CHICAGO -- As weird as it must have been for Rick Hahn to watch Chris Sale pitch against the White Sox, this was late May, not late October.
How awkward would it be for the man who traded Sale to watch him lead the Red Sox to the World Series? Or would it even be awkward at all?
"There's positives from that on a couple of different levels,'' said Hahn, the White Sox senior vice president and GM, on Tuesday. "First, as an organization, regardless of what uniform Chris is pitching in, our amateur scouts, our player development people and our Major League coaches, each had a little bit of a hand in helping Chris reach his potential, [and they] should feel some pride. Secondly, as a fan of the game, someone with a great deal of respect for Chris -- I consider him a friend -- I'd be happy for him to showcase those talents on a national stage.''
On the other hand ….
"That said,'' Hahn said, finishing his thought, "certainly it would be bittersweet in some ways to see that happen, knowing we weren't able to get it done while he was in our uniform.''
The White Sox never won more than 88 games in Sale's seven seasons on the South Side, and fell short of 80 in each of his last four. Sale was often dominant -- losing a perfect game to a seventh-inning single by Mike Trout in 2013; striking out 15 Cubs in '15. Yet, there wasn't a signature moment that ended with him triumphant on the mound.
It was time to give him a fresh start elsewhere, so Hahn did just that, in a trade with Boston that may ultimately look like one of the best kinds, benefiting both teams.
Hahn restocked the organizational cupboards in a four-for-one trade that included two of the Red Sox top three prospects (infielder Yoan Moncada and right-hander Michael Kopech). It was the biggest in a series of moves that have given the White Sox a highly regarded farm system (No. 3 according to MLBPipeline), after years when the supply of Minor League talent couldn't meet the team's needs.
He's not about to stop now.
While the American League Central standings show the White Sox are competitive, they are positioned to be baseball's biggest sellers this summer. They could deal one-quarter of their roster between now and the July 31 non-waiver Trade Deadline, and the deal they'd most like to make involves the guy who faced Sale on Tuesday night, lefty Jose Quintana.
Unfortunately for the White Sox, he's pitching like a guy who doesn't want to go anywhere.
The Red Sox scored seven runs off Quintana in only 2 2/3 innings on Tuesday, with two homers by No. 9 hitter Deven Marrero. It continued a puzzling stretch of ineffectiveness for the guy who was a highly effective wing man for Sale over the past five seasons.
Quintana is under control with a team-friendly contract (through 2020, including club options), like Sale, but heads into June with a 2-7 record and 5.60 ERA. Teams like Houston and Pittsburgh look smart for not meeting the White Sox high asking price for him last winter, but Quintana could still put himself into play with strong work in June, assuming no health issues.
Hahn will probably never again make a trade as gut-wrenching as the one that sent Sale to the Red Sox.
"You never feel a great deal of excitement trading a player as talented as Chris,'' Hahn said. "Obviously, he's picked up in Boston right where he left off with us, to no one's surprise.''
"It was the first clear statement about how serious we were about this renewed commitment to our future, and building something long term and sustainable, instead of trying to patchwork things [together] on the fly,'' Hahn said. "I think it was important in terms of a big step forward for what were trying to accomplish, and also important in terms of a declaration about what we were going to be about around here for the coming years.''
Hahn's dream is to build a deep, complete roster and back it with a young starting rotation that resembles the staff that took the Mets to the National League Championship Series in 2015. The White Sox have assembled an intriguing cast, with Carlos Rodon (currently on the disabled list with biceps bursitis) and prospects like Kopech, Carson Fulmer, Lucas Giolito, Reynaldo Lopez, Dane Dunning, Alec Hansen and Spencer Adams.
Meanwhile, the Red Sox chase an extended October run behind a front three that features Sale, Rick Porcello and David Price.
Sale will have a lot of nights better than this one, when he was handed 4-0 and 7-3 leads and had to fight his hardest just to get through five innings. His ERA jumped from 2.34 to 2.77, as his old teammates got to him for six runs (five earned) and 10 hits (the most dramatic of which was a Jose Abreu single on a changeup after Sale had thrown a series of fastballs at 97, 97, 98, 98, 98 and 97).
The bottom line for Sale was nine strikeouts and enough stuff to protect the lead when he was scuffling.
You can bet the Red Sox would take a result just like this in October.
So, too, would Sale, who has never pitched in the postseason. It took a win-win trade to put him in position to get his first taste.
Phil Rogers is a national columnist for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.