Despite both being original members of the American League, the Yankees have a relatively limited trade history with the White Sox, swapping fringe players and executing low-impact purchases for most of their history. While the White Sox’s’s now-perpetual place at the bottom of the standings is a relatively new phenomenon, the Yankees have typically done the team pretty dirty on the trade market, giving me plenty to think about for the Best Trade category and not a lot for the Worst. Let’s get to it!
February 24, 1948: The White Sox trade Fred Bradley, Aaron Robinson, and Bill Wight to the Yankees for Eddie Lopat.
The first big splash between the two teams came before the 1948 season, when the second division and cash-strapped White Sox decided to sell high on their breakout star pitcher. Some things never change, huh. Anyhow, they sent him to New York as a 30-year-old for a package highlighted by right-handed pitcher Bill Wight, who gave the Sox an even 10.0 fWAR in three seasons before a trade to Boston. Neither Bradley, also a right-handed pitcher, nor Robinson, a catcher, contributed much of anything to the Pale Hose, and none of the three players had any real MLB playing experience at the time of the trade.
Wight might have been a solid contributor for a moment, but as we know, it pales in comparison to Lopat’s contributions to the Yankees. Lopat pitched eight seasons and nearly 1,500 innings in pinstripes, accumulating a 113-59 record, a 3.19 ERA (121 ERA+), and 19.5 fWAR. He picked up five rings along the way, making seven World Series starts to the tune of a 2.60 ERA. All in all, picking up a rotation stalwart for a team that ran the league for a decade — and the 80th-greatest Yankee overall, according to all of us — for little of consequence ranks as the best trade ever (for New York, of course) between these two.
July 31, 2004: The Yankees trade José Contreras to the White Sox for Esteban Loaiza.
The overall trade history here is pretty banal, but when accounting for context, this probably sticks out as the worst thing on the record sheet. After a decorated Cuban career, Contreras arrived in New York amid much fanfare, signing a four-year, $32 million contract and making the team’s preseason Sports Illustrated cover. His first year with the team was truncated by injury but he looked worth the investing, picking up seven wins with a 3.30 ERA, 3.21 FIP, and as many strikeouts as walks.
However, 2004 was a different story. The 31-year-old struggled mightily, attracting media ire as he posted a 5.64 ERA through 18 starts amid a heated division title race with Boston. Brian Cashman cut bait at the trade deadline. The Yankees needed pitching help, but as it turned out, Esteban Loaiza was not the answer. Loaiza was the Cy Young runner-up in 2003, putting together one of the wilder one-hit wonder seasons in recent memory with a 21-9 record, 2.90 ERA, and league-leading 207 punchouts. He never came close to doing that again, and he was a disaster down the stretch for the Bombers, getting lit up for 42 runs in 42.1 innings.
Nonetheless, Contreras broke out for the White Sox, playing a pivotal role in the rotation for the team’s 2005 championship and making an All-Star appearance in 2006.
The veteran accumulated 15.2 fWAR over parts of six seasons in Chicago, and won back-to-back AL Pitcher of the Month awards in September 2005 and April 2006. Loaiza was more or less done after 2004, and the Yankees spent subsequent years with names like Jaret Wright, Shawn Chacon, and Kei Igawa in the rotation. Sure could have used José.
Most Overlooked Trade
January 5, 1987: The White Sox trade Pete Fillson and Randy Velarde to the Yankees for Mike Soper and Scott Nielson.
Velarde is one of my favorite types of player: the solid-but-unexceptional bench morale guy who sticks in one place for a long time just because he makes himself useful and everyone kind of likes him. Velarde appeared in nine straight seasons for the Yankees to start his career despite only twice playing more than 95 games in a season. He played just about every position on the field, and despite struggling with the stick to start his career, turned into a more-than-capable hitter after establishing himself in the mid-1980s, running a 106 OPS+ in his last four years with the team. Buck Showalter called him something like the ultimate team player, and you can thank the White Sox for it. It cost virtually nothing, as Soper never reached the big leagues and Nielson gave them just 19 games of 6.24 ERA pitching.
April 5, 1977: The Yankees trade Bob Polinsky, Oscar Gamble, LaMarr Hoyt and $200,000 to the White Sox for Bucky Dent.
December 14, 1994: The Yankees trade a player to be named later and Keith Heberling to the White Sox for Jack McDowell. The Yankees sent Lyle Mouton to the White Sox to complete the trade.
I’m putting these two together because first of all, whichever one didn’t make it here was going to wind up in Other Trades of Note as it is. It’s not because of Oscar Gamble, who came and went from New York in rapidity, being acquired in 1976, traded in 1977, and re-acquired in 1979. It’s not because of Bucky Dent, the 89th-best Yankee, and it’s not because of Lyle Mouton, who had a solid three-year run as a backup outfielder in Chicago. In fact, you can even bring the Loaiza trade down here. The weird part is that ever since the Cy Young Award split between leagues, two White Sox have taken home the trophy, and both were involved in trades with the Yankees.
If it wasn’t for Dent’s legendary contribution to team history and overall solid production, this one might rank among the team’s worst, as Hoyt led the league in wins for two straight seasons and took home the 1983 Cy Young. A decade later, Black Jack McDowell repeated the feat in another division-winning year on the South Side, only to make his way to New York a year later amid a dispute with management. Sweet serendipity, huh?
Other Trades of Note
June 1, 1913: The Yankees trade Hal Chase to the White Sox for Babe Borton and Rollie Zeider.
Some of his contemporaries called Chase the best first basemen they’d ever seen. Known for being perhaps questionable in character and facing suspicions of throwing games, the Yankees unloaded Chase to Chicago. 1919 wasn’t the first time they picked up a Babe from the Sox!
January 10, 1992: The White Sox trade Domingo Jean, Mélido Pérez, and Bob Wickman to the Yankees for Steve Sax.
One of the better moves on this list, Sax was a highly-touted acquisition for an ascending White Sox team, but the Yankees sold high at the best possible time. After an excellent three-year run in New York, itself after three All-Star appearances in Los Angeles, Sax flopped with the Sox, developing the yips and running a 69 OPS+ in two years on the South Side. Pérez gave the Yankees a six-win season in 1992, and Wickman was a solid bullpen contributor for parts of five seasons before becoming a part of the deal to land dynasty bullpen contributor Graeme Lloyd. Not too bad!
November 13, 2008. The Yankees trade Wilson Betemit, Jeff Marquez, and Jhonny Nuñez to the White Sox for Nick Swisher and Kanekoa Texeira.
Probably the second-best move on this list, fan-favorite/Top 100 Yank Swisher was acquired by the White Sox for a set of top prospects prior to the 2008 season, but was essentially dumped by the team after his relationship soured with the clubhouse and temperamental manager Ozzie Guillén. Betemit lasted just one year in Chicago, but Swisher was a key part of the 2009 champions and is still an active presence in Yankees life today.
July 19, 2017: The White Sox trade Todd Frazier, Tommy Kahnle, and David Robertson to the Yankees for Ian Clarkin, Tito Polo, Tyler Clippard, and Blake Rutherford.
This one worked out pretty well too. Frazier didn’t wind up being a difference maker, but Robertson (clearly) still had plenty of use in him just two-and-a-half years after leaving the Yankees, while Kahnle is still around today following a detour to LA. They were key to the 2017 club’s playoff run, and New York might never have escaped the AL Wild Card Game without them.
Nobody was particularly sad to see Clippard go, and the Sox turned around and traded him again after just 11 appearances. And for all the fanfare, Rutherford never even reached the big leagues. With the Kenny Williams/Rick Hahn braintrust out of the way, we’ll see if the Yankees can continue their habit on coming out on the better end of these deals.