The White Sox Made a Major Mistake by Sitting Out the Trade Deadline

It was August 12 and the White Sox had a day off on the field, and their off-the-field plans served as a visceral reminder they absolutely, positively should have gone all-in at the trade deadline.

What happened? The Sox hosted a Zoom news conference for Tim Anderson.

Ostensibly designed for Anderson to announce his retirement (and, somewhat surprisingly, bare what thankfully appears to be a less tormented soul), his announcement was a convenient news peg for the Zoom’s real purpose: To kickstart the team’s marketing plan to wear the black Southside jerseys one last time on Sept. 17.

To reiterate: The whole thing started with the team planning the night. Then they called Anderson, who never would have reached out to reporters to discuss retirement or anything else, to ask if he’d throw out the first pitch prior to that Thursday night (potential) showdown with the Detroit Tigers.

One thing led to another and, shazam, marketing synergy achieved! Everyone in the Rate Field executive suites surely is pumped about all the “earned media” they’re getting.

To be fair: When you consider “TA” is the White Sox most closely identified with those iconic City Connect jerseys -- and because he’s now officially done -- Sept. 17 provides Anderson and Sox fans a chance to share one last powerful moment together.

Not on the level of the terrifically done Ozzie Guillen jersey retirement ceremony a few nights before the Anderson bit came together, but still something that’s pure South Side.

But the fact this happens so soon after Anderson’s reign -- only seven years since he led the AL in batting average, five since he hit the walk-off homer into the Field of Dreams cornfields and four since his last All-Star Game – is a reminder that future greatness is promised to no one and no team.

Anderson was 28 years and two months old when he jacked that homer into the corn. The Sox were well on their way to the Central Division crown with Garrett Crochet (22), Andrew Vaughn (23), Luis Robert Jr. (24), Eloy Jimenez (24), Dylan Cease (25), Michael Kopech (25), Yoan Moncada (26), Lucas Giolito (27) and Carlos Rodon (28) all riding shotgun in various stages of excellence -- anticipated or otherwise.

But that team didn’t win jack. Lost 3-1 in the ALDS to the Houston Astros, in case you forgot. Just two years later, right about the time Rick Hahn and Kenny Williams got whacked in favor of Chris Getz becoming the general manager, Anderson was a negative-WAR player in his final days with the team. Moncada had worn out his welcome, too. Kopech was leading the AL in walks. Rodon was gone, Crochet threw 12 innings, Vaughn and Eloy were the epitome of mediocrity. Cease would be dealt in the offseason for four guys who have combined for .8 of a win in a Sox uniform (per WAR).

On the plus side, Robert earned his lone All-Star Game nod in 2023 while stacking up 38 homers, 36 doubles and 20 steals. He was a superstar and, of course, he was going to stay a superstar for the South Side. Of course, everyone knows how he has fared since.

Simply put, teams must strike when they’re in the White Sox’s exalted position.

They may be a piddling six games over .500 heading into the week, but the American League never has been so weak. If MLB canceled the rest of the regular season today and decided to go straight to the postseason, the White Sox would have the No. 2 seed and a bye to the American League Divisional Round.

In this unbelievably fortunate situation, it absolutely would have been worth sacrificing two or three legitimate prospects to boost the chances of besting the Rays, Red Sox or whomever else in the AL.

It’s lovely that 20-year-old Caleb Bonemer is raking at Double-A Birmingham. It’s awesome they just spent a bunch of money to draft Roch Cholowsky and Landon Thome and Josh Prosek. It’s beautiful that Hagen Smith, the No. 5 overall pick in 2024, won his MLB debut this month. Someday we’ll laugh instead of cry that he walked four guys in that two-inning stint.

But it is absolute malpractice to presume the White Sox will be in the same spot (or better) in 2027, 2028, 2029 and beyond just because they have a lot of prospects whose names we know – and because Murakami, Vargas, Montgomery (B), Montgomery (C), Antonacci, Teel, Smith, Schultz, Taylor and others are in their mid-20s.

To quote one famous Chicagoan, architect Daniel Burnham: “Make no little plans.” To quote another, Ferris Bueller: “Life moves pretty fast. If you don’t stop and look around every once in a while, you could miss it.”

Somewhere on a concrete slab near Grant Park, Hahn continues to look around in vain for those multiple World Series parades he projected. Maybe he won’t be joined on that curb by Getz. Time will tell.

But when you’re the No. 2 seed in the league, you make the damn deals to become No. 1 in October.