchy Cordero has finally broken through with solidly above-average hitting over the last two months. With Bradley’s glove still elite, Alex Verdugo firmly entrenched in right field and Trevor Story ensconced at the keystone for the next six years, there’s certainly a world in which a struggling Hernández simply has nowhere to play and the Red Sox are willing to entertain letting another team eat the remainder of the $7 million salary he’s earning on the back half of a two-year contract.

It’s probably not this world, and Hernández doesn’t do much to solve the problem of the White Sox lineup being terminally right-handed. Then again, the field of potentially available players who have proven that they can swing an above-average bat for a full season while playing both second base and the outfield with regularity is more or less nonexistent. If flexibility is the Sox endgame — why else try to make every first baseman in the system play the outfield? — then trying to pry Hernández might be a worthwhile endeavor.

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Stay tuned for part two, coming tomorrow with a series of relievers who you probably won’t be excited about, either.