Over the past few seasons, we’ve discussed which current St. Louis Cardinals players should be signed to extensions. While manager Oliver Marmol signed an agreement during Spring Training and Tommy Edman had his remaining arbitration years bought out this winter, it has been a while since a Cardinal received a long-term extension before entering free agency.

Paul DeJong just inked a six-year, $26 million contract extension with the club following an excellent debut season. While the arrangement did not work out in the end, it was a unique attempt by St. Louis to lock on a young core member of their club on a team-friendly contract.

While there are other players we might discuss that the Cardinals should consider extending, Brendan Donovan appears to be the most obvious possibility for a contract in the near future.

I recently wrote about how Brendan Donovan has not only been the club’s MVP this season from a position player standpoint but he’s proven to be the straw that stirs their drink as an offense ever since he debuted in 2022.

Donovan is seventh on the squad in fWAR (5.6) in only 299 games, and third with 121 wRC+. He’s already won one utility Gold Glove, and he’s making a strong case for another this year with his outstanding defense in left field and ongoing flexibility across the diamond and outfield. Donovan is a fantastic hitter who also plays great defense at practically every position, making him a player you want to keep around for a long time.

Donovan is not only a valuable player on the field, but also a strong leader in the Cardinals’ clubhouse. He should be a key figure in the team’s future success. While other Cardinals players have bigger ceilings as baseball players, Donovan is toward the top of the list in terms of who is most important to this new core.

Donovan will become arbitration-eligible for the first time after the 2024 season and will be available for free agency after the 2027 season. Donovan’s compensation will rise gradually over the next few years, and he should be able to sign a lucrative contract once he reaches free agency after turning 30.

The Cardinals could simply play the arbitration game with Donovan for the next few years, but I believe both sides are perfectly positioned to reach an agreement on a long-term extension that would provide Donovan with long-term security while also saving the Cardinals money in the future.

Matt Carpenter, a guy Donovan has been likened to multiple times in recent years, had a similar agreement from the Cardinals early in his career. While fans tend to recall his second extension, which did not age well, Carpenter’s first extension was a true steal for St. Louis. Prior to the 2014 season, Carpenter signed a six-year, $52 million contract extension with the club, which included the purchase of his remaining team control as well as certain free agent years.

The Cubs’ second baseman Nico Hoerner recently got a three-year, $35 million contract with Chicago after settling for $2.5 million in his first year of arbitration. This may provide insight into Donovan’s potential market. The Cubs were able to buy out Hoerner’s final two years of arbitration while also covering one year of his free agent eligibility. This was before Hoerner won his first Gold Glove, and he had been a league-average hitter up until that point.

Donovan will have his first crack at arbitration this offseason, so you could probably get him to a slightly lower AAV because of that, but if he were to have multiple years of free agency bought out, that number probably gets close to the $11.5 million AAV that Hoener received.

I think a deal spanning about six years with an AAV of around $11 million could get the job done for both sides. For St. Louis, they not only lock in the certainty of Donovan’s number for the next six seasons, but they are also able to extend Donovan into three of his free agency years, delaying the year he hits the open market from following the 2027 season to after the 2030 season.

Using the Hoerner contract as a comparison, Hoerner only made $2.5 million in his first year of arbitration before seeing his salary jump to $11.5 million in his last two arbitration years and then $12 million in what would have been his first year of free agency. For Donovan, he could get an immediate pay bump in his first season of arbitration in this scenario but do so by giving the Cardinals a discount on two extra free agent years compared to Hoener.

While I won’t try and predict the official breakdown of a deal, the Cardinals could look to backload the deal a bit, giving Donovan smaller pay bumps early on in this extension compared to potential arbitration numbers, and then receieve similar discounts on the free agent years. Or they could explore a consistent AAV where Donovan gets a major pay bump early in the deal but the Cardinals pay him significantly less than market value later on.

It’s also worth noting that before the season, The Athletic projected a potential Lars Nootbaar extension to be somewhere in the seven-year, $68 million range, so perhaps the Cardinals could get Donovan on a lower AAV, but I personally feel like his play this year has continued to raise his price tag.

Would you sign Donovan to a contract in the ballpark of six years, $66 million? I would. It wouldn’t shock me to see St. Louis get that number a bit lower as well, or to see Donovan want more than that. But if I’m the Cardinals, I’m trying my best to get Donovan locked up long-term, rather than having to pay market value when he hits free agency.