Today in White Sox History: February 19

The South Siders fall short of signing Manny — and do so in utterly embarrassing fashion

2019

In a bonafide shocker, Manny Machado spurns the White Sox and signs a 10-year, $300 million deal with the San Diego Padres — the biggest in U.S. professional sports history at the time.

The White Sox were considered the easy front-runner, and had offered a supposed “best deal.”

“I’m wearing my shades, so you can’t see the shock in my eyes,” White Sox executive VP Ken Williams said after the announcement. “Very surprised. There are a few other words you could put on that, but still in a little bit of disbelief ... I honestly believe we had the best offer on the table.”

As much as he was lambasted for falling short of delivering Machado to the White Sox, Williams wasn’t completely wrong in his assessment. The White Sox’s final offer to Machado was said to be eight years and $250 million, with club options (based on plate appearances) that would have pushed the total value to $320 million.

However, the White Sox did not provide a seeming no-brainer: a player opt-out. San Diego did include a player option after five seasons, which was instrumental in delivering Machado. (In recent days, Machado has indicated that yes, in fact, he will exercise his opt-out after the 2023 season.)

More embarrassing was that the White Sox had already acquired Machado compadres Jon Jay (free agency) and Yonder Alonzo (trade with Cleveland), but their “friends and family plan” failed. Worse, the two players ended up endorsing Machado’s decision to sign with San Diego instead of becoming their teammate on the White Sox.

To date, Machado has earned $78 million in San Diego, while putting up 17.6 WAR. At $4.4 million per WAR, Machado has proven a bargain, a fact that’s utterly amazing given the fact that he was signed as the very top of the market, to a record-breaking deal.