This extension would be a win-win for the Cardinals and Ryan Helsley

If the St. Louis Cardinals are really holding onto Ryan Helsley this offseason, then it would be in the best interest of both parties to explore a win-win extension in the meantime.

With Helsley having one year of club control remaining before cashing in on his big payday, there is a world where the Cardinals can give Helsley a significant pay raise for 2025 and the long-term security he'd desire while not breaking the bank to quite the level that clubs like the New York Mets and Houston Astros have for star closes Edwin Diaz and Josh Hader.

There's been a lot of speculation lately regarding how much Helsley could command in free agency. Honestly, that number is difficult to pin down right now, as he still has one more year to increase or decrease his value, depending on both his performance and his health, as well as a shorter track record of dominance compared to the aforementioned closers.

Hader, even with a disastrous year in 2022 followed by more dominance in 2023, snagged a five-year, $95 million deal from the Astros in free agency last offseason. Diaz, who took the league by storm in 2022 but had an excellent career leading up to that point, received a five-year, $102 million deal with a club option for a sixth year at $17.25 million. Helsley could get close to those numbers if he has a dominant 2025 campaign, but cashing in this offseason would likely mean forgoing a bit of money to lock in 80% or more of what those guys got.

Let's take a moment to compare some of the career metrics of Diaz, Hader, and Helsley leading up to free agency. Again, it's quite apples to apples here with Helsley lacking that final season of production that those other names had since he's still a year away from free agency, but it at least gives us an idea of what their track record was at the negotiating table. I'll throw in Raisel Iglesias as well, who commanded a four-year, $58 million deal from the Angels after the 2021 season.

There are a few things working for and against Helsley when you compare these bodies of work. First, Helsley doesn't have the sheer number of games and innings that the others have on this list, which I think is both a bargaining chip and something teams can use against him. Fewer games and innings mean less wear and tear on his arm, which I think is a great thing, but he is already 30 years old entering 2025, meaning he'll be a year older than Hader was when he hit free agency and three years older than Diaz was.

His career ERA to that point is easily the second-best of the bunch and all of his rate stats could look even better if he adds one more dominant season to his resume prior to free agency, although, those numbers could also look less enticing if he takes a step back next year or runs into injuries.

Based on what we see here, and the risk-reward for both Helsley and the Cardinals to get a deal done now versus waiting until free agency, I think it's safe to say Helsley wouldn't get the $20 million or $19 million AAV that Diaz or Hader got in their deals, but he should surpass Iglesias' $14.5 million AAV, especially with Iglesias being a year older than Helsley was hitting free agency when he did.

Here is what a Ryan Helsley extension with the Cardinals could look like this offseason

Let's say that Helsley's market value right now is $17 million a year over the course of a four or five-year contract. It's not quite what Diaz and Hader were able to achieve due to their track record, but pretty dang close, especially since Helsley would be locking in his long-term deal a year before free agency and foregoing the risk of injury in 2025.

Helsley is set to make $6.9 million in arbitration this year. That's $10.1 million less than the market value we established. If the Cardinals extend Helsley before their arbitration process and instead give him a significant pay bump this year, they could cut some AAV off the latter years of the deal in the process.

I also want to look at this deal from the lens of what the Cardinals tend to like doing when they sign free agents or give extensions. With John Mozeliak in his final year and Michael Girsch being shifted into a new role with the front office, it is hard to know if they would keep their same patterns in place, but let's at least assume so for now.

• We know the Cardinals tend to like to backload contracts (see Willson Contreras, Sonny Gray, Steven Matz, etc.).
• There is also precedent here for them giving raises to players in arbitration or the final year of their deals to save money on the back end of the deal (see Tommy Edman and Miles Mikolas).
• We also know they like to include club options at the end of deals with buyouts, and that is a way to add guaranteed money to the deal while keeping the years leading up to the club option on a lower AAV.
• Lastly, we need to keep into account that they are still cutting payroll this year, so they likely want to keep the 2025 number (and potentially 2026) lower if possible, but they should have wiggle room to increase Helsley's salary after letting free agents walk and potentially still trading some money off their books.

With all of that being said, here is the extension I cooked up for Helsley and the Cardinals.

Year 1 (2025) - $12m
Year 2 (2026) - $13m
Year 3 (2027) - $15m
Year 4 (2028) - $15m
Year 5 (2029) - $15m
Year 6 (2030) - $17m (mutual option, $5m buyout)
Total: 5 years, $75 million (6 years, $92 million if mutual option is exercised)

How did I get to these numbers? Well, let me break down how it all came together.

1. First, took the $17 million AAV market value we established for Helsley and figured out the difference between that and the $6.9 million in arbitration Helsley was owed. That means Helsley is currently set to make $10.1 million less in 2025 than he could be on the open market. So in order to secure that long-term money now, Helsley would shave some money off of his market value and be getting a raise this year.
2. I prioritized keeping the AAV in 2025 and 2026 a bit lower than 2027-2029, which is why he is set to make $12 million and $13 million in the first two years of the deal. That's a $5.1 million raise this year and about a $4 million discount for year two, but he makes up more of that money in the final three years of the deal.
3. If you just add up the AAVs of years one through five, you'll get $70 million, which is an AAV of just $14 million. But in this scenario, I added a $5 million buyout to the mutual option year, guaranteeing Helsley $75 million over the course of the deal. If Helsley opts into the sixth year but the Cardinals decline, Helsley is paid that $5 million buyout and able to get another contract on the open market. If both sides accept, Helsley is paid $17 million in 2030.

If the Cardinals can get a deal like this on the table and Helsley's camp signs off on it, then this could make a lot of sense for St. Louis. Helsley could bring them back a nice haul in a trade or a draft selection next offseason if they hit him with the qualifying offer, but it's also near impossible to replace a closer that is as dominant and trustworthy as Helsley has been.

Helsley is represented by the same agency as Nolan Arenado and Lars Nootbaar, and the two sides have had extension talks in the past. I do think Helsley would like to get long-term security now, and I'd be curious to see how close this would be to getting a deal done for him.

It is still very possible that the Cardinals trade Helsley this offseason, but if they don't, the front office should be exploring an extension and seeing if they can make a deal happen that is beneficial to both sides.