3 tiers of contract extensions the St. Louis Cardinals should prioritize right now

Tier #1 - Sign them now before the price goes through the roof

Masyn Winn and Ivan Herrera

Two players who won't hit free agency until 2030 and have one more offseason before hitting arbitration, Masyn Winn and Ivan Herrera, are in the prime spots of their careers to ink long-term extensions, should they be interested in achieving that long-term security.

Extensions with budding stars are not as simple as we may make it sound on social media or blog posts. If Winn, Herrera, or their agents decide that they want to bet on themselves and play it year by year in hopes of cashing in big time when they hit free agency, the only thing the Cardinals could do is hope an offer they make changes their mind. But I would guess in the case of both players, a long-term extension that buys out a few years of free agency is something they would be open to, if the price is right.

Neither guy should be getting some crazy Bobby Witt Jr. or Julio Rodriguez extension that is north of $300 million, but in order to lock them down beyond their current team control, the number will likely be well north of $100 million. Frankly, both guys are worth it.

Winn, in his sophomore campaign with the club, has taken a massive step forward with his bat and refined his defense even further, even after finishing as a Gold Glove finalist in his rookie year. Winn is slashing .278/.357/.438 in 186 plate appearances in 2025, posting a 125 wRC+, which is 48th in all of baseball and fifth among all shortstops this year, ahead of names like Witt Jr., Trea Turner, Francisco Lindor, Gunnar Henderson, Mookie Betts, and Elly De La Cruz. Is Winn better than those shortstops? I wouldn't say that right now, but it just goes to show you the kind of year he is having at the plate right now.

Winn is on pace for a 6+ fWAR season this year, an incredible feat by any player, let alone one as young as Winn. For context, that would have been fourth among all shortstops in 2024 and top 10 in all of baseball among position players. If Winn even just settles in as a 20% above league average bat for his career with the elite defense he plays, he's one of the most valuable players in today's game.

That makes the floor for Winn very high as well. In his first full season as a pro last year, Winn posted a 3.6 fWAR season, 43rd in all of baseball. He was barely an above-league-average hitter, so the more upside he shows at the plate, the more value he adds to his game. We are seeing that play out in real time this year.

For Ivan Herrera, a potential extension is 100% focused on what he can provide the Cardinals offensively for years to come, and they can figure out what that means defensively in the future.

So far this year, Herrera is slashing .358/.438/.630 with an insane 194 wRC+ to show for it. Mostly logging time as the Cardinals' designated hitter, his bat is producing like one of the best in all of baseball, and the Cardinals need to focus on helping him continue to tap into that production and then figuring out how to keep him in St. Louis for a very long time.

Everything in Herrera's profile points to him being an elite hitter moving forward, and this production is not just coming out of nowhere. Sure, he wasn't a top 5 hitter in baseball good the last few years, but since debuting in 2022, he has the 21st highest wRC+ (135) in all of baseball. All Herrera has done is hit at every minor league level and in the big leagues, and I expect that to be the case moving forward.

If so, the Cardinals have to get him locked up quickly. In today's game, finding a bat as good as Herrera's would cost the Cardinals an insane amount of money in free agency, especially if he can do that as a catcher or provide defensive value at another position. The Cardinals have not been able to develop a middle-of-the-order bat for over a decade now, and Herrera looks to be their long-awaited answer to that question.