Extending Tim Anderson: Why The White Sox Must Act Quickly

Tim Anderson wants to stay in Chicago. He made that clear when talking to Scott Merkin of MLB.com, saying that he's "so comfortable" on the South Side and hopeful of getting another deal done to remain in Chicago long-term.

"I have a lot of things that are going on with kids and just family. Being comfortable is huge for me," the 29-year-old shortstop told Merkin. "No, I'm not promoting 'pay me.' It's just that's what's really going on. Everybody knows I want to be here. It's no secret."

This is reassuring to hear for fans. Anderson left some wondering if he wanted out after liking a Tweet this offseason that read, "I've seen Frank Thomas wear a different uniform. I know TA will eventually as well." The Tweet has since been unliked, but it is easy to see where Anderson is coming from. The White Sox massively underachieved and were the laughingstock of the AL Central.

Not only should Anderson's comments make fans feel good, but they should also be a signal to the front office as well. Anderson is under contract until 2023 with a club option in 2024 that will almost certainly get picked up. He will only cost the White Sox $12.5 million in 2023 and $14 million in 2024.

However, now would be the time to extend the two-time All-Star. Rick Hahn has been the master of extending players early and often. He locked up Eloy Jimenez and Luis Robert before they had even stepped on an MLB field. He also extended Tim Anderson, Yoan Moncada, Lucas Giolito, and Dylan Cease very early in their White Sox tenures.

The 2019 batting champion has hit a combined .318 over 374 games since 2019. Anderson has also given fans two of the more memorable walk-offs in recent history. The first with his bat flip to end the game in extra innings against the Tigers, and the second coming in the first-ever Field of Dreams Game after sending the ball into the cornfields.

Despite taking a step back in 2022, he still batted .301 and landed on the MLB's Top-100 list. A nagging groin injury and a tear of the sagittal band on his left middle finger cost hampered his production. It's his second season in a row cracking the top 100. However, he did drop from No. 31 before the start of last season to No.72. Coming off a down season is the perfect time to start negotiations in the hopes of getting a more team-friendly deal.

Like every player, Anderson has his shortcoming. His defense still needs vast improvements. His interviews are bland and, at times, hard to understand. Often his cryptic tweets leave readers scratching their heads.

But with his shortcomings, the White Sox would be wise to offer him an extension. Jose Abreu was the face of the franchise for nearly a decade, and even though his production far outweighed Anderson, he never thrust the White Sox into the national headlines. Anderson has made the White Sox relevant, cool, and before the start of 2022, fun to watch.

His bat-flipping in antics in 2019 put a team with a losing record at the forefront of the national baseball conversation. Anderson has also been a cover athlete for Sports Illustrated and RBI Baseball. He is one of the faces of baseball, and losing him will cost the White Sox not only on the diamond but also in marketing revenue.

They will not find a cheaper alternative on the open market. In the past few off-seasons, infielders have record deals. Corey Seager inked a $325 million contract with the Rangers. Manny Machado recently agreed to a $350 million deal with the Padres, and Trea Turner got $300 million from the Phillies. Xander Bogaerts also got $280 million from the Padres, while Anthony Rendon got $245 from the Angels a few years back.

Tim Anderson may not be of the same caliber as these players yet, but he is close. If he hits the open market, a team will overpay for his services. The White Sox have also shown they are unwilling to pay top dollar to overpay for one of these high-priced talents.

Anderson would be 31 in 2024, when he is expected to hit free agency. That is the same age as Marcus Semien when he signed a $175 million deal. That would easily surpass any contract that the White Sox have handed out. Andrew Benintendi currently owns the richest agreement at $75 million. The White Sox will likely have to hand out a $100 million deal to retain Anderson. But the longer they wait, the more expensive he will become.

Furthermore, the White Sox still have a hole at second base. Colsen Montgomery, who is seen as the White Sox future shortstop, can easily be moved over to second base to fill that void. He could also play third base once Yoan Moncada's contract expires. It would be no contest if you had to pick between paying Moncada or Anderson.