Both Chicago Cubs and White Sox fans are talkative about the San Diego Padres and their recent trades to better their roster this week. On Sunday night, the Padres acquired Cy Young pitcher Blake Snell from the Tampa Bay Ray and later trading for Cubs' pitcher Yu Darvish a day later. San Diego's rebuild and championship window has been similar to that of the White Sox's rebuild, but have made bolder moves that the White Sox.

The White Sox Continue To Pass On The Big Move

When the White Sox began their rebuild in December of 2016, they made significant trades to replenish their farm system that lacked quality prospects. By trading All-Star pitcher Chris Sale and outfielder Adam Eaton, the team acquired prospects Yoan Moncada, Michael Kopech, Lucas Giolito, Reynaldo Lopez, and Dane Dunning. General manager Rick Hahn continued to make trades, international signings, and quality draft selections to build one of the youngest and talented cores in baseball. Now, with all those young players entering their prime, Hahn has failed to add the best available talent via trades or free-agent signings to make the team a legitimate World Series contender.

It began in the offseason between the 2018 and 2019 seasons, where the White Sox had the lowest payroll in baseball and were able to spend on the best free agent available. Chicago could have either signed All-Start third baseman Manny Machado or outfielder Bryce Harper. Chicago was the favorite to sign Machado until San Diego stepped in and guaranteed a tenth and final year of a contract where the White Sox wouldn't. The White Sox's failure to guarantee a final season, in turn, led to the All-Star signing with the Padres over the White Sox.

Although Hahn made up for the Machado debacle by signing Yasmani Grandal and Dallas Keuchel a year later, the White Sox continue to pass on signing the best free agents available. The organization continues to state they are in a "win now" mode but fail to prove it. The signings and trades made this offseason continue to demonstrate how the team is falling short of the message fans and the media are being told.

Chicago's two most prominent needs this offseason have been starting pitching and adding a starting right fielder. While outfielder George Springer and pitcher Trevor Bauer are the two best free agents available, the White Sox filled their needs by signing outfielder Adam Eaton and trading for pitcher Lance Lynn. It is frustrating because signing either Springer or Bauer would make Chicago a more formidably playoff contender, but the team does not appear interested in signing either player.

San Diego Continues To Thrive Where The Chicago Fails

Unfortunately, White Sox have skirted making the best move possible as the Padres have firmly jumped when the opportunity has presented itself. Although San Diego is a smaller market than Chicago, it did not stop them from signing Machado to a 300 million dollar contract. Like the White Sox, the Padres have spent several years restocking their minor league system with quality prospects, but unlike the White Sox, they have traded those prospects away from some of the best pitchers in baseball.

In the last six months, San Diego has acquired Snell, Darvish, and pitcher Mike Clevinger. Although Clevinger will miss the 2021 season due to Tommy John surgery, the Padres have sacrificed their future to try and win the World Series in the next few seasons. The White Sox, on the other hand, have yet to a premium that puts them in the best position to win now.

San Diego has now positioned themselves to be a creditable threat to win the National League West Division and worthy challengers to the Los Angeles Dodgers. Last season, the Padres were eliminated by the Dodgers in the National League Divisional Series in three games due to their lacked starting pitching. They have addressed their weakness by adding two of the best pitchers in all of baseball in Darvish and Snell.

The White Sox At Some Point Need To Make the Big Move

The White Sox, with the additions of Lynn and Eaton, are a better team than they were last season. The issue at hand is that the White Sox need to make the blockbuster signing or trade more so for culture change, rather than for an on-field purpose. In the last three years, Hahn and his organization has a golden opportunity to make those moves but have always fallen short due to something not lining up. Whether it has been not wanting to part with a prospect, spending money, or guarantying final years instead of options, there is something that always gets in the way. With the Padres' ability to make moves without hesitation, the hesitation and restraint that holds the White sox back will catch up with them sooner or later. Premium free agents won't take the Chicago organization seriously while opposing teams will capitalize on making blockbuster trades that the White Sox appear hesitant to make. Both teams could face each other in a future World Series, where the moves the Padres have made will make the difference.