This White Sox rebuild can’t hinge on extensions

Contentious negotiations may make free agent years harder to pry away from players

Earlier this week during the Cubs’ Yu Darvish celebration, Theo Epstein made a comment that stuck in the side of my brain:

“When we acquired Jose Quintana, we made the point then that acquiring him with the great contract he had might allow us at some point to bring another pitcher with him,” Epstein said at the Cubs’ spring training home in Mesa on Tuesday. “We almost felt like we were acquiring one-and-a-half pitchers in that deal, because it would go halfway toward acquiring someone else. I think today is that day when you bring in a Yu Darvish.”

Immediately and masochistically, I thought about the White Sox having four of those contracts, or two extra players in Epstein’s view. The Sox failed to even get to .500 with that head start. Missing with such a great margin for error is a big stain on Rick Hahn’s record, and I interpret some of his SoxFest humility as though he’s smiling with gritted teeth and saying to the person next to him, “Why don’t they hate me more…“.

Setting self-flagellation aside, it also sounded like a public assessment from Cubs personnel that Quintana had signed for too little. I bet Quintana knows — and I doubt he cares — that fans and media had turned his name into a synonym for “huge bargain,” but it tends to stick out when somebody on the same payroll does it.

Usually the polite way to talk about great contracts is by focusing on the stability such a signing generates, which has the benefit of being both true and something that appeals to the player for priorities personal and professional. Here, seeing Epstein effectively say, “We used money Quintana didn’t capture and directed it toward another great pitcher” is a little blunter, a degree lower than Jeff Samardzija politely but firmly regarding the idea of signing a contract extension as harmful to his peers.

This context seems worth keeping in mind, as characterized in a comment by karkovice squad on Patrick’s offseason grades:

Also seems like the possibly new file and trial arb strategy might have deserved some more comment. Especially since it might be accompanied by a shift in team and player willingness to negotiate extensions which was a particular strength for the front office that enabled rebuild 2.0.

Indeed, Yolmer Sanchez and Avisail Garcia became the first White Sox to go to arbitration hearings since 2001, and both did so over six-figure sums. Sanchez pleasantly deflected a question about it, and I haven’t seen a (no-)comment from Garcia on the matter, but here’s Marcus Stroman serving as a reminder of the way these things can make bad blood boil:

(Stroman deleted the tweet. Tim Anderson might have something to say about Stroman’s alleged “thick skin.”)

Hahn said that he talked with Sanchez and Garcia and said it wouldn’t affect the way the Sox viewed them, and on the players’ side, they both reported to spring training before they had to.

Yet Hahn also sounded miffed, irked and maybe even rankled by the development, saying the Sox “didn’t receive offers that even looked like the filing number.” If the GM’s characterization of negotiations is accurate, then it might not bode well for other negotiations in which the player risks forgoing future earnings, even if the money lost doesn’t seem all that significant.

This isn’t to say that Tim Anderson and Nate Jones signed the last team-friendly extensions for the foreseeable future. There will be other guys with young families to consider and other players whose health may prevent them from waiting until a big payday to cash in. While Sale and Quintana missed out on millions, they’ve never seemed to regard themselves as victims in any sense. OK, Sale might’ve been peeved, but more by the White Sox’ inability to take advantage of the head start he afforded, the kind that Epstein hailed with Quintana.

Then again, the real test of their tolerance will come when they hit free agency years after they were supposed to. If this market marks the start of a trend of 30ish-year-old players getting less than they wanted — and if Manny Machado and Bryce Harper are handsomely rewarded for going year to year — then it stands to reason that early career extensions will be harder to strike.

This doesn’t greatly affect anything the White Sox are doing right now, because they have Yoan Moncada, Lucas Giolito and Reynaldo Lopez for the next six seasons, and Michael Kopech and Eloy Jimenez for at least a seven-year window. Even if every single one of them hits free agency as soon as possible, the Sox should have made the postseason multiple times by then.

In the short term, though, it might have helped the Sox resist the temptation of splurging earlier. Taking a shortcut didn’t work the last time, even with the huge cushion those bargain contracts provided. If the White Sox aren’t counting on extending the duration of this first line of young talent in the same way they tied down Sale, Quintana and Adam Eaton, then it makes sense to form arrange second and third waves in the prospect ranks before any costly long-term decisions are made.

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Jim Margalus
Jim Margalus

Writing about the White Sox for a 16th season, first here, then at South Side Sox, and now here again. Let’s talk curling.

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On the other hand it may be signalling a shift in gambling more dollars on younger players than over 30 players. While there is risk involved for teams to give long term deals to the youngsters, there seems to be an awareness now that there is greater risk in big contracts to older veterans. We may start seeing more generous offers on extensions and less generous free agent offers.


Tell that to under 30 year old Mike Moustakas and Eric Hosmer


I also told them they should have accepted the qualifying offers.

karkovice squad

Thanks for covering this at greater length.

I expect there to be few early extensions signed between now and the new CBA across the league. It also seems likely that trend won’t reverse very much after the CBA.

From a business perspective, the Sox decision to rebuild exactly when they did, as well as to extend Anderson so early, seem to either be incredibly fortuitous coincidences or amazingly prescient. Not that I’ll forgive them for giving the Twins the chance to send the Yankees to the ALDS.

Greg Nix

I bet we still see extensions across the league, but tilted more towards role players and lower round draft picks. For example, if Delmonico has a good year I don’t see him turning down $20 million guaranteed, but it’s unlikely Moncada makes the same decision even for twice as much.

karkovice squad

I think players like Delmonico were already going year to year. And not by their own choice. There just isn’t much risk of breaking the bank in arb, especially off a single peak year that’s merely “good.” So they don’t have the leverage to get guaranteed money.

Plus, he ain’t exactly a spring chicken as rookies go. So an extension would be buying out likely decline. He loses leverage there, too.


I think we’ll see extensions that buy out arb years, giving teams some cost certainty. But far fewer players willing to give up any FA years.

Lurker Laura

Love how the Stroman-Anderson feud keeps popping up.


It feels like the teams are looking for a sweet spot of not too old, not too young and not to expensive.


Solid dating philosophy too.


Doesn’t what Theo said directly contradict Samardzija’s claim that signing an extension would be detrimental to his peers?

Here we have a player (Quintana) who’s extension allowed another team to enter the market for one of his peers (Darvish).

karkovice squad

Darvish’s contract coming in below where the market was even a year or two ago is probably also a factor.

And I think we have to consider that the Cubs also paid in prospects for the part of Q’s value not covered by his salary.


The jury is still out whether those Anderson and Jones extensions are team-friendly or not. The Padres couldn’t wait to get out of their extension with Jedd Gyorko.
Each party is taking a risk when signing or not signing an extension. The players who are studs the moment they get called up are going to be advised not to sign them, the other 99% are assessing different risks with their representation. We can’t ignore the fact that Joe Crede was offered a multi-year extension and Scott Boras advised against it – costing Crede a lot more than it cost Boras. But we don’t call Boras’ decision “team-friendly” in hindsight.


Team options aren’t team-friendly, they’re just options. The value of the options is what makes them friendly or not. Jones has historically produced about 2 WAR per year when healthy. 2 WAR at the present rate is about 5-7 million, which is roughly what the options call for. If he’s healthy, he gets paid roughly the market rate, if he’s not healthy he gets the league minimum. That’s fair for both sides, unless he has an atypical monster season.


Fangraphs likes to push the linear value of cost per WAR, but no teams are actually pricing players that way. The reason for this is simple supply and demand. There are a lot of 1 WAR players available, a fair amount of 2 WAR players, fewer 3 WAR players, etc.

Teams are pricing the first WAR at 2-3 million, the second WAR at an additional 3-5 million, the third WAR at an additional 5-7 million, etc. Two WAR players are getting in the 5-8 million range for the most part, and Jones is in that vicinity.


I’d like to point out that those four contracts DID allow the Sox to sign Melky Cabrera, Adam LaRoche, David Robertson, and take on Todd Frazier’s salary. (All while eating Keppinger’s contract.) A big stain for sure since they didn’t produce much, but it isn’t like Hahn didn’t try to the spend the savings like Epstein is doing – he just chose badly, very badly.


Kind of.

Those four contracts enabled the Sox to pay $144.5m for those five combined. One of those contracts enabled the Cubs to pay $126m for Darvish.


No. One of those contracts enabled the Cubs to offer another 30 million to Darvish. Without Quintana they might have had to push harder for Lynn or Cobb, but it didn’t open up the entire 126 million.

Trooper Galactus

Know what else enabled the Cubs to sign Darvish? A payroll well over $180 million, so basically $50 million (i.e.-two elite players) more than the White Sox ever spent.

Patrick Nolan

Players are gonna want to see how the CBA shakes out before locking in so many future salaries…makes sense.

Trooper Galactus

Then again, don’t you think a few might try cashing in as much as possible before that?

karkovice squad

The players’ sense seems to be that the market conditions which made extensions a good idea have shifted against them. Unless they’re Harper, Machado, et al, they’re already not going to get paid when they hit free agency. So until there’s a new CBA to change the market, giving up dollars at arb and/or delaying free agency by signing away free agent years isn’t worth the temporary job security.

Rex Fermier

I don’t feel bad for any of the players that signed extensions. The signing was a gamble for both sides. The players had professional management advising them as to whether the deal was a good one or not. Players can be good for a few years and then, suddenly, without warning, fail. Either by blowing out an arm or some other unpredictable career changing injury. A long term contract guarantees money, BIG MONEY, no matter what happens.

Trooper Galactus

I don’t have any statistics in front of me, but I’d hazard to say that extensions work out to the team’s benefit FAR more often than the player’s. Yeah, they get that financial blanket a bit quicker, but looking at what’s happening now they could be costing themselves a LOT down the line; tens of millions probably. Teams are certainly saving more frequently by offering extensions and getting value performance than they are getting burned by players getting hurt or stalling out in development. The financial benefit absolutely favors the teams in the end because the financial risk/cost of a failed extension is vastly less than a nine-figure contract for a veteran free agent.