White Sox trade deadline deal machine: Matt Moore, Tyler Naquin and other targets

Not sure anyone has mentioned this all season, but the White Sox are in a bit of a pickle.

They are in the middle of a contention window that will take some maneuvering to extend past 2023 (no shade to the long-term plan, but José Abreu, Yasmani Grandal, Lucas Giolito, Reynaldo López all hit free agency by then, with a host of club option decisions on deck and $24.8 million owed to Yoán Moncada in 2024). If not for their placement smack in the middle of that window, the 2022 team doesn’t seem like one worth mortgaging the future on. They just got over .500 for the first time since May and spent less than 24 hours there. Their run differential hasn’t been in the black since April. Struggling at defense, situational hitting and against right-handed pitching isn’t conducive to the big hot streak to which everyone keeps alluding.

But the Sox have actually stood up decently against top teams — if only out of their commitment to play decently all the time — and neither their best nor worst stretches of the season have done much to change their status from six hot weeks away from reclaiming the AL Central lead, and burying it somewhere on the South Side of Chicago until next March. They’re not selling. They’re not soft-selling. They’re not standing pat. Draft your reason why they should in the comment section, but they’re not doing it.

The pickle is that with Colson Montgomery — consensus top-100 prospect at this point, playing at High-A Winston Salem — and Oscar Colás playing at a similarly high level at Double A, the Sox actually have a chip or two in a way they didn’t last year, when they traded pop-up prospects and injured/struggling major league pieces to fill their needs.

But right now, those two are also the Sox’s primary tools for un-jankifying the post-2023 picture. Those chips are the heart and spine of their improving but still slight farm system. And another way the front office could show trust in the team is a 2021 Atlanta-style deadline, where a slate of role player additions surround a core that is still expected to get healthy and rolling, eventually, at some point.

“It is always a power boost when you make a move, no matter if you’re on a winning team or a losing team,” Grandal said. “When you make a move, it shows trust in the team. It shows trust in the ability of the players have and all they’re trying to do is help us out to get to where we want to be. This is a fun time in baseball, right when the deadline is coming.”

Here, we will simulate that Atlanta-style deadline with the help of The Athletic writers Levi Weaver, C. Trent Rosecrans and Rob Biertempfel, plus a surprise and underwhelming mystery guest.

Step 1: Acquire starting pitching depth by trading for José Quintana of the Pittsburgh Pirates

Why we’re doing this: Because we missed him! Er, because counting on Lance Lynn rebounding from knee surgery, Michael Kopech setting a new single-season high in innings with every outing, and Lucas Giolito ironing out his mechanics all at the same time feels dicey. Johnny Cueto’s peripheral-defying magic, and Dylan Cease also rocketing past his career-high innings by September, don’t quite feel like sure enough things. At 33, Quintana is having a renaissance season with a 3.70 ERA in 97 1/3 innings since all of a sudden he is preventing home runs at a rate in line with his career prime. Hmm, hmmm.

Biertempfel: The Pirates’ window for being a playoff contender should begin to creak open by the 2024 season. Some of the club’s better prospects finally reached Triple A this year and several others are not far behind. Like every club, the Pirates crave more pitching depth. Twelve of their 21 draft picks this year were college pitchers. The Pirates also could use help at first base, preferably somebody with a good on-base rate and some power. Their options at the big-league level beyond Michael Chavis are limited. Daniel Vogelbach was traded, Yoshi Tsutsugo is a flop and Mason Martin is batting .196 with a 38 percent strikeout rate at Class AAA. Let’s be real about Quintana — he’s a rental player, a bounce-back guy with decent numbers who would shift to a bullpen role on a good team’s playoff roster. The Pirates would do well to acquire two players for him; hopefully, one of them will be close to major league-ready.


Would the White Sox trade for old friend José Quintana? (Kim Klement / USA Today)

The deal: Quintana for 3B Jake Burger and High-A right-hander Cristian Mena

Ooh, Rob makes a good point. Quintana could also add a multi-inning lefty to the bullpen come crunch time. Garrett who? (I’m kidding, Garrett. Get well soon). Burger saved the White Sox’s bacon several times this season, but a healthy version of their roster has a big at-bat crunch for right-handed corner types who are weaker against right-handed pitching, and this has not been a good year for Burger’s defensive versatility prospects. Mena is having a breakout season with a clear feel for a plus curveball at age 19, but will need to add strength and velocity to take it to the next level, which is a bit more of a long-term project.

These losses — the cost of acquiring any starters at the deadline — would sting and be somewhat controversial since it seems unlikely the Sox would task Quintana with a playoff start. They also currently have five healthy starters that don’t figure to be moved or dropped anytime soon. But there are too many risk factors to ride out the final two months with just a Davis Martin-shaped safety net. One scout called this package “a hair above market value, which is probably what’s needed,” which I took as an endorsement, a little judgmental, and a sign they would like to be done fielding my questions about this.

Step 2: Acquire left-handed relief help by trading for left-hander Matt Moore of the Texas Rangers

Why we’re doing this: 1.74 ERA in 46 2/3 innings with one home run allowed to 184 batters faced and fairly neutral platoon splits. The 33-year-old is a pure rental on a one-year, $2.5 million deal. Aaron Bummer is likely out until September.

Weaver: Moore has been a nice surprise for the Rangers this year, armed with a new curveball that has boosted his effectiveness considerably. He’s also a free agent at the end of the year, and he’s 33. I’m not sure there’s a good reason not to trade him if any team wants to make a non-insulting offer. Trust your scouts, take a flyer on a 20-year-old kid in A-ball who they think has some upside, and sign off. How about Wilfred Veras and Andy Atwood?

I would be very interested to know more about Atwood’s story. Twenty-five-year-old free agent, signed in late June, and is killing it in Low A?

Sure.

The deal: Moore for Class-A outfielders Wilfred Veras and Andy Atwood

In reality, a lot of the trades could look like this, where opposing team scouts recommend some long-shots that have more interesting ceilings than some slightly well-known names. Like Mena, Veras is also 19 and pretty far away at the moment, but is having a fun year at Kannapolis showing off his athleticism and pop with 15 home runs in 79 games. There are questions about the hit tool and the near-30 percent strikeout rate that keep the Sox from penciling him into their three-year plan. Atwood was signed last month as a free agent, turns 26 in November and is killing at Low A, so him getting included in a deadline deal would basically be a pinnacle achievement for the pro scout who recommended him.

Step 3: Acquire a left-handed corner outfielder by trading for Tyler Naquin of the Cincinnati Reds

Why we’re doing this: A .278/.338/.503 batting line vs. right-handed pitching since the start of 2021. Definitely not a plus-fielding defensive outfielder, but an experienced one rather than a converted first baseman. It’s another pure rental on a $4 million deal.

Rosecrans: Tyler Naquin was a nice pickup before the 2021 season, signing him to a minor-league deal before spring training. He earned a spot on the squad and the team agreed to a one-year deal with him for just more than $4 million, avoiding arbitration in what is the 31-year-old’s final year of arbitration before free agency. The Reds like Naquin as a player, but he’s not likely to be re-signed after this season, so it makes a lot of sense to get something back, even if it’s a lottery ticket of an arm.

The deal: Naquin for Class A right-hander Kohl Simas

Simas has definitely been the best performer from the crop of undrafted free-agent signings from last July and has a case for the most consistent starting pitcher at Class-A Kannapolis. But a healthy organization is uncovering and developing these sorts of prospects for trade ammunition on a yearly basis to fuel continual contention, so that simple but necessary moves like finding someone who can stand in right field and pop pitches into the right-field seats in the right matchups can be added.

And with that, we haven’t fixed everything, and haven’t made a big splash, but we have strategically addressed some obvious needs in a seller’s market without yielding any marquee prospects. The core players of this team still have to drag it to the promised land (or 10 games over .500, whichever comes first), but the work is all done. Pour a drink, light a cigar. It’s time to relax.


But something… isn’t right, is it? This team needs a spark, doesn’t it? After Wednesday’s meltdown in Denver saw Joe Kelly leave with a bicep flareup, it certainly should need more than one reliever, and our Orioles writer Dan Connolly is going to talk me into giving up a haul for closer Jorge López on Friday. But more than that, when have we seen a contending White Sox team deal value for nothing but rentals, when they so clearly value extra years of control to be part of another clear contention season in 2023? And if this front office really wants to boost a flagging offense and not just fall into the same problems with right field next season, maybe angrily reciting Naquin’s platoon splits to anyone who will listen isn’t enough.

Also, don’t they have to do something that kind of hurts? Or make a deal with someone less than desirable?

With that in mind, I contacted our Cubs writer Sahadev Sharma about what it will take to acquire switch-hitter Ian Happ, who hits free agency after 2023.

Fegan: This is a safe space to deposit your decidedly non-Colson Montgomery packages here. What’s that, you say? Bryan Ramos, Norge Vera and José Rodríguez? How excited are you already?

Sharma: Taking Montgomery off the table will ruin any attempts for the Cubs to start a trend of trading for players they passed in the draft a year later. But their next favorite activity is adding high-upside international talent they couldn’t secure. So this is intriguing, but it also may just be difficult to get done when the reality is the White Sox farm system still isn’t intriguing overall. It may make more sense for Jed Hoyer to just call A.J. Preller and see if he can keep him engaged long enough to finalize a deal.

Fegan: Dammit, Sharma get back to the table! Preller is too busy trying to get Juan Soto to listen to Jed blab to him about podcasters.

What if, instead of serving as a bridge to Oscar Colás, Happ actually brought in Colás to headline a package? Hell, take any Cuban minor leaguer you want. The Sox are a central Indiana pipeline team now. Also can you please give me a reason why Happ is not going to turn into a 30 percent strikeout rate guy all over again?

Sharma: Building a deal around Colás definitely makes sense, especially if the Cubs believe he can have a similar offensive impact to Happ. As much as grabbing high-upside 19-year-olds has been their m.o. of late, picking up a Double-A outfielder who could reasonably arrive in the big leagues late next season or by 2024 makes much more sense to try and speed up this rebuild. As far as Happ goes, he’s made real changes to his setup and swing, leading to him being able to close a big hole at the top of the zone. Once well below-average when it came to swinging and missing at fastballs up, Happ now is right at league average. He’s never been big on chasing much else besides that, so this development has really transformed him into a different player. He doesn’t seem to have as much pop, at least so far, but he’s much more consistent and more productive overall. Some once wondered if he should stop switch-hitting due to his struggles from the right side, but that no longer seems to be an issue either.

Fegan: I can’t imagine that Jed texts Rick, “I dunno, Preller probably can do better” three times per day, because they seem to get along and have made multiple major deals with each other, whereas I never want to talk to you again. But could Colás, Gavin Sheets (give the people of Wrigley some dingers!) and right-hander Sean Burke close this deal?

Sharma: Haven’t you heard, everyone wants Happ! But you’re adding MLB-ready, left-handed pop to the deal, which the Cubs definitely need, and now you’re throwing in a projected multi-inning reliever who has stuff over command? Whoa, whoa, whoa, this is far too tempting for the Cubs. I think the first deal you offered may not be much worse than this one, but I guess the fact that there’s one guy in this who actually has made the big leagues is a plus. I’m tempted to take this. But wait a minute, is that Preller calling? Oh no, it’s actually Ross Atkins. Or maybe it’s Alex Anthopoulos. Whatever, point is, the Cubs have options here and looking at this farm system for multiple days while having to deal with you has made me depressed.

The begrudging deal that is almost solely to demonstrate how painful acquiring an impact, multi-year piece would be: Happ for OF/1B Gavin Sheets, Double-A outfielder Oscar Colás and right-hander Sean Burke.

Life is suffering.

(Top photo of Matt Moore: Tim Heitman / USA Today)