What a fair extension for Brendan Donovan and the Cardinals could look like

The St. Louis Cardinals are facing a crucial decision this offseason regarding the future of Brendan Donovan. Will they trade him? Or will they build their new core with Donovan as a part of it?

So many teams around the league are interested in acquiring Donovan, but recent reporting indicates that unless the Cardinals are blown away by an offer, they'll likely pass on moving him. If they don't trade him, they need to extend him, as letting his team control waste away and losing him in free agency would be an awful decision.

So, what if the Cardinals do keep Donovan? What could an extension look like?

Extending Brendan Donovan would be expensive, but worth it if the Cardinals get creative

I gotta be honest, the Cardinals missed the boat on not extending Brendan Donovan last offseason. Like, big time. With three years of club control remaining and his All-Star season looming, the Cardinals should have had the foresight to extend him then, likely getting a better deal on his contract than they will now.

Unfortunately, they stayed frozen in John Mozeliak's final winter, and now if they did bring back Donovan on a long-term deal, it'll cost them quite a bit.

According to FanGraphs, Donovan has been worth $20+ million per year in his career thus far. In 2022, Donovan's rookie season, he posted $20.7 million of value for St. Louis. In 2023, in just 95 games, he was worth approximately $12.5 million. In 2024, he went all the way up to $25.4 million, and in 2025, he was worth $22.8 million while missing a chunk of games and playing the whole summer with turf toe.

Believe it or not, in FanGraphs' model, Donovan has never been a positive defensive player, and while we know he brings real value to the table on that side of the game, that means his bat alone has been giving him that kind of value for St. Louis. Many believe he still has a bit more in his bat that he can unlock, and honestly, he should be able to continue to be a versatile defender for a number of years.

Put all of this together, and once Donovan hits free agency, you're likely looking at a player set to make over $20 million per year, with the exact AAV likely being contingent on how long that deal is.

If the Cardinals were to extend him before his arbitration number locks in, they would be looking at covering two arbitration years plus any years of free agency they buy out, so they could structure the deal in such a way that he gets paid above his arbitration projections in 2026 and 2027 in order to save money on the back end of the deal.

If Donovan hits the open market following the 2027 season, playing the way he has thus far in his career, I'll say he would get about $23 million per year over three years, bringing him to his age-33 season. Josh Naylor, who has been worth an average of $19.62 million per year in his four full big league seasons and is a first base/DH-only player, just got $18.5 million over five years. With Donovan being worth more per year and having even more upside, being able to play second base, third base, and the corner outfield spots, he could beat Naylor's AAV by quite a bit on a shorter deal, in my opinion.

Now, if the Cardinals were to extend Donovan now, they would be buying out his estimated $5.4 million arbitration number this year and something next year in the range of $8 million, so that alone would knock the AAV on an extension down. In my eyes, a five-year extension for Donovan that covers his final two years of team control plus three free agent years would be ideal for the Cardinals.

With that being said, here's what I think a fair extension could look like for Donovan:

Total deal: Five years, $83 million ($16.6 million AAV)
Year-to-year breakdown:
2026 - $12m
2027 - $14m
2028 - $19m
2029 - $19m
2030 - $19m

The Cardinals can obviously get more creative by adding buyouts, option years, flattening the rate out to get more savings on the back end, or even front-loading the deal so they have him on a true bargain during his free agent years. If Donovan continues to be the player he has been so far, he'll be underpaid every year of this deal, but if he takes another step forward, he'll be producing closer to $30 million in value each year while being paid only part of that total.

I actually think this is probably a very team-friendly deal if Donovan were to take it. With him being so close to free agency, he could bet on himself here and try to be worth even more by the time his club control ends. But given his injury history and a potential lockout coming, maybe locking in the money now makes more sense.

Again, none of his fWAR value even factors in the value Donovan brings defensively; in fact, it penalizes him in defensive rating, and it definitely doesn't account for the value he brings to a clubhouse. It is really not hard to see how Donovan could be a great value for the Cardinals on a long-term extension, should they choose to go that route.

In all likelihood, the Cardinals will be trading Donovan in the coming weeks, which is a major loss for the organization. It does sound like he will be fetching a haul for the Cardinals, which is definitely a plus, but if I had my way, I'd be working on a long-term deal with Donovan right now.