Which outstanding 2024 Cardinals deserve an extension?

I'll start by saying this is one of my favorite cover photos that I've used in any article. Just look at how happy these two are!

Anyway, now for the important stuff. Let's talk about contract extensions.

An organization that extends a player who is in arbitration or pre-arbitration a contract is taking a bit of a gamble. The player is young; there isn't a large data sample to work with. However, if the player ends up performing above his skis, then the organization will have to pay the player a significant amount in arbitration and possibly lose that player to free agency after 6 years of service with the team if an extension isn't agreed upon. That's risky.

From a player's perspective, the exact opposite is true. Signing a contract extension allows him security, knowledge of where he'll play, for how long, and how much he'll make. If the player plays well, he'll likely surpass what he would otherwise be making through pre-arbitration and at least the early years of arbitration, but he'll make less than he would have through free agency.

It's a risky business, and the Cardinals have had some deals sour on them relatively quickly while others were absolute bargains. Tommy Edman's extension was the most recent one, and that hasn't started off strongly due to his injury.

While there are several players on the roster this year who fit the bill of a player in arbitration, only some have shown that they deserve an extension. Some players who would have made sense recently don't as of now. Jordan Walker is in Memphis and figuring out his swing, Lars Nootbaar has played well when healthy, but his health has been questionable, and Nolan Gorman is too streaky for my comfort.

That leaves Brendan Donovan, Masyn Winn, JoJo Romero, Alec Burleson, and Ryan Helsley as players who have had success this year and are in arbitration or pre-arbitration. Each of these players has outpaced his preseason projections this year and given John Mozeliak a reason to lock them up long-term. They're all reaching free agency naturally at different times, but both they and the team would benefit from signing an extension now.

Which of the 5 Cardinals who are playing well this year are deserving of a contract extension?

Extending Masyn Winn doesn't make sense...yet.

Masyn Winn has been one of the best players on the Cardinals this year. He's accumulated 2.6 bWAR in just 73 games, he has a 113 OPS+, and his defense has been stellar for the most part. He's committed 10 errors, but his plus-plus arm has saved plenty of runs already. Winn's combination of offense and defense that he's put on display so far has been admirable.

However, Winn has barely eclipsed 100 career games. Several young players have received extensions before playing as many games as Winn has (Colt Keith, Corbin Carroll, Michael Harris II, to name a few), and some of those have already been somewhat regrettable. Mind you, we're talking about players who haven't even hit 25 years old yet, though, so their fortunes could change quickly.

Masyn Winn isn't yet 23; after this year, he still has 5 more years of team control left with the Cardinals. They would be wise to wait on signing him to see if he can replicate this success in his second full season. His price tag would go up rather quickly if he can be an above-average batter while providing fantastic defense, but that's the price the team will have to pay.

Winn isn't to this level yet, but the Kansas City Royals waited to sign their superstar, Bobby Witt Jr., until this past offseason to ensure that he was as good as advertised. The Cardinals should do the same with Winn. He's likely to go to many All-Star games and receive multiple Gold Gloves. The Cardinals should absolutely extend Masyn Winn, but they should wait a little longer to make sure his success early this season isn't a facade.

Extending Ryan Helsley now would be a huge win.

Ryan Helsley is the best closer in baseball right now. He is the league leader in saves, he has a 2.68 ERA, and he's on pace to eclipse 2.0 bWAR as a reliever this year. Those are huge stats for someone who will likely throw fewer than 80 innings in the regular season. Extending Ryan Helsley now is essential to the team's success both now and in the future.

Helsley has one more year of arbitration next year, so the Cardinals are running out of time to extend him. He agreed to a contract worth $3.8 million after going through the arduous arbitration process in the 2023 offseason. I would imagine that Helsley doesn't want to go through the bartering again this upcoming offseason. A contract extension will allow him to forego bargaining and disputations with the team.

Another benefit of a contract extension would be the Cardinals' ability to work on transitioning him back to being a starting pitcher in the future. Helsley has great value as a shut-down reliever in the back of the bullpen, but he would provide even more value as a bona fide starting pitcher, a role he once held as a prospect. If the Cardinals can stretch him out this offseason and slowly ramp up his stamina with a 4-year contract, they could find a mid-rotation starting pitcher in their now closer.

A 4-year deal for Helsley would likely land somewhere around $40 million like Jordan Hicks's contract this past offseason in free agency. Hicks signed for $44 million over 4 years, and he was a true free agent. Helsley's lone year of arbitration left will lower his price tag slightly. The Cardinals could choose to keep him as a reliever, but with guaranteed control, they could transition him back to a starter to squeeze more value out of the flamethrowing righty.

The Cardinals should lock up Brendan Donovan with an extension.

Brendan Donovan emerged as a clubhouse leader this offseason. After a year that featured a void of leaders among other issues, Donovan stepped up to become a voice in the clubhouse. Despite being only 27 and having played for just 2 years, the utility player became a leader amongst a group of veterans.

Along with his clubhouse strengths, Donovan has proven himself on the field. After a slow start this year, he's managed to turn it around quite well in the month of June. His .269/.355/.418 slash line on the year is a bit down compared to previous seasons, but his OPS+ of 114 is about in line with his career average. Offense is down across the league, but Donovan has been able to maintain his production. Donovan's on-base skills paired with a boost in power since his rookie year make him a very strong offensive player.

Donovan's Gold Glove defense also bodes well for his contract extension. He won the first-ever National League Utility Gold Glove Award in 2022, and he finished 3rd in Rookie of the Year voting that same year. He has filled in quite well in left field this year after the team faced a plethora of injuries to its expected outfield corps. He's been a plus defender (1 Out Above Average) in left, and he's also seen time at third base, second base, and right field this year.

Brendan Donovan is in his final year before arbitration, so he won't be a free agent until after the 2027 season. That's 3 more years of team control. It's getting to be time for the Cardinals to extend the left-handed utility man. Donovan has become a leader in the clubhouse, he's shown consistency across all 3 years on both sides of the ball, and he provides the manager with flexibility when making a lineup. I would love to see Donovan receive a contract for 5-6 years.

Waiting to extend Alec Burleson makes the most sense.

Alec Burleson has finally been able to put it all together this year. He was given a starting slot when Jordan Walker was demoted and while Dylan Carlson was out with an injury, and he's taken full advantage of it. Burly was a part of the stellar 2020 Cardinals' draft class that included Jordan Walker, Masyn Winn, and Tink Hence. He was once overlooked out of that group, but he's starting to make a name for himself.

This is Alec's third season in the majors, but he's getting a full run for the first time in his career. The 25-year-old outfielder is slashing .282/.315/.467 for a 120 OPS+, and he's been the most consistent offensive player on the team outside of Willson Contreras and Masyn Winn. He's already hit 12 home runs, and his 14% strikeout rate ranks in the 90th percentile in baseball.

Burly is by no means a defensive stud, but he's much improved this year in the corner outfield after an offseason remake. He's been worth -5 Outs Above Average on the year, -2 Defensive Runs Saved and he has a 1.5 Ultimate Zone Rating. When he's hitting as well as he has and when he's paired with a stud center fielder like Michael Siani, these are defensive metrics you can live with. His arm strength actually grades out in the 72nd percentile.

Despite all of these positive signs that Burleson has shown this year, it doesn't make total sense to extend him just yet. He's in only his second year of pre-arbitration, so he still has 4 more years of team control remaining. Seeing one or two more seasons with output like this would give more credence to an extension for the lefty. It's been exciting to see Burleson come into his own this year, and I'm sure he will continue to produce at levels comparable to this, but an extension at this time feels premature.