The last White Sox rebuild: Bobby Howry remembers aftermath of '97 'White Flag' trade

The last White Sox rebuild: Bobby Howry remembers aftermath of '97 'White Flag' trade

Bobby Howry wasn't aware of the fact he was part of one of the more infamous transactions in White Sox history until a few years after it happened. 

In 1997, with the White Sox only 3 1/2 games behind the division-leading Cleveland Indians, general manager Ron Schueler pulled the trigger on a massive trade that left many around Chicago — including some in the White Sox clubhouse — scratching their heads. Heading to the San Francisco Giants was the team's best starting pitcher (left-hander Wilson Alvarez), a reliable rotation piece (Doug Drabek) and a closer coming off a 1996 All-Star appearance (Roberto Hernandez). In return, the White Sox acquired six minor leaguers: right-handers Howry, Lorenzo Barcelo, Keith Foulke, left-hander Ken Vining, shortstop Mike Caruso and outfielder Brian Manning. Only Foulke had major league experience, and it wasn't exactly good (an 8.26 ERA in 44 2/3 innings). 

Howry was largely oblivious to the shocking nature of the trade that brought him from the Giants to White Sox until, before the 1999 season, he was featured in a commercial that referenced the "White Flag trade."

"I don't even know if I knew it was called that before then," Howry recalled last weekend at the Sheraton Grand Chicago at Cubs Convention. 

The trade was a stark signal that youth would be emphasized on 35th and Shields. Both Alvarez and Hernandez were set to become free agents after the 1997 season, and the 40-year-old Darwin wasn't a long-term piece, either. With youngsters like Magglio Ordonez and Carlos Lee rising through the farm system, the move was made with an eye on the future and maximizing the return on players who weren't going to be long-term pieces. 

Sound familiar? 

It's hardly a perfect comparison, but when the White Sox traded Chris Sale to the Boston Red Sox in December for four minor leaguers — headlined by top-100 prospects in Yoan Moncada and Michael Kopech — it was the first rebuilding blockbuster trade the organization had made since the 1997 White Flag deal. Shortly after trading their staff ace at the 2016 Winter Meetings, the White Sox shipped Adam Eaton — their best position player — to the Washington Nationals for a package of prospects featuring two more highly-regarded youngsters in Lucas Giolito and Reynaldo Lopez. 

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And there still could be more moves on the horizon, too, for Rick Hahn's White Sox (Jose Quintana has been the subject of persistent rumors since the Winter Meetings). But for those looking for an optimistic outlook of the White Sox rebuilding plans, it's worth noting that the club's last youth movement, to an extent, was successful.

Only Howry (3.74 ERA over 294 games) and Foulke (2.87 ERA, 100 saves over 346 games) became significant long-term pieces for the White Sox from those six players brought over in 1997. And it wasn't like Schueler dealt away any of the franchise's cornerstones — like Frank Thomas, Albert Belle and Robin Ventura — but with future starters in Lee, Ordonez and Chris Singleton on their way the White Sox were able to go young. A swap of promising youthful players (Mike Cameron for Paul Konerko) proved to be successful a year and a half later. 

And with a couple of shrewd moves — namely, dealing Jamie Navarro and John Snyder to the Milwaukee Brewers for Cal Eldred and Jose Valentin — the "Kids Can Play" White Sox stormed to an American League Central title in 2000. 

"It was great," Howry said of developing with so many young players in the late 1990's and 2000. "You come in and you feel a lot more comfortable when you got a lot of young guys and you're all coming up together and building together. It's not like you're walking into a primarily veteran clubhouse where you're kind of having to duck and hide all the time. We had a great group of guys and we built together over a couple of years, and putting that together was a lot of fun."

What sparked things in 2000, Howry said, was that ferocious brawl with the Detroit Tigers on April 22 in which 11 players were ejected (the fight left Foulke needing five stitches and former Tigers catcher/first baseman Robert Fick doused in beer). 

"About the time we had that fight with Detroit, that big brawl, all of a sudden after then we just seemed to kind of come together and everything started to click and it took off," Howry said. 

The White Sox went 80-81 in 1998 and slipped to 75-86 in 1999, but their 95-67 record in 2000 was the best in the league — though it only amounted to a three-game sweep at the hands of the wild-card winning Seattle Mariners. 

Still, the White Flag trade had a happy ending two and a half years later. While with the White Sox, Howry didn't feel pressure to perform under the circumstances with which he arrived, which probably helped those young players grow together into eventual division champions. 

"I was 23 years old," Howry said. "At 23 years old, I didn't really — I was just like, okay, I'm still playing, I got a place to play. I didn't really put a whole lot of thought into three veteran guys for six minor leaguers." 

Don Cooper's 'eyes lit up' watching White Sox prospect Michael Kopech

Don Cooper's 'eyes lit up' watching White Sox prospect Michael Kopech

There are bittersweet emotions because he's no longer Chris Sale's pitching coach, but Don Cooper is excited about the future of the White Sox.

The team's veteran pitching coach joined the White Sox Talk podcast on Tuesday and said even though he's sad see Sale go, it's hard to overlook the talent the team has received in return. Last month the White Sox traded their five-time All-Star to the Boston Red Sox in exchange for four prospects, including Michael Kopech. The club also added Lucas Giolito and two other pitching prospects in a trade for Adam Eaton. 

"When I saw Kopech, my eyes lit up," Cooper said. "Not only is he a big strong son of a gun, the stuff out of his hand is really good, life, energy stuff. He's just untapped talent right now. He's 20 years old. But he's already moved up the scale. 

"Delivery-wise it was like, 'Whoa.' Everything I like, he does. ...

"If he stays healthy he has a chance to be a killer."

Cooper also has high hopes for Giolito, baseball's top pitching prospect in 2016, who posted a 6.75 ERA in six big league games last season. He discounted Giolito's struggles as a small sample size and hopes to maximize the pitcher's talent.

"He still has his good stuff," Cooper said. "We've got to mix it up. We need more strikes. We need more consistency."

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Cooper also noted that the stuff of Reynaldo Lopez, acquired with Giolito and Dane Dunning from Washington for Eaton, caught his eye. Combined with the pitching prospects already in the organization, Cooper thinks the White Sox have a talented farm system.

"Looking around, all of a sudden, combined with the younger pitchers we had in the system already, the injection of these guys that Rick (Hahn) has traded for, it's giving us a stronger, stronger system," Cooper said. "We’re amassing a lot of good talent."

Cooper said Sale is the most talented pitcher he's ever coached and he'll miss their everyday relationship. He described Sale as one of the 10 best pitchers on the planet. But Cooper hasn't been surprised by any moves since the White Sox allowed Mark Buehrle to leave via free agency. 

"It's sad that Chris is gone because my individual everyday relationship with him is over as a coach," Cooper said. "But the exciting thing is one of the reasons, the excitement of the guys you get back in return.

"It was mixed. 'Listen man, I'm sad you’re leaving because of that, the relationship. The everyday relationship is no longer there. We're friends.' I know this guy. I've seen every pitch in the big leagues he's thrown. 

"When you get to see every pitch and you're with them every single day and that relationship is over, it's sad in some ways. But this has happened before. It happened to Buehrle. If it can happen to Buehrle, it can happen to everybody."

Why the Yankees are the perfect trade partner for White Sox Jose Quintana

Why the Yankees are the perfect trade partner for White Sox Jose Quintana

Recent reports suggest the prospect-hungry White Sox received a recent inquiry from the New York Yankees about the availability of All-Star pitcher Jose Quintana.

According to one analyst, there’s nobody that general manager Rick Hahn would rather hear from than Yankees counterpart Brian Cashman when it comes to the possibility of trading Quintana, who is affordably signed through 2020 and has produced 18.1 Wins Above Replacement the past four seasons, according to Not only might the Yankees need Quintana now more than ever,’s Jim Callis opines, they possess the top farm system in baseball and could absorb the high cost.

A first-time All-Star in 2016, Quintana has received similar hot stove attention to Chris Sale and Adam Eaton, each of whom was included in a blockbuster trade at the Winter Meetings earlier this month. The Houston Astros and Pittsburgh Pirates have also reportedly shown interest in Quintana, one of baseball’s most productive starting pitchers over the past four seasons. Set to earn $36.85 million through 2020 if both his team options are exercised, Quintana could be worth as much as Sale.

While Callis said on’s most recent White Sox Talk podcast that he isn’t certain New York would part with shortstop Gleyber Torres, the club has three other top prospects (all are ranked in the Top 22 on’s current top 100) around which to build a package.

“If I’m Rick Hahn, I want to be talking to Brian Cashman about Jose Quintana,” Callis said. “That would be the No. 1 team to matchup with because of need, desperation, value prospects they have. You could make a really nice deal there.”

The White Sox have already done extremely well with the returns for Sale and Eaton, who brought back seven prospects, including four currently ranked in’s Top 30 (Yoan Moncada, Lucas Giolito, Reynaldo Lopez and Michael Kopech).

Though he doesn’t possess the same arsenal as Sale, Quintana has a 3.35 ERA since 2013 and one more year left on his deal than Boston Red Sox ace, who is signed through 2019. That extra season could have Quintana in the same value range as Sale, who netted Moncada, the top position player prospect in the majors, Kopech, who has drawn comparisons to Noah Syndergaard, toolsy outfielder Luis Basabe and pitcher Luis Diaz, who has a good fastball.

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Hahn and the White Sox have attached a premium price to Quintana and aren’t inclined to deal him unless its met. With five of seven prospects acquired being pitchers, its believed the White Sox would like to acquire another big bat and are more focused on position players.

Five of the Yankees’ top six prospects are position players, including, Torres, outfielders Clint Frazier, Aaron Judge and Blake Rutherford and infielder Jorge Mateo. Rutherford is ranked as the No. 51 prospect in’s Top 100 and the rest are in the Top 22.

While the Yankees need another starting pitcher, speculation continues that the club may prefer to hang onto its top prospects, many of whom were acquired last July in trades for Andrew Miller, Aroldis Chapman and Carlos Beltran. The general message out of New York has remained consistent the past six months: The Yankees like their farm system and aren’t too eager to dip into it.

Still, Callis thinks the club could feel more pressure to make a move. Not only are the Red Sox with Sale a strong contender for the pennant, the Yankees have only a 2015 wild card loss to Houston to show for the past four seasons. The team’s lack of success could hurt both its cable ratings and its ability to draw fans. Even if the Yankees have to pay the premium for Quintana, Callis thinks the system is deep enough to handle such a move.

The entire scenario has Hahn in a good place.

“That’d be the perfect team to engage because I think the Yankees have the best farm system right now and the deepest,” Callis said. “The Yankees can make that trade and still have a good farm system and really improve their big league club.

“I do think teams value their prospects, but they also value winning. You’ve got to catch a team in the right cycle. Just using the Yankees for example, yes they went out an acquired prospects. But viewership on the YES Network was down. And if the Yankees aren’t winning, people aren’t going to pay for the YES Network. They have to win.”

“What they did was good for the long-term future of the franchise. But if the Yankees win 80 games this year and miss the playoffs again — they’re not going to be able to keep doing that. They’re going to go all in and start trading these guys.”