How the White Sox Became a Chaotic Organization: Former Ace Jake Peavy Provides an Insider View

Jake Peavy // Credit: Jerry Lai-US PRESSWIRE

The Chicago White Sox are 36-118 this season with, mercifully, only eight games left to go. They must go 7-1 or better in this final stretch, otherwise they will tie the 1962 New York Mets for the most losses in a single season. A ballclub with a current winning percentage of 23% will almost certainly not win 87% of their remaining games, especially when you consider that 2/3 of those will come against opposition with winning records, and postseason position to play for.

That means we'll soon have a new official "worst MLB team ever."

Former White Sox ace Jake Peavy, who left Chicago in 2013 and then became the only starting pitcher to win two consecutive World Series in both leagues (2013 Boston Red Sox, 2014 San Francisco Giants), provided some deep and thorough insights into how this organization fell off a proverbial cliff.

"I don't want to throw people under the bus," Peavy said in an extensive and wide-ranging exclusive conversation with RG.org. "But it's just been a very slow to change and evolve (organization) and for a little bit, it doesn't seem to bite you in the butt, but after years and years and years and years of you not evolving with the rest of what the sport is doing, until you wake up one day with what you thought was a little problem, now you end up with a glaring hole."

The decline of the White Sox, who had already set numerous franchise records for losing, was slow and steady. There is blame to go all around, and naturally it must start at the top, with owner Jerry Reinsdorf.

Peavy, appearing on behalf of his partnership with Broken Top Brands, pointed out Reinsdorf's fatal flaw by doing so first by using the other team that he owns, the NBA's Chicago Bulls, as an example:

"He is loyal to a fault. He loves his guys so much, he sticks with them through thick and thin, a.k.a. Jerry Krause-Michael Jordan, I mean, who in their right mind lets Michael Jordan leave town?"

Arguably the most infamous decision in Chicago sports history, Reinsdorf ultimately sided with his then-general manager, Jerry Krause, who didn't get along with Jordan. Thus, the greatest basketball player of all time exited, and with that, the Bulls dynasty soon fell apart and never recovered.

Internal strife involving the most important figures within the organization is a theme with the White Sox as well.

"When I was there, Kenny [Williams] and Ozzie [Guillen], our general manager and manager, couldn't be in the same room," the 2007 National League Cy Young and Triple Crown winner said.

"The most successful teams that I've been on, the manager and general manager spent time together, hours together, every day making things go around - which is what successful organizations do."

"I love all those people, all those people are wonderful, but Herm Schneider got to stay there in charge [of the club's medical training staff] long after the rest of the world of training staff, and training rooms, and PTs and massage therapists, and all that stuff was coming on the scene.

"And everybody was evolving and analytics and science was making its way in, and the White Sox were doing none of that."

Baseball is a business, and in any company, if the CEO isn't leading properly, then all the department heads below can easily throw the organization into chaos.

Peavy then went on to describe the Sox as a ballclub with lots of people who were seemingly never on the same page.

"You look at Allen Thomas, strength and conditioning coach; there was not a cohesive plan between Herm Schneider, the training staff, and the strength staff. Herm disliked what was going on there [in the weight room].

"[Pitching coach] Don Cooper ran every bit of the pitching, where Ozzie didn't really do anything with pitchers. [Base coach] Joey Cora kind of made the lineup, while Ozzie talked to the media and just kind of sat above everybody's heads.

"Ozzie thought he was in charge, Joey thought he was in charge, Coop thinks he's in charge, Herm Schneider thinks he's in charge, him and Jerry are best friends, and he really trumps anybody in the room.

"Then you have a manager in Ozzie, who can't speak to Kenny Williams, can't even be in the same room. You're at a huge disadvantage, and we were like that for years, and that was just since I was there.

"Now you fast forward 10, 15 years of that stuff catching up with you. Every other team is now so far ahead, so you end up looking like this year's team.

"That's the true answer."

It's crucial that Peavy brought up the club's lack of attention to analytics and shying away from science. That's because even Williams himself, in a recent New York Times article profiling the club's devastating deterioration, admitted the Sox did not put much effort into analytics.

This was at a time when sabermetrics were taking off, and seam heads everywhere were praising Billy Beane's brilliant, ultra-emphasis on ROI work with the Oakland Athletics.

While Reinsdorf doesn't play "Moneyball," i.e. trying to maximize the return on investment in cost-effective players, he doesn't spend much on free agents either.

It's a worst of both worlds approach.

There are only two Major League clubs that have never spent $100 million or more on a single-player contract. The White Sox have never even topped $80M, as Andrew Benintendi's $75m deal, from December of 2022, is the richest player deal in Sox history.

Only the Athletics are lower, as Eric Chavez's $66m contract is the most cash that Oakland has ever splashed.

However, it's a grossly unfair comparison. That deal was signed in 2004, and when you adjust the Chavez contract for inflation, it's now worth well over $110 million.

However, there is still more going on here than palace intrigue, major internal strife, stubbornness to adapt and spending limits. You don't break a record for losses unless multiple major factors are going against you.

The joke here in local Chicago sports media is that whenever Reinsdorf looks to fill a new position at his ballclub, his executive search goes as far as the end of the hallway, and/or the contacts folder in his phone.

The recent hire of Chris Getz as general manager is a classic example. Peavy gave another one.

"And again, I love Robin Ventura with my whole heart, couldn't ask for a better guy, better friend, but when we let Ozzie go, and that era was over, and it was time to move on, you see who we got - Robin Ventura, straight off the couch," he responded.

The Mobile, Alabama native and San Diego Padres Hall of Famer coined his own phrase to describe the consistent chaos that often ensued within the Pale Hose clubhouse: "The situation is in charge."

He described one specific incident with the New York Yankees during a road game. The visiting clubhouse manager became highly frustrated by the lack of communication and organization within the Sox clubhouse as he tried to procure the tickets that players wanted to distribute to their people.

Let's say that the White Sox don't have a very clear "org chart."

Despite it all, Peavy consistently said throughout the interview that he truly loved his time in Chicago. The three-time All-Star described it as "an amazing city" and that his time with the Sox (2009-13) was "some of the best four years of my life."

Peavy currently works as an analyst for MLB Network alongside Alex Avila, a former Sox player. Peavy left Chicago three years before Avila spent his one season at 35th and Shields, but the two traded war stories about their time with the club and found some commonalities.

Peavy revealed what Avila told him about his time with the Southsiders:

"Stuff was going so bad with his hamstring rehabilitation that he just stopped going in the training room. He was on the injured list, and he stopped going to the training room, because the treatment was so bad. So he and Allen Thomas came up with a program, and he just went to him, and the weight room, everyday, for three weeks.

"And with that, and rest, a little bit of PT, he was ready to go. So he goes 'I walked in and told Herm that I was good to go, and then I went and told the staff I was good to go. And then I told the front office, so they activated me- that was the Chicago White Sox experience to a T.'

Peavy then summarized it perfectly: "Glad to see nothing's changed."

Reinsdorf has owned the team for 43 years, but he still appears to be an absentee landlord in many ways.