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Worst White Sox Trade Ever?

Was the trade of Fernando Tatis, Jr. in 2016 for pitcher James "Big Game" Shields the worst deal in White Sox history? The short answer is "yes," or at least "probably." However, these puzzlers never are simple. Investigation and hindsight are required.

Upon first glance, the Sox traded a 17-year-old prospect for a pitcher in the twilight of his career. The kid, now 21, just got a historical 14-year contract from the San Diego Padres which will pay him $340 million. The pitcher, Shields, is long gone from the game while the youngster is poised to lead his teammates for more than the next decade as the legitimate challengers to the vaunted Dodgers.

Imagine if general manager Rick Hahn, who has admitted the folly of his ways, hadn't made this deal almost five years ago. Just think if Tatis was playing alongside Tim Anderson today in the Sox infield, joining the mix of other young athletes like Yoan Moncada, Eloy Jimenez, Luis Robert, Lucas Giolito, Dylan Cease, Michael Kopech, Reynaldo Lopez and Garrett Crochet.

Surely in the 120-year history of the South Side franchise no front office made such a grievous error. Nevertheless, the situation back on June 4, 2016 provides perspective about Hahn's thinking, which did have a sliver of rationale.

At that time Tatis Jr., son of Fernando Sr., a very good player for 11 years in the major leagues, hadn't made one dime playing professional baseball. In fact, he never even appeared in a game in the White Sox system before the trade to San Diego.

Sox scouts sang the praises of the young Tatis, but at the time the White Sox perhaps were a pitcher or two away from challenging for a post-season position. They had started the 2016 campaign winning 23 of their first 33 games, good for a six-game lead in the Central Division. While they cooled off, they still were 29-27 on June 4, two games behind front-running Cleveland, the eventual AL champions.

Meanwhile, Shields was in the second year of a four-year $73 million deal with San Diego, the biggest contract in team annals until Padres chairman Peter Seidler, who happens to be the grandson of Walter O'Malley, the villain who moved the Dodgers out of Brooklyn, opened his coffers to snag Eric Hosmer and Manny Machado.

Shields had fallen out of favor in San Diego so much so that part of the deal included handing over $38 million - not an inconsequential amount - to help Hahn pay for Big Game James. At the time Chris Sale and Jose Quintana occupied the top of the rotation for the Sox, and developing 25-year-old lefthander Carlos Rodon, the number three pick in the 2014 draft, provided another acceptable starter. With closer David Robertson covering the ninth inning, you couldn't fault Hahn if he thought the addition of Shields was a reasonable option to improve his ballclub.

The Sox threw in pitcher Erik Johnson, who as it turned out would need Tommy John surgery before the season ended. Johnson had pitched well in six starts in 2015, but had been demoted to Triple-A after two disastrous outings at the start of the '16 season, the last time he pitched in the major leagues. Apparently he was damaged goods.

With time to mature and develop, Tatis has been everything White Sox scouts predicted. In the past two seasons and 143 games, he has slashed .301/.374/.956 to go along with 39 homers and 98 RBIs. Not to mention that the kid is an exciting shortstop who plays the game with unlimited enthusiasm and moxie. Oh, to be 21, multitalented, with a future lying in wait to see just how high this kid can fly.

Meanwhile, Big Game James was a Big Time Flop in parts of three seasons for the White Sox. His final start in San Diego lasted less than three innings and 20 batters, 10 of whom scored. Shields' ERA that afternoon ballooned from 3.06 to 4.28 and hastened his departure.

Nevertheless, Shields, 34 at the time, had been a workhorse throughout his career. For nine consecutive seasons before coming to the South Side, Shields had posted double digits in victories and an average of 221 innings pitched per season. He was the epitome of an innings-eater, although there was no guarantee of the quality of those innings.

Once ensconced on the South Side for the next four months, Shields struggled mightily, just as he did in his swansong appearance in San Diego. Instead of solidifying the starting rotation, he more or less blew it up. In 22 starts, Shields went 4-12 with an appalling 6.77 ERA. The next two seasons weren't much better, as James dropped 23 of 35 decisions with a 4.78 ERA. Whether the trade measures up to Brock-for-Broglio remains to be seen, but Tatis-for-Shields is part of the same neighborhood.

In his time with the White Sox, we fans were reminded how good Shields was in the clubhouse, how he mentored younger pitchers. That was code for, "The guy can't pitch."

After the acquisition of Shields, things quickly fell apart for the Sox along with the throwback Sox uniforms that Sale dismembered about six weeks after Shields' arrival. Before the season reached a merciful ending, the club slipped below .500, manager Robin Ventura resigned, and soon thereafter a wholesale rebuild began.

One might argue that Shields' futility hastened the decision to rebuild, which clearly has turned out to be a wonderful development. Had Shields pitched effectively for the Sox, even propelling them to an October berth, the overhaul of the roster may never have happened. Sale and Adam Eaton might have been retained along with Quintana in 2017. Some or all of the team's bright young players may never have worn a Sox uniform. The Shields-Tatis exchange opened the door to a new era. Considering that scenario, the trade was a savior, a stroke of good fortune. Thank you very much, James.

So returning to the original question, we would need to look at other White Sox deals before labeling the dealing of Tatis, Jr. as the lowest of the low.

After the pennant-winning season of 1959, owner Bill Veeck dealt most of his prized young prospects for veterans whom he felt would provide enough pop to repeat as American League champions.

Hence trades were made to bring Minnie Minoso back home after two years in Cleveland along with Roy Sievers, one of the American League's elite power hitters, who had been toiling for the cellar-dwelling Washington Senators. Gene Freese was brought in from the Phillies to play third base via a trade for 20-year-old Johnny Callison, who went on to make three National League All-Star teams during his 16-year career. Meanwhile, Freese, who was allergic to ground balls, played one year for the Sox before being dealt to Cincinnati. Veeck also dealt catchers Earl Battey and John "Honey" Romano, both of whom became very capable backstops for Washington-Minnesota and Cleveland, respectively. The Sox never had a really talented catcher again until Carlton Fisk arrived in 1981.

First baseman Norm Cash, 25, also went to Cleveland and eventually played 15 years in Detroit, amassing 377 home runs and winning the batting title in 1961 with a .361 average. The Sox lineup, in fact, was more imposing in 1960, but the pitchers performed far less effectively, and, let's face it, the Yankees simply had a bad year in '59. They were by far the best team of the era. The departure of all those prospects arguably could have been the nadir of White Sox bartering.

Upon Veeck's second go-round in the '70s, he had two hard-throwing young pitchers in Terry Forster and Rich "Goose" Gossage. Veeck packaged both in a swap for outfielder Richie Zisk prior to the 1977 season, the summer of the South Side Hitmen with Zisk's 30 home runs and 101 RBIs leading the way. This was Bill's rent-a-player scheme, and Zisk predictably departed Chicago after one season, signing a big contract with Texas. Veeck simply didn't have the funds to retain the slugger, who, by the way, never matched his '77 season during six more major league seasons.

As for Gossage and Forster, Goose is in the Hall of Fame while Forster was a top relief pitcher for 16 seasons.

Was the trade of Gossage and Forster a mindless, foolish decision? Well, the Sox won 90 games in 1977; the team drew 1.6 million; Nancy Faust began her "Na Na Hey Hey Goodbye" serenades; Oscar Gamble thrilled us with the long ball and his Afro; beer flowed in oceans; and everyone had a grand time.

While Hahn might flagellate himself over the decision to trade the young Tatis, he apparently has given himself and his organization a second chance. There is another Tatis in the pipeline, Elijah, 19, a middle infielder whom the Sox signed in 2019 for a $400,000 international bonus. Chances are the younger brother is no Fernando. Chances are better that this time Hahn will wait to find out.

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Former Bill Veeck bar buddy Roger Wallenstein is our White Sox correspondent. He welcomes your comments.

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