The 2021 Chicago White Sox season ended in disappointment on Tuesday as the team was eliminated from the MLB playoffs by the Houston Astros. During the Astros’ 3-1 Divisional Series victory, many of Chicago’s flaws were exposed, as it is now apparent what the franchise will need to do in the offseason to improve. Unlike prior seasons, Chicago’s ownership cannot afford half-measures when it comes to adding talent to a team expected to compete for a World series the next few seasons.

Season is over for the Chicago White Sox.

They get eliminated in the ALDS by the Houston Astros.

— Daniel Greenberg (@ChiSportUpdates) October 12, 2021

White Sox Have Made Additions During Prior Off Seasons, But On Their Terms

The White Sox rebuild that started in December of 2016 was twofold as the plan for general manager Rick Hahn was to trade Chicago’s veteran talent for top-level prospects while garnering top Draft selections with poor records. Following two years of uncompetitive baseball, the White Sox would then add premium free agents with money saved by having extremely low payroll. Chicago was saving money to spend during free agency following the 2018 season when All-Stars Manny Machado and Bryce Harper were available.

Despite having the most money to spend and having the lowest payroll in all of baseball at the time, the White Sox would miss on signing both free agents leading to extreme criticism from fans, along with local and national media. Machado would sign with the San Diego Padres, while Harper would sign with the Philadelphia Phillies. White Sox owner Jerry Reinsdorf was viewed as being the main factor as to why Chicago was outbid by other teams in relation to both free agents, as the owner appeared reluctant on signing players to large record-breaking contracts.

Why this is a PR Disaster for the Sox:

You have never spent more than $68M on a player before.

You told fans this time would be different, that the money would be there.

You did it so effectively the fans believed you.

You failed to come through.

They won't believe again.

— Rick Gregg (@rickgregg) February 19, 2019

Many White Sox fans became skeptical of the team’s commitment to rebuilding and desire to win a championship as an inability to spend money during free agency became apparent. Hahn assured Chicago fans that the money that was supposed to be used for Machado and Harper would be spent one way or another. In 2019 and 2020, the White Sox would spend money on quality free agents, including Yasmani Grandal, Dallas Keuchel, and Liam Hendriks. Although not the best free agents available, Grandal, Keuchel, and Hendriks were the best available players at their position.

November 21st: White Sox sign Yasmani Grandal

December 21st: White Sox sign Dallas Keuchel

Can’t wait to see what the Sox have planned for us on January 21st!

— Mike (@ChiSoxFanMike) December 22, 2019

Another tactic utilized by the White Sox front office has been to substitute a free agent signing with a call-up of one of their top minor league prospects. In 2019, Chicago called up slugger Eloy Jimenez to appease the fans upset about failure to sign Machado or Harper. A year later, the White Sox would call up their number one prospect in centerfielder Luis Robert while calling up outfielder Andrew Vaughn this season to fill the void by not signing a free agent outfielder or designated hitter.

Can confirm the Luis Robert contract extension with the White Sox. 6 years, $50 million, plus two option years. He also passed his physical.

— Chuck Garfien (@ChuckGarfien) January 2, 2020

The issue with the prospect callup tactic is that the White Sox will not have a top prospect to call up before the start of the 2022 season. The lack of a readied prospect will now force the team to sign a premium free agent during the offseason. Furthermore, for Chicago to compete for a World Series in 2022 and 2023, the team will need proven veteran talent and not players that will need a few years to develop.

The Impending Offseason Will Enable The White Sox To Finally Spend on Top-Tier Free Agents

During free agency following the end of the 2021 World Series, the White Sox will need to fill three specific needs, including adding a right-fielder, starting pitcher, and a second baseman. Unlike in prior off-seasons, the White Sox do not need to spend money on the best free agent available but can still sign available premium talent. Although Leury Garcia and Cesar Hernandez provided quality depth for Chicago in 2021, it was apparent that either of the two can’t be counted on as proven starters throughout an entire season.

The White Sox will need to add a starting pitcher to their rotation for the 2022 season as Carlos Rodon will be a free agent during the upcoming offseason, and Keuchel’s career appears to be on a downward trend after posting a 5.28 ERA and failing to make the post-season roster. Chicago’s starting rotation featured two left-handed starters in 2021, could now be without one in 2022. One free-agent option for the White Sox could be 30-year old Steven Matz, who posted a 3.82 ERA with the Toronto Blue Jays in 2021.

Steven Matz finishes the season with a 3.76 ERA over 150 2/3 innings.

A fantastic finish to a solid season. Matz has been truly valuable to this rotation and set himself up nicely for free agency. #BlueJays

— Keegan Matheson (@KeeganMatheson) October 2, 2021

Although Rodon had a terrific 2021 season, his injury-prone history made him unreliable in the second half of this season and his lone postseason start during Tuesday’s ALDS Game four loss. If the White Sox move on from both their starting left-handed pitchers, Matz would be a proven option as he has averaged close to 30 starts the last three full seasons.

Two prominent position players the White Sox need to target during free agency are outfielder Nick Castellanos and second baseman, Marcus Semien. Castellanos would give Chicago a proven right-fielder who is capable of hitting 40 home runs. Semien would provide the White Sox with a proven infielder capable of playing third base, shortstop, and second base. Both players hit over 40 home runs each in 2021, and if added, would give the White Sox the best lineup in all of baseball.

OH MY. MARCUS SEMIEN WALK-OFF HOME RUN. 🤯@BlueJays | #BlueJaysOnSN pic.twitter.com/w5m74EhVWi

— Sportsnet (@Sportsnet) September 4, 2021

What potentially works in the White Sox favor if the team were to target either of the three free agents is that they wouldn’t be the most expensive free agents on the market. Carlos Correa, Corey Seager, Javier Baez, and Trevor Story are projected to be the most expensive free agents of the 2021 offseason. These free agents could enable the White Sox to work on more affordable but still expensive contracts with either Castellanos or Semien.

Nick Castellanos with an Opening Day home run!

Stream the game: https://t.co/F2yi8O9ByB pic.twitter.com/006suDBSEB

— Cubs Talk (@NBCSCubs) August 21, 2019

The White Sox will need to sign free agents to bolster their roster before the 2022 season as none of their prospects will put the team over the top to compete for a World Series. Chicago does not have a premium prospect to fall back on and call up if they do not wish to spend on a free agent. If the White Sox are serious about winning a World Series in the next few seasons, it will be up to Reinsdorf and Hahn to spend the money they have been reluctant to spend on premium free agents the last few off-seasons