White Sox offer outline if they look out, dead by trade deadline

(Photo by Kamil Krzaczynski/USA TODAY Sports)

On Sunday morning, as the White Sox were set to improve to 4-2 in May and 5-2 in their last seven, Bob Nightengale spent a few paragraphs of his latest notebook explaining how the Sox will try to break it down if they can’t mount a real challenge in the AL Central.

It starts with the Rangers, whose inability to hold late-inning leads might have them looking for high-leverage help this summer.

If the Rangers wait, they could pick up veterans Joe Kelly or Kendall Graveman if the Chicago White Sox are out of the race by July. 

– The White Sox don’t plan to keep starter Lucas Giolito after this season, and will make him available at the trade deadline if they are out of the race. 

– The White Sox certainly plan to pick up the $15 million option on closer Liam Hendriks in 2024 considering the buyout is also $15 million. 

These feel like Jerry Reinsdorf’s truths, particularly the one pertaining to Giolito. Rick Hahn publicly adopts a never-say-never stance with impending White Sox free agents no matter how thick and layered the writing on the wall, whereas if we can assume that Reinsdorf still conducts himself the way he did decades ago, then you can just apply his 1997 quote about catching Cleveland to re-signing any White Sox player who may command considerable money on the open market.

Giolito’s camp probably doesn’t see a long-term future with the White Sox either, so I doubt that particular sentence alters any relationships. Nevertheless, a team normally wouldn’t want to invite that conversation when they have bigger immediate crises, but since Reinsdorf doesn’t grant local audiences, he’s never required to participate in conversations he starts.

The note about Hendriks also caught my attention, mostly because “certain” and its various forms aren’t words I’d associate with his season as he works his way back from beating non-Hodgkin lymphoma. Maybe he’ll be able to slide back into the closer role after a ramp-up period, or maybe that ramp-up period will last the rest of the year.

If it struck me as unexpected, it’s because the White Sox seemed bizarrely proud of the way that contract was structured. Reinsdorf took a victory lap for it, telling Nightengale back in 2021, “There was no way I was going to commit to a regular four-year contract,” and yet here the White Sox are, treating it like a regular four-year contract.

The reasons run the gamut. If you’re willing to assign the kindest and most compassionate motives, the White Sox don’t particularly care to wield Hendriks’ cancer battle against him financially, and that wouldn’t be out of character.

But you could also imagine the White Sox choosing a similar course even if Hendriks didn’t experience this particular detour. Let’s go back to Reinsdorf’s stated reasoning for the massive buyout.

“While I knew we weren’t really going to save any money,’’ Reinsdorf said, “the reason I proposed 10 years it is that it would give us some cash flow relief. The player would get the same money he was going to get, but if we had to let him go, I didn’t want to have a $15 million payment for the year if we had to replace him. It just made it easier to absorb the pain if we had to let him go.

The White Sox won’t have to worry about cash flow relief in a scenario where they’re rebuilding, resetting and/or retrenching. In that case, they’re better off paying Hendriks $15 million on a greatly reduced payroll and seeing if he brings back anything on the trade market during the year, rather than having an extra $1.5 million payment to negotiate in years where every dollar matters, especially if José Abreu is already receiving $1 million in deferred salary through 2026.

The situations regarding Kelly and Graveman are far simpler by comparison, as both have to be healthy and pitching well in order for any team to care. In that scenario, Kelly strikes me as the more desirable option because his contract expires after the year, whereas Graveman is owed another $8 million in 2024.

Think of it in terms of the Jake Diekman trade, which wasn’t a mistake if viewed only in terms of talent. The White Sox could’ve used a credible lefty reliever and Reese McGuire was the out-of-options catcher other teams might’ve wanted. That much was fine, even if it would’ve been nice to retain McGuire.

The problem was that Diekman showed signs of slippage while being owed $3.5 million the following year, followed by a $1 million buyout, meaning the Sox ran the risk of buying into a decline out of desperation. That’s what made it immediately regrettable, and I imagine teams less addicted to acquiring relievers would prefer the shorter commitment, all things being equal. These discussions are merely theoretical for the time being, with the hope that things like the White Sox’s winning percentage won’t remain the same weeks and months from now.

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If they are out of it in July, I would expect a full-scale sell-off. No way cheapskate Jerry is going to want to pay any of those guys with attendance almost assuredly dropping. Giolito- gone. Grandal- gone. Lynn-gone. Kelly-gone. Maybe even Timmy and Hendriks-gone. Then none of the players’ options picked up in the future. And the return on those guys will be miniscule compared to the returns from the last sell-off. So for those of you who want them to do a mini-rebuild now to reload for 2024, no way Jerry does that. Kenny will blame the fans for not showing up and causing them to shed salary. And they will be back to 2016-18 levels with no light at the end of the tunnel.

There are only two good scenarios going forward. 1. They actually return to contention in this putrid division and add at the deadline as attendance climbs. 2. Jerry gets rid of the team. I don’t see any other scenario that would be good for the long-term health of this team.

Augusto Barojas

For fans to settle for contending in a putrid division, not dominating it but merely having basically a long shot chance to win it, is so wrong there are not words for. I don’t see fans showing up in any numbers for that, knowing the phony and slimy motives of the whole FO. Fans are sick of this bullshit, and the fake and cheap people behind all of it. I seriously could not wish for a scenario where Jerry gets playoff revenue with a team that wins 79 games, with his and Hahn’s piss poor efforts, phony narratives, cowardly cancellation of Sox fest, and basically lying to the fans faces – for years. The division is an embarrassment, as is the depth of this roster, and anybody can say what they want about anything happening in the playoffs, I will say “not with this team”, or this division for that matter.

I think even if they are within some semblance of a long shot of “contention”, the over riding factor will be the poor attendance and significantly disappointing/declining revenue that Jerry gets. I think highly probable we will see another white flag trade(s) even if they don’t fall to 12-15 games out or something. I think your first couple sentences are what will most likely happen, and this team probably won’t see another playoff game until close to 2030. Unless Reinsdorf dies or sells quickly by some miracle.


I’m not saying that I would be happy with an 80-win division champ. But we have no say in the matter. JR will do whatever he pleases. He couldn’t care less about the fans. But the last thing I want is another Rick Hahn or Chris Getz-led rebuild. I’m too old for that.

Augusto Barojas

It’s just a needlessly depressing situation. Even Jerry derived some happiness in 2005 and even 2006, I’m sure. He has all the money in the world and won’t spend any of it to bring excitement and happiness to this city – or even himself.

My loyalty and interest in this team is seriously waning. It’s basically a psychological disorder at this point, I don’t know why I can’t completely wean myself away from this pathetic team!


I’m not going to root against the Sox because Jerry owns the team. I will let Jerry get all the accolades he wants if it means the Sox catch lightning in a bottle and win the World Series.

Augusto Barojas

Are you going to seriously suggest that THIS team could win the World Series, this year? You should be a comedian.

To Err is Herrmann

I can’t tell if I’m a Sox fan or a SoxMachine fan. I suspect the latter.


My unborn grandchildren are too old for that.


I’m a little confused. You say you’d expect a “full-scale sell-off,” but only list players on expiring contracts (with “maybe” for guys whose contracts expire next year). Wouldn’t that be exactly a “mini-rebuild now to reload for 2024?” But you also say “no way Jerry does that.”

I actually think a “mini-rebuild + 2024 re-tooling” is the most likely scenario. The expiring contracts are gone at the deadline. They listen to offers on TA and Hendriks. But they don’t do a “full-scale sell-off” or full rebuild. In other words, I think they keep Robert, Vaughn, Cease, and the like and try again next year. I’m not saying that’s the prudent way forward, especially if they cut payroll again. But it’s also not completely crazy (in theory, but maybe with this crew running the show, it is). They have (by my back-of-the-napkin math) around $70m coming off the books.

Augusto Barojas

I agree that they probably won’t trade Robert, Vaughn, Cease. Everybody else is fair game including Yoan and Tim. I think your assessment is correct on that. But “try again next year”, they haven’t tried since 2020. I don’t see them maintaining what for Jerry is a high payroll, and signing free agents equivalent to the contracts they are shedding. They will lose 3/5 of their rotation in Gio, Lynn, Clevinger. I doubt they sign more than 1 decent free agent starter, if that. It will probably be someone who hasn’t pitched well since the Cubs won the World Series.

I think they will be back in wait and see mode again, hoping that Colas, Sosa, Montgomery, Ramos, Mena can come up and pan out, and then possibly adding again if at some point they are lucky enough to have a good young core. I think the departure of guys leaving at the end of this year means that they will tank 2024 as well, and that the soonest they would “do” anything would be the winter prior to 2025. After 2024 they are shedding like 110M or something with Tim, Yoan, Liam, Graveman being gone in addition to Grandal/Lynn/Gio. They will have payroll flexibility to do whatever they wanted, but it’s hard to have much faith that they will operate like a good ownership would anyway. As many have said, it’s a pretty grim outlook until Jerry dies or sells.


You’re right Augusto. If they shed payroll at the deadline, they are NOT going to retool for 2024. Jerry will slash payroll and the next young wave will slowly trickle up over the next couple of years. And that will be without 7 top 100 guys in the system like Hahn acquired during the last teardown. You’d maybe see 2 or 3 top 100 guys added.


I agree things are grim until Jerry dies or sells. I don’t agree that “they haven’t tried since 2020.” They are clearly trying to win. I think the Sox FO really thought they had the best team in the central this year. The FO is just so bad that they can’t assemble a good team even when trying.

I also think JR will cut payroll. But it wouldn’t surprise me if the payroll was around $160m or so (down about $20m from this year). I think they add 2-3 “win-now” players this upcoming offseason (even if they don’t allocate the money the way they should). Aside from Giolito, the guys falling off the payroll are mostly good for the team.

Of course, the kind of re-tooling I’m describing—cutting some payroll and keeping the FO intact—is probably an awful decision. They could even win the central, but it’s hard to imagine this producing a sustainable winner. I think they do it, though, because to do otherwise is to admit total defeat. Even the Sox FO sees the writing on the wall: Sox fans are not going to endure another full rebuild right now.

Augusto Barojas

The best free agent they’ve signed during the whole rebuild is a slightly above average outfielder who hit 5 homers last year. In 3 years. You and I have drastically different ideas of what constitutes “clearly trying to win”.

And having a goal of winning a piss poor division and having a team that might actually win a playoff series for the 2nd time in 50 years are two different things. This team has little chance of doing the former and virtually none of the latter. They are not trying, at all.


I’d argue that Grandal worked out well, but your point stands that they haven’t been willing to spend much beyond what they offered a 30-year-old catcher who had caught 153 games the year before (and I think had a case of the yips in the playoffs?).


You’re moving the goalposts to make this about how much ownership spends. Do you think the Rays are trying to win? Their ownership spends a lot less than JR. Obviously, they are just way better at winning. Their trying goes a lot further.

How about this for a definition of “trying to win?”: fielding a team you really think will win your division and is a world series contender. If that’s not “trying to win” for a FO, I don’t know what is. Some FO try harder than others, obviously.

The point is: if they trade all their best players for prospects and drastically cut payroll, they can no longer say with a straight face they are trying to win. I don’t think they’ll do that in ’24. I think they’ll try to field a team they think will win. I’m not saying they will or that it’s a good idea to do so.


It might be a stretch to say they have fielded or will field a team in ’24 they “think will win.” Might be more precise to say they would field a team for which winning is at least plausible.

Last edited 17 days ago by JazznFunk

Is Jerry stupid enough to cut salary and have no “glitz” to draw fans if 2023 continues to be a poor draw?

Trooper Galactus

If they cut payroll another $20 million they’ll only have about $20 million to add anybody new unless they trade guys like Anderson, Hendriks, Benintendi, or Moncada. If everybody is retained, they’re looking at about a $140 million payroll in 2024 with three starting pitchers, a starting catcher, and multiple relievers to replace, and that’s assuming guys like Colas and Sosa can become viable options before then.


It’s already over 140M in 2024. By my calculations making some arb assumptions it’s at 160M, assuming Lynn/Kelly/Diekman don’t get picked up and TA does.

There are details like Benintendi making $8.5M more next year than he is this year, Robert/Moncada/Eloy/Bummer making more, 7M in buyouts.

If they cut payroll 20M (so 190M to 170M) they’d have about 10M to spend.

Alfornia Jones

I think this is the right take. They’ve spent $370 million over two years for less than .500 results. Jerry needs a break for a couple years.

They might as well volunteer to tank in 2024.

Trooper Galactus

I think the plan from the get-go was to trade Yoan before the final season of his deal. They were probably hoping Burger could take the reins so they could just couch trading Moncada (who I’m sure they saw as a centerpiece to their contention window while he was cheaper) as an effort to retool the lineup.


“Market value” contracts fetch next to nothing, so if this was truly Hahn’s plan, then yeah, that explains why he hasn’t been able to pull off a noteworthy trade in over a year and a half.


You’re probably right that there will be more than those guys go. I just listed the guys whose contracts are up in 1-2 years. A few of Moncada, Eloy, Robert, Cease, Kopech, Vaughn could go also. Nobody else on the team is worth anything.

Last edited 18 days ago by roke1960

If it’s a full-scale rebuild, then all of those guys are going. There’s no reason to keep any of them. Maybe you’re right that we’re heading there, but that’s too hard for me to imagine at the moment. I think the strategy will be (for good or ill) to keep the long-term guys around and re-tool for ’24/25.


They have money coming off the books, but also a number of guys with rising salaries due to guaranteed contracts (Benintendi a big example by his contract structure, also Robert, Eloy, Moncada) or arb (Cease, Vaughn, Kopech). Plus a lot of buy-outs (including 4M for Clevinger, plus Kelly, Diekman, Lynn). By my calculations, if they let Giolito, Grandal, Lopez walk and decline options on Lynn, Kelly, Diekman, and keep TA, they’d be at around a $160M payroll. If they only have $20-30M to address 3 SP, the bullpen, 2B, RF, and C, that’s not going to work given they have no legitimate star players.


The total amount of those rising contracts plus buyouts is around $27m. By my calculations, they have about $77m coming off the books.

Yeah Colas and Sosa are definitely your RF and 2B. No reason to “address” the bullpen if they are picking up Hendriks’ option. They might sign a catcher, but I’d expect a cheap veteran. So I think it’s more like we’re looking at $15-20m to address SP—and that’s if they decide to cut payroll.

Don’t get me wrong: I hope they don’t. I’m just saying I think this is most likely. They’ll “re-tool” by adding a SP or two, and some veterans.


JR won’t sell. His heirs will. And said buyer will want a new stadium in Chicago (LOL) or move the team to Nashville or Salt Lake. We might get an expansion team if that is the case and GRF is still standing. MLB would probably want two teams in Chicago.


I’ve been thinking about this hypothetical for the past few weeks. Just a thought experiment, since it’s not going to happen. But honestly, faced with the choice between continuing to support the JR-led White Sox for several more years or allowing the franchise to relocate and getting an expansion team in Chicago, it’s not hard to make a case for the latter.


There is zero chance of this team relocating to Salt or Nashville

The White Sox have the third largest regional television deal in baseball. There is zero chance of replicating that in Nashville or Salt Lake.


I agree. Why would major league baseball let the White Sox if they are doing everything they can to keep the Rays in Tampa and the A’s in Oakland?


100% agree — there is no way this franchise is relocating. Speaking purely as a hypothetical though, it’s interesting to think about how your fandom would be affected and what you would prefer.

Augusto Barojas

I agree. Such talk is silliness, I think. If an estute prospective owner looked objectively at the history, he would notice that they drew almost 3 million fans in 2006 after they won the WS. This IS a large fanbase. With one of the worst team histories in sports. Just get an owner with some money, balls, and who wants to win and the money and fans will be there for sure. I can’t see an owner wanting to buy the team and move them to a smaller market.


You don’t even have to go back as far as 2006, in 2021 the Sox were 5th in the AL for attendance and could likely have drawn close to around 3M were the COVID restrictions not in place for much of the season. Chicago is a viable market for two baseball teams if you run the organization properly.

As Cirensica

This division is so bad, we might still be 8 games under .500 by July and be 5 games behind. The “out of it in July” comes in many shades in the ALC.


I expect more then a couple relievers and Gio if they are really out of it by the deadline. If Nightengale is already laying the groundwork like the good little mouthpiece he is, they are gonna be shedding a lot

I keep having a hard time pegging what Giolito’s next contract may look like, seems like the numbers could be all over the place and he has obviously the most important 4-5 months of his financial career ahead of him. Assuming he is healthy and finishes up in the range of a 3.75 era… probably 5-100 to 7 and 150… does that seem crazy? Berrios got 7 for 131 and was just 2 years younger at the time, rodon got 6 for 162 …. degrom 5 for 185 … tijuan walker 4 for 72


I could see him getting pretty good money. He’s inconsistent, but he’s been pretty good for long stretches and he isn’t hurt constantly.


The obsession the Sox have with insignificant details that nobody else could give a shit about if they tried (such as that weird Hendriks contract) will never cease to amaze me.

Greg Nix

If there was ever an illustration that Reinsdorf cares more about money than baseball…

Torpedo Jones

100%. That’s one of those overarching themes of Jerry’s ownership – that he perceives his top adversary to be the players, rather than other teams. Winning games is nice, but not as nice as winning negotiations against labor.

He’s like a really boring and wrinkly super-villain in that way. Punishing players for having the nerve to be paid what the market will bear and, in turn, punishing Sox fans who want the team to actually compete with any regularity. Strong Mr. Burns energy with him….


Based on his most recent comments, he considers himself FAR above other owners and wouldn’t stoop to claiming that they could compete with the great JR.

Greg Nix

Two sides of the same coin. He’s not as straight-up cheap as some owners, but it all goes back to that “business environment that makes sense” quote.


It may not be an obsession as much as a required FO work around JR’s unwillingness to pay market rates.


I agree that the Sox contract structing seems odd. I’ve often wondered if JR has set up annuities that cover his payroll. It could be that the Sox are hamstrung in pursuit of free agents by having to work through investment agencies as much as by simple cheapness. Given that, under the Allyns and Veeck, simply “meeting the payroll” occasionally proved a challenge, JR (and his minority investors) may have signed on to some sort of long term payroll strategy that plays out strangely. Over-paying Leury, inflexibility when dealing with Machado, locking young talent into fixed contracts early, and the like, suggests some sort of “insured payroll” plan that may have made sense when JR bought the team and the MLB player’s union was on the verge of forcing a radical restructuring of the financial landscape; but, now, it yields questionable utility.

Last edited 18 days ago by Denman

Diekman was a TLR hire because he wanted a LH relief pitcher, period. Lucas is probably gone come Aug.1. Best of luck in his new endeavors. Lynn and Grandal are likely gone, too, Lynn more so. Kelly is a better mid-season trade candidate than Graveman. Liam will depend on his health and effectiveness. TA is more likely an off-season trade deal.

But the real question is whether this FO can maximize the value back this summer or next winter, and the track record is not good.

As Cirensica

The White Sox won’t have to worry about cash flow relief in a scenario where they’re rebuilding, resetting and/or retrenching.

I swear I read the last word as retching. In my brain, it fits. It just does.


I still want them to compete for the division

As Cirensica

Me too. I know I am delusional, but I can’t help myself.


I didnt follow the Hawks much growing up, but is it fair to paint Jerry as like the Bill Wirtz of MLB owners? No way Wirtz could have survived MLB ownership, he would have to evolve into an Uncle Jerry


Different motivations and ideologies.


As woeful as the latter day Sox have become under JR, I don’t think they hold a candle to the Bill Wirtz Hawks.

For all his many flaws JR still can point to 2005 (and the Bulls championships). Bill Wirtz’s Hawks teams never won a Stanley Cup. Wirtz traded away all the Blackhawks’ stars in the 90s (Chelios being the last in 99) and got basically nothing in return. You think the Sox are bad now, that 99-2007 Hawks run… phew. Bill Wirtz ended the Hawk’s 30 year streak of making the playoffs. The Sox have been capable of producing legit stars even if they field some bad teams, but those early 2000’s Hawks teams were pretty devoid of talent and brutal to watch. Tony Amonte, Eric Daze, and Alexei Zhamnov were fine players but not stars.

Last edited 17 days ago by vince

I guess I should resign myself to a very ugly rotation in ’24 whether the Sox are pretending to compete or not. We’ll have Cease, Kopech, Martin and then who? Stiever? If we aren’t even planning to shop at the Giolito end of the market then I can’t wait to see which two Ivan Nova’s we sign.


Burke, probably, since he’s at AAA. Would make sense to try the Crochet-as-starter experiment if they still wanna do that. Possible ’24 midseason call-ups would be Cannon (advanced & polished, likely quick mover) and Mena (obv very young, but if he’s gonna buzz-saw thru AA like this…)


I have a different take on the Hendriks thing. If it were just about money, then from a present value standpoint the wise thing to do would be the annual payments. To think about how you’d implement that, you could literally make the 2024 payment and then buy treasury bonds with the remainder.

My guess is that Jerry now wants a relatively clean ledger in case he sells. He might be worried that a potential purchaser will be turned off by an accumulation of future obligations, and his desire for a clean sale is what is driving this otherwise irrational position.

It’s just an educated guess, and a guy can always dream.


No matter what they decide, if Hahn’s the one making the calls, why should we expect different results?

Trooper Galactus

Credit Hahn with creating a minor league pipeline so devoid of usable talent that he had to sign a zillion major league players who washed out of the league just to field a viable Triple-A squad.