It is no secret that Colson Montgomery is good at baseball. MLB Pipeline recently ranked him as the ninth-best prospect in the sport, and he is by far the best prospect in the White Sox organization. He has repeatedly drawn comparisons to Corey Seager and has lived up to that comp, destroying every Minor League level he has been at thus far. Montgomery looks to be a future star and the face of the franchise once Luis Robert Jr. is inevitably traded. Montgomery will be on the South Side for a long time regardless, but if he is as good as we all think he will be, it might be in the White Sox’s best interests to ink him to a long-term contract extension now. Doing so would lock in his yearly salaries and give the Sox an extra season or two of his services when he should hypothetically be in his prime.
Contract Extensions: A Common Practice
The idea of signing players early in their MLB careers is not new, nor exclusively a White Sox one. Just this offseason alone, the Brewers gave a massive contract extension to their top prospect, Jackson Chourio, before he has ever played in an MLB game. The Tigers did something similar with Colt Keith, one of their better prospects. These contract extensions typically involve the team buying out arbitration years of young players. In other words, teams pay young players more money in the early stages of their careers than they would receive under normal circumstances had they not signed a contract extension. In exchange, the team typically adds a couple of team options onto the back end of the contract when the player is hypothetically in their prime. There is risk for both sides in a deal like this. The team might be on the hook for a significant amount of dead money if the player does not pan out. From the player’s perspective, signing a contract early in their career might cost them significant money if they become stars. This overall contract structure could hypothetically apply to Montgomery should he be interested.
White Sox History With Contract Extensions
I briefly mentioned this idea on Twitter and got many replies for both arguments. Most Sox fans were against it, which is a fair perspective. After all, the White Sox’s history in handing out extensions of this nature has been questionable at best. They gave a massive contract to Eloy Jiménez in March of 2019 before he ever appeared in an MLB game, and that has not panned out as we had hoped. They also gave a contract extension to Yoán Moncada early into his MLB career that has yet to pay dividends thus far. Tim Anderson’s contract extension was aging great until it wasn’t. Same for Aaron Bummer.
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Yet, on the flip side, the White Sox also took this approach with Luis Robert Jr., and it has paid off big time. They gave him a six-year contract with two team options in January of 2020 before he had ever played in an MLB game. While injuries have held him back to an extent, Robert Jr. finally put everything together in 2023 and had the best season of his career. He is now one of the most valuable assets in the sport, and his performance on the field is only part of the reason why. While Robert Jr. is an All-Star caliber player, his contract significantly inflates his value. Robert Jr. has four more seasons left on his deal at a salary that is a steal for a player of his caliber because of the contract he signed in 2020. The White Sox now have a star on a bargain contract or a potential elite trade chip that will fetch a massive haul of prospects if they decide to trade him at some point. It is also worth noting that the White Sox used this same process for the trio of Chris Sale, José Quintana, and Adam Eaton nearly a decade ago. All three of those players signed long-term contracts relatively early into their careers. They all ended up being extremely team-friendly contracts, which is why all three of them were traded for massive prospect hauls (at the time) in 2016 and 2017, when the White Sox began their initial rebuild.
From Colson’s Perspective
In the case of Colson Montgomery, it is unclear if he would even be open to signing a contract of this nature, and these discussions could also be premature as he has yet to reach the AAA level. Next year might be a better time to have this conversation. But this concept of trying to lock up talented young players long-term applies universally to all who come up through the White Sox system, not just Montgomery. The goal should always be to keep players with star potential around for as long as possible, especially for the White Sox, who do not pay for star-free agents under Jerry Reinsdorf’s ownership. There is risk involved for both parties in contract extensions like this one, but they should not abandon this concept entirely because it didn’t pay dividends in the cases of Eloy Jiménez and Yoán Moncada.