The mass exodus facing the Cardinals rotation at the end of the 2023 season is well-documented at this point. Longtime rotation stalwart Adam Wainwright is set to follow in the footsteps of his longtime battery-mate Yadier Molina and retire following the end of the 2023 season, while each of Miles Mikolas, Jack Flaherty, and Jordan Montgomery are set to depart the club as free agents. If none of that group is extended, right-hander Dakota Hudson will be the only pitcher to make more than ten starts with the Cardinals in 2022 and remain with the club in 2024, though lefty Steven Matz is also under contract through the 2025 season and youngster Andre Pallante impressed in ten starts last season.
The 2023-2024 free agent class figures to be exceptional deep in quality rotation options, even for clubs who won’t be part of the Shohei Ohtani sweepstakes. Still, it seems reasonable to expect extensions, such as the one Yu Darvish signed with the Padres last week, to continue thinning the herd throughout Spring Training and into the regular season. For a Cardinals club that’s attempting to make the most of the remaining prime years for superstars Nolan Arenado and Paul Goldschmidt, going into the offseason with three or more slots in the rotation to fill would put an enormous amount of pressure on the front office. As such, it’s no wonder that the organization is reportedly planning to have extension conversations with at least two of their starting pitchers this spring.
The clearest choice for the Cardinals to pursue an extension with would be Mikolas, who reportedly is open to extending with the club this spring. Even entering his age-34 season, there’s every reason to expect Mikolas to be durable going forward; though he missed the entirety of the 2020 season and much of the 2021 season due to surgery, since joining the Cardinals ahead of the 2018 season he has pitched more than 180 innings in each of his three seasons unaffected by that surgery, including inning counts over 200 innings in 2018 and 2022. On top of that, Mikolas has proven to be an effective mid-rotation option whenever he is on the mound, with a 3.46 ERA (114 ERA+) and a 3.84 FIP in 631 2/3 innings as a member of the Cardinals.
Furthermore, despite his age and workhorse tendencies, the mileage on his arm is still fairly low: Mikolas has just 1,561 professional innings under his belt between the majors, minors, and his time overseas. That’s more than a thousand innings less than similarly aged hurlers such as Yu Darvish and Clayton Kershaw, and just a tad under the 1,746 1/3 professional innings Aaron Nola has under his belt headed into his age-30 season. Given Mikolas’s combination of effectiveness, durability, low mileage on his arm, and comfort with the club (he already extended with the team once, ahead of the 2019 season), it’s no wonder that Mikolas appears to be one of the starters the Cardinals are seeking to continue their partnership with.
What of the other options, though? Surely, if Wainwright changes his mind and decides to continue pitching in 2024, the lifelong Cardinal would be continuing his career in St. Louis. All signs point to him hanging them up this fall after the conclusion of his age-41 season, however, leaving two pending free agents in the Cardinals rotation for them to consider extending: Flaherty and Montgomery. Flaherty is the younger of the two, set to pitch in 2023 at age 27 while Montgomery celebrated his 30th birthday earlier this offseason. Both players have dealt with injury woes in their careers, though Flaherty’s are more recent, having spanned the 2020-2022 seasons. Montgomery’s struggles from 2018-2020, by contrast, have since been followed up by a pair of quality, healthy seasons.
Montgomery has also shown more consistency throughout his career; when healthy, he has reliably been good for around 150 innings of 10-15% better than league average baseball. Flaherty, on the other hand, has two exceptional seasons under his belt in 2018 and 2019 where he combined for a 3.01 ERA, 35% better than league average, while finishing top 5 in Rookie of the Year voting in 2018 and Cy Young award voting in 2019. Outside of those two seasons, however, he has just 176 career innings at the major league level under his belt, and the results of those innings leave much to be desired: a 4.19 ERA and more than a strikeout less per nine innings than his peak years.
One can rightfully argue that Flaherty, so long as he can get healthy, projects to be better than Montgomery going forward. Montgomery’s fastball velocity in 2022 clocked in just below that of Flaherty despite the fact that Montgomery was enjoying a career high while Flaherty’s velocity was at an all-time low. Flaherty’s camp will surely make that argument, and with such a considerable gap between Flaherty’s potential and his current results, it’s fair to wonder how feasible it is for the two sides to come together on an extension they both find mutually agreeable, particularly when a big season from Flaherty in 2023 could cement him among the top starters on next offseason’s free agent market. Flaherty seems, perhaps, particularly unlikely to take much of a discount given he forced St. Louis to renew his contract ahead of both the 2019 and 2020 seasons rather than agree to a pre-arbitration salary, calling it a matter of “principle.”
The Cardinals have no such contentious history of negotiations with Montgomery, whom they acquired at the trade deadline last season in a deal that sent center fielder Harrison Bader to the Yankees. Montgomery pitched extremely well down the stretch for St. Louis last season, racking up 63 2/3 innings that were good for a 3.11 ERA (123 ERA+) and a 3.08 FIP. While Montgomery’s potential is far from that of Flaherty, that dominant stretch to end the 2022 season could indicate that there is still upside yet to be tapped into for the left-hander. Furthermore, despite not being a member of the organization for very long, that hasn’t stopped this Cardinals front office in the past. After all, president of baseball operations John Mozeliak is the one who signed Goldschmidt to an extension prior to the 2019 season before the slugger had ever played a regular season game in a Cardinals uniform.
Financially speaking, the Cardinals have plenty of room to maneuver under the luxury tax going forward. The club’s estimated luxury tax payroll for 2024 according to Roster Resource is just over $106MM, down from $199MM in 2023. Granted, that 2024 figure does not include arbitration salaries for 2024. In 2023, arbitration salaries are adding $36.5MM to the luxury tax ledger in St. Louis- even if that figure repeats, the club would have nearly $60MM to play with before reaching their 2023 payroll level, and over $90MM before reaching the first luxury tax threshold. That should leave them Mozeliak’s front office plenty of room to add or extend starters ahead of the 2024 season.
For players between five and six years of service time, as Flaherty and Montgomery both are, three recent extensions have taken place: the seven-year, $131MM deal Jose Berrios signed with the Blue Jays last offseason, the five-year, $100MM deal Joe Musgrove signed with the Padres last summer, and the five-year, $85MM deal Lance McCullers Jr. signed with the Astros ahead of the 2021 season. Berrios stands as something of a clear outlier among the other two, while Joe Musgrove has been a more effective starter than Montgomery and a more consistent starter than Flaherty. As such, McCullers seems to be the most appropriate comp for our purposes.
McCullers and Montgomery both are solid mid-rotation starters when healthy, and though McCullers was just about to begin his age-27 season when he signed his extension, making him three years younger than Montgomery is now, he was coming off far more recent injury troubles than Montgomery was while having never pitched even 130 innings in a season of his career. The $85MM figure also compares reasonably to the mid-rotation market this past offseason, which each of Chris Bassitt, Jameson Taillon, and Taijuan Walker securing between $63MM and $72MM and Montgomery having an argument as a safer bet than any of them.
Flaherty, on the other hand, seems less likely to find that sort of deal appropriate. Following an offseason that saw the likes of Carlos Rodon and Jacob deGrom secure well over $100MM despite injury concerns, it’s reasonable to think that Flaherty could do the same with relative ease should he have a bounceback year in 2023, particularly given his youth. Additionally, the market was rather kind to even oft-injured bounceback types such as Andrew Heaney this offseason. Even if Flaherty struggles again in 2023, he could search for a two-year deal with an opt-out as Heaney did to rebuild his value and hit the market a second time before his age-30 season.
Given all of this, it seems unlikely he would settle for much less than the $100MM Musgrove received, and it seems even more unlikely the Cardinals would make such a risky investment at this point, even with their significant concerns about the future of their rotation. Taken together, it seems that if the Cardinals are going to look to lock up some of the members of their rotation before season’s end, they’d be better off looking toward Mikolas and Montgomery than Flaherty, even despite all the tantalizing talent he brings to the table.
Correct answer: All of them!
True, I think Monty they should try first and mikolas if he gives them a team friendly discount.
I was about to respond ‘none of them’. None of them are mainstays, IMO.
Jack Flaherty should be to make sure the Cardinals are hitting their African American starting pitcher quota.
Lost me.
I would probably say Mikolas. I think Montgomery is probable but they may want to see more. I do not see Flaherty in a Cardinals uniform in ’24 regardless of how he pitches in ’23
Yeah, we could’ve said that about Flare after his rookie year
Solid group of rotation candidates, but I’m not impressed with the position. players overall. I’m thinking that Dombrowski might extend Nola, although being this close to FA, it’s going to be challenging to do.
They will extend Montgomery I’m sure
You’re assuming he wants an extension. I’m not so sure. I don’t see them extending anyone but Mikolas. They need to trade position players for starters. They will wait until those position players prove their value. I look for moves at the deadline again. Hopefully they can package a few young players for a much better starter.
Montgomery looks good with a beard I can’t believe the Yankees were keeping that from us for so many years
Better facial hair:
Logan Gilbert?
Or Monty
I usually am alarmed to see ex-Yanks players with beards (and also guys like Carp and Paxton having to lose them), but I do agree Monty rocks that beard.
beards are for lumberjacks, mountain goats, and clams. 🙂
You forgot Shih Tzus.
The best they can hope for from Flaherty is he has a great season so they can lose him after giving him the QO.
Personally I would extend Matz, but for cheap if he agrees, Mikolas and Montgomery I would also extend.
Yeah, that’s the ultimate question: how much are these pitchers expecting? Once that’s answered the question posed in the article title is much easier to answer. Could be all, could be some, or if they’re all eyeing big money deals, the answer could be none.
Extending pitchers won’t be cheap. The market for pitchers is one of the most expensive for a legitimate starter. Guys like Quintana are making nearly double figures near 40 years of age. Rich Hill signed something like a 9.5 million one year contract. Anything good will want something in that range or higher
Why would they extend Matz?
As maybe a 5th rotation
He already is signed through 2025 and did almost nothing last year. I don’t know why the Cardinals would be interested in locking down that performance for longer than they have already.
The point is they still have him under contract for 3 more years. He’s going to have to pitch at least a full year before he’s considered for an extension.
Matz has three years left on his deal.
Flaherty is going to walk anyway. Mikolas and maybe Montgomery are the only realistic options.
Taillon has been pretty average his last 3 seasons and secured 4/68 this offseason entering age 31 campaign. Most starters in a walk year are well served to roll dice on the open market with the $ so high.
His strikeout to walk ratios were elite. I would pick on Walker if I had to choose someone here.
Ok, but consistently surrendering a lot of multi-run HRs makes the bottom line results just okay overrall. No matter-he got a great payday!
Extend Adam Wainwright for 10-years.
… at minimum wage to lower the tax hit lol
Please
Anybody have a good grasp on what the hell happened with Matz? Last time I saw him in person was summer ‘21 and he dominated us over 5 shutout innings. I was so impressed, especially since he’s a NL to AL transition guy
When he came back from a shoulder strain or something like that he hurt his knee on a play at first base the first game…bad luck…we haven’t even really seen him pitch to much lol
Couldn’t stay healthy last season and when he was pitching, had a couple bad outings that skewed his season numbers 0
He was very ok when healthy. Ideally he’s the #4 or #5 in St. Louis because there’s enough other guys ahead of him who are better.
I agree Matz is a 4 at best on a playoff team. But he’s a very solid back of rotation arm when healthy
They just referred to Andrew Heaney as a bounce back guy. How was he a bounce back candidate when he was never that good? Lol
Dude my dad and I always called Heaney “meatball,” the nickname was perfect. He would get behind and slop that 91 dead red or if the hitter was any good, he would just nibble nibble nibble nibble with absolute AAA stuff.
I know I’m coming in strong here, lol. The fact that Heaney is still in the league? He had good stats last year? I am baffled by that. Bounce back? They talking four square at home with his kids?
Monty would be a good extension if the price is right, if they could get him for 5 years 80-85 million or 4 years 65-70 million it could be a potential bargain.
I think he’s going to try and get to 90-100 million, especially with Boras as his agent. At the prices you quoted, I would be interested assuming he does well this year.
I just gee willikers at the cards. Join here for march madness https://fantasy.espn.com/baseball/league/join?leagueId=2053656043&inviteId=b96b53e6-5d3f-433e-9c39-55d8578b2f97
I like Montgomery as priority #1 because of his performance for the Cardinals, his age, he is a lefty, and because the Cardinals gave up Harrison Bader to get him. Next I like Mikolas because of his performance when healthy. As for Flaherty, I get the impression he wants to return to his home in Southern California. If Flaherty is healthy and performs well in 2023, I can see the Angels offering him a multi-year contract that is longer and more lucrative than what the Cardinals will offer. If not the Angels, then the Padres, Dodgers, and Giants. . .
Resign Mikolas! We need his cowboy energy!!
They should go all in on Tyler Chatwood
Honestly, I would see who is willing to take the least. Personally, I like each of Monty, Flaherty, and Hudson, but the elephant in the room for each is health. I guess I’d lean Monty given recent production and a lesser injury track record, but it’s not a confident answer.
When you look at the Cards their starting pitching is their biggest weakness, Fangraphs has it at 21st one ahead of the Cubs. I would think that they need to revamp their starting pitching pronto. I don’t think any of these guys that are leaving are going to put them over the top!
The Cardinals do need a true top of the rotation guy, but they have a solid but unspectacular group of starters who all seem to outpitch their numbers. The topnotch defense doesn’t hurt matters
Agreed, but they won’t win the world series without getting 2 top pitchers from somewhere.
What do they mean by “extend?”
Will Adam Wainwright make the HALL OF FAME? Thoughts?
Yes unless he speaks publicly about immigration or gender.
He gonna misgender a non binary umpire.
No. I love Waino, but he’s not a HOFer.
Highly unlikely Wainwright makes the MLB Hall of Fame. He competed for a Cy Young in 4 years. without winning one He’s hovered around league average other than those years. He will be in the Cardinals HOF.
It’ll be Mikolas for sure, and Montgomery if he’s interested in an extension. Flaherty has spoken often of wanting to experience free agency because he’s not a fan of the way the league compensates young players. People wrongly assume the issues are with the Cardinals but if you listen to what’s he said his issues are with the institution as a whole.
Jack doesn’t want to extend plain and simple he should have been dealt after Covid season.
For Jack, it would depend on his health and performance this season. If either is lacking, he may pick the “devil he knows” rather than the unknown. But if he’s healthy and performs well, he’s going FA. He wants the bag
Very little chance Monty extends. Boras is his agent. He’s probably telling Monty that there’s $150+ million out there for him!
No offense to his time in NY, but Montgomery has spoken very highly of the organization so far in his time in STL so I think there is a chance he would extend. Depends on the numbers
Montgomery is possible, but unlikely. He’s solid and will get overpaid. Mikolas makes some sense if he is healthy/effective again this year. That gives them Mikolas, Matz, and Hudson for next year. Hopefully Graceffo makes his debut and does well, so that gives you perhaps 4 guys to pencil in for 2024. The last open spot would hopefully be reserved for a legit #1. They may have to trade for one though. Shane Bieber comes to mind. Other than that, signing Giolito in the offseason seems like a fit too.