What would a Lance Lynn extension with the White Sox even look like?

(Kamil Krzaczynski/USA TODAY Sports)

Today marks the fifth anniversary of the James ShieldsFernando Tatis Jr. trade, which I only know because Baseball Twitter folks enjoy blowing the dust off that photo and marveling at it anew at various points throughout the baseball season.

Sending away Tatis in any trade was never going to age well, but Shields’ “contributions” are what truly make June 4 a day to live in infamy. It’d be one thing if Shields pitched as well as, say, Edwin Jackson. Jackson cost his own high price in Daniel Hudson and David Holmberg, and the White Sox didn’t get over the hump with him, but that was independent of Jackson’s own contributions. He pitched the equivalent of one full season with the Sox over two years, and went 11-9 with a 3.66 ERA over 30 starts and 196â…” innings. The Sox can say they got the highest concentration of the good version of Jackson among the 14 teams that have employed him. Other people were the problem.

Shields immediately, spectacularly, violently faceplanted, giving up 22 runs over his first three starts, including an inaugural shelling against Washington that sent the Sox below .500 for the first time all season. By the time he recovered for a decent July, it didn’t matter, and even if it could, he flopped against in August.

The immediacy of the White Sox’s scouting failure — which was foretold by FanGraphs before the trade — paired poorly with the Jeff Samardzija trade that went nowhere the year before. Samardzija gave the White Sox lots of innings, but the forced emphasis on his Northwest Indiana roots carried a certain sadness before he threw his first pitch, and he made no real impact on the White Sox when the games started. Zack Burdi, drafted with the compensatory pick the Sox received when the Giants landed Shark, is the only thing the White Sox have to show for the experience.

* * * * * * * * *

By those measures, the first two months of Lance Lynn are a huge relief, even if the Sox plan on there being at least five months left. Regardless of where he goes from here, he’s at least resembled the guy they thought they were getting. He’s 7-1 with a 1.23 ERA through 10 starts. He’s heaving varieties of fastballs 95 percent of the time, he’s sweating, he’s screaming, he’s thoroughly Lance Lynn. The White Sox finally got what they thought they were getting.

Sounds like the Captain of Attitude they always wanted.

If there’s one area where he’s not quite meeting the marketing, he’s only on pace for 170 innings. A steady flow of factors have conspired to cause him to fall off a workhorse’s workload — terrible defense early, a brief IL stint due to a back issue, a planned short-rest start that ended up getting rained out, and, on Thursday, another bout with general tightness, which he said was no big deal.

“They were sitting there talking to me like, ‘What do you think?'” Lynn explained. “And I was like, ‘Well, I want to go back out.’ They’re like, ‘Do you need to?’ And I was like, ‘Well, I want to.’

“But our bullpen was in a good spot with the day off (Wednesday). It’s good to give them a clean inning. And we won the game. … We’ve got an off day coming up on Monday, so hopefully nine outs isn’t too much for them to cover.”

Assuming this caution is really with October in mind, and not just a positively framed way of keeping him from revisiting the IL, he’s a great fit for this team. And if he’s a great fit for this team, he might be equally suited for future White Sox teams, especially since he’s one of two impending free-agent starters in the rotation.

Carlos Rodón is the other, and he seems like somebody who’s going to reach free agency. It’s hard to imagine a Scott Boras client bypassing an opportunity to hit free agency at the height of his powers, especially since Rodón’s track record is scarred enough that it might be hard to get a cost-conscious team like the White Sox to bid against themselves.

The analogue to me is Kevin Gausman, somebody who made good on a make-good deal during his sixth year of service time in 2020. The San Francisco Giants gave him the $18.9 million qualifying offer, which he accepted, and while there were some rumors that an extension was around the corner, he has not yet signed one. He’s driven up his price since then, riding two devastating pitches to a 6-0 start, with a 1.40 ERA supporting it.

If Rodón makes it through the rest of the year intact and has his best-ever season to show for it, a qualifying offer seems like a natural move — at least if there’s a qualifying offer to be made with the expiration of the Collective Bargaining Agreement looming.

* * * * * * * * *

With Lynn, it’s easier to see an extension.

Maybe.

He’s 34, and he’s already signed a couple of non-negligible contracts — a three-year, $22 million extension that covered his arb years in St. Louis, and now he’s in the final year of a three-year, $30 million deal originally signed with the Rangers. You could say that Lynn has shown that he doesn’t need to capitalize on his situation with a capital-C (which stands for “capital).

Then again, both of these deals preceded Lynn’s evolution into a pitcher worthy of annual Cy Young support, and he doesn’t have many peers as somebody who turned into A Guy in his early 30’s. Pitchers as good as Lynn is now were usually that good in their late-20’s, and signed a lucrative extension that covered them through age 35 and beyond. Justin Verlander is one example, signing a two-year, $66 million extension at age 36 as his first big deal approached its conclusion. But it’s fair to say Lynn isn’t Verlander.

There’s Charlie Morton, who has spun his renaissance into two contracts covering three years for $45 million, but he’s also somebody with a regulated workload and specific geographic requirements. Rich Hill‘s idiosyncratic profile resulted in a three-year, $48 million contract at age 36, even though he’s not a great bet for even 100 innings in a given year. Jake Arrieta was a late bloomer who signed a three-year, $75 million deal with the Phillies at 32, but he was three years younger in his first season and had a Cy Young to his name.

Perhaps the recent free-agent pitcher with the most similar situation was …

… wait for it …

James Shields, who carried a streak of eight consecutive 200-inning seasons into his first crack at free agency as a 33-year-old. He eventually signed with San Diego for four years and $75 million after an awkward amount of time on the market. By the time Shields’ age-35 season, he was on the White Sox’s books for two more long years, although the Padres were paying some of it.

What do you do with that information? You probably wait. I like Lynn’s chances of pitching toward 40, because with his ability to manipulate a fastball, he reminds me of Bartolo Colón, who succeeded at all sorts of velocities, ages and weights. But with a couple of bouts of tightness two months into the season, there are already a couple of events one could point to if Lynn suddenly started looking older and pitching less.

But there’s no reason to dwell on that yet, so let’s project a positive outcome where Lynn makes it three strong years in a row. A contract figure that comes to mind is three years, $55 million. That’s the deal Dallas Keuchel signed at 32, so it seems high. But Lynn would be coming off a string of healthier, fuller seasons, and he would also be free of a qualifying offer, so he could generate his own bidding war if his profile appeals to the analytics departments of teams with deeper pockets.

Then again, if Lynn hits free agency at full stride, that probably means the White Sox fared well as a whole themselves, which would generate the combination of goodwill and greater resources to make a postseason extension palatable for everybody. That’s when you can stop thinking about Shields, and instead picture a Jake Peavy situation where both sides met their objectives.

(Photo by Kamil Krzaczynski/USA TODAY Sports)

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Otter

Didn’t even really put this together until know, and it’s a long season yada yada, but the Sox would for sure give the QO to both Rodon and Lynn at this point.

I’ve got Lynn at 3/$50m… due to COVID related suppression.

theSKOT

The Sox can’t give Lynn a QO. With the current CBA, a player can only receive one QO and the Cardinals gave him one after the 2017 season. He turned it down and lost (turned it down at $17.4 million and then signed a 1-year, $12 million deal w/ Minnesota.)

Right Size Wrong Shape

If he turned it down then did he actually receive it?

HallofFrank

That number seems about right after Lynn’s good start. In the offseason, I was stumping for a ~3 year, $40-45m extension, but it’s fair to say the price has gone up.

calcetinesblancos

Yeah probably. But you also have to decide what number you could live with if there’s some regression due to age. This guy has also had conditioning issues in the past, which is not exactly reassuring as he gets closer to 40 than 30. His conditioning will scare other teams away too, or at least prevent him from getting longer contract offers.

If you could somehow get him to sign a two year deal for almost any amount, I would give him that in a heartbeat. Unless you really want to try and re-sign Los.

lifelongjd

The Sox really need to make a serious offer. Not only because of his performance and intangibles, there’s really no one else ready to take his rotation spot in the organization. Kopech is a great addition to the rotation next season, but I wouldn’t feel comfortable with Crochet, Stiever, or Lambert as the fifth.

karkovice squad

I don’t really envy the Sox having to decide what to do about the rotation with “if it ain’t broke, don’t fix it” providing some heavy psychological pressure. Plus wanting to make the most of having traded Dunning and Rodon’s peak.

As it stands, tho, they’ve likely got Gio, Cease, and Kopech fronting it with Keuchel probably still an expensive but serviceable 4/5.

So they could just try to expand the budget to bring 1 or both of them back, rebuild the bench, and fix whatever else needs it between now and then.

They could try to trade Keuchel to make that easier.

Or they could just try to find another 4/5 and some insurance arms.

Another White Sox case study for Keith Law and cognitive biases, maybe.

soxygen

Cease is not a top of rotation starter. And he’ll have to establish quite a track record of consistent performance to rebut that. I’m doubtful that he will over the remainder of this year.

The Sox should not go into 2022 assuming that Cease is a top 3 starter on a playoff team.

mikeyb

I really need to stop looking to see how Marcus Semien and Chris Bassitt are doing whenever Samardzija is mentioned here.

soxygen

Bassitt kills me. Ugh.

Semien less so. He had been an absolute butcher with the glove, the Sox had used a first round draft pick on Tim Anderson, and Yolmer was playing fairly well and rising fast. Not to say that he wasn’t a heavy price to pay, but the Sox were trading from an area of depth, and Semien’s defense was – to the eye test – really bad.

calcetinesblancos

Does anyone know how he felt about his time with the Yankees? If he’s looking for top dollar I’m curious how he’d feel about going back into the NYC fish bowl, either with the Mets or Yankees. A competitive team like the Sox that doesn’t come with that kind of pressure might be really appealing to him.

jhomeslice

I’d love to believe the Sox would pony up 3yrs/55 for Lynn (if that would be enough). But this gets into the dark side of their team, the ownership… which is why Eaton is our RF. I’ll believe the Sox will spend, when they are not ranked 15th in payroll. But Lynn should be their first choice to bring back, if they show willingness to spend next winter. As great as Rodon has looked, with his health history I can’t see giving him an offer like that. He needs to prove he can make it through this season without any time on the DL first, which would be a first for him, before they should have conviction that he would be a good multi year risk. Even if Carlos stays injury-free, I still think Lynn is a safer and better bet. A real shame they did not add a 1 year team option when they signed Rodon last winter!!

Last edited 2 years ago by jhomeslice
soxygen

Well, I think non-tendering him kind of ended any chance of that happening (if there was any chance).

I was a little surprised that they chose to do that. I get that they saved $1.0M to $1.5M. However, the biggest risk was health, and if he showed up for spring training and wasn’t healthy or effective enough to pitch in the majors they could have released him by March 15th and only been out 1/6th of his arb salary. To me it would have made more sense to tender and then go into spring thinking: he looks good we try to extend him a year, he looks OK or we have an embarrassment of riches and we use him in the pen, he looks hurt or awful and we release him.

Oh well. At least we saved $1.5M and we’re able to apply those savings to address the hole in right field. Sort of.

Last edited 2 years ago by soxygen
MarketMaker

the lynn-colón comp is what keeps coming to mind for me, too. injuries could certainly take a toll, but lynn is kinda the template in my mind for what a guy who pitches into his 40s might look like.

MarketMaker

looking at his numbers this season, i wonder if he’ll keep his extreme fly ball tendencies and HR/FB suppression intact. carrying a pretty crazy IFFB% and BABIP because of it.

joewho112

Mercedes at DH again tonight. No Sheets in the lineup. Lamb gets another LF start

jhomeslice

Disappointing. If Sheets isn’t going to start, seems like he would be better off at Charlotte. With Vaughn unlikely to be out more than a few games at most, seems strange to call up Sheets and then have him sit on the bench. If they start Lamb in left, give Sheets a try in right for a game or two, Eaton seems banged up anyway. Or give Mercedes a rest since he has been in a slump. They sure make some strange choices that nobody understands.

metasox

We don’t know what is going on behind the scenes. Batting practice, adjustments he is trying to make and so on. Maybe makes sense to give him a chance to do something

shaggy65

I’d rather we re-signed Rodon than Lynn, barring any major changes. I agree that Lynn would probably follow a Colon path of continued success with a slow decline, but I want more than that in our best contention years. Prime Carlos Rodon has more upside and I’m optimistic about his health going forward now that his delivery has simplified.

The best case scenario would be Carlos accepting the QO, but perhaps we could even get him on a high-value bridge contract–say 2 yrs/$50M. I just can’t see teams falling all over themselves to sign 5-year deals with a guy who has that injury history. The Sox obviously don’t have much history shopping at the high end of the pitching market, but they sometimes make exceptions for players being extended. Lynn would be fine, but I see Rodon as our best chance at an elite pitcher for that open spot.

Yolmer

You all are really low balling Lynn here. 3 years $75 million is an actual fair offer and may get an extension done. The guy is a workhorse and legit Cy Young contender. The Yankees or some other contender would offer at least that in the open market. He doesn’t really have any big injury concerns and at worst will be an above league average innings muncher if he regresses. I’d say 60% chance he stays basically this effective over the 3 years, 30% chance he becomes a LAIM, 10% chance he falls apart by the end of the deal.

HallofFrank

In the last 3 years, the only $75m+ pitchers in FA are Corbin, Cole, Strasburg, Wheeler, and Bauer. All were under 30. It doesn’t mean Lynn won’t earn that, but it seems unlikely—especially given pandemic-suppressed prices.

Plus, the extension is supposed to be a bit of a deal and not match what he’d get in the open market. An extension would insulate Lynn from some risk. If he has a bad second half or gets injured, his earning potential could plummet.

jhomeslice

I agree… not thinking he’s getting 75/3 on the open market, but who knows. If salaries go up a lot in general, which might happen with new tv contracts, then maybe. He could be worth that, if he keeps going like the past couple years and 2021. That would pretty much count the Sox out, as they have never gone over 20/year for anyone.

Yolmer

Lynn has more fWAR since 2019 than all of those pitchers except Cole. The guy is a top echelon pitcher. Sure, he is older, which is why I don’t think any team is going to go over 3 years, but he deserves an AAV in line with the top pitchers in the league because guess what he is a top pitcher in the league.

metasox

If I am reading this analysis correctly, it assumes Lynn finishes this contract and begins another. Not an extension from today. Was hoping the Sox would be able to reach a deal where the current contract is thrown out and he signs a new deal for 21-23, but that window may be closed.