To Extend or Not to Extend: Wheeler or Bregman?

For players who will become free agents after the 2024 season, the question of whether or not to offer them extensions will be a tough one for some front offices. One primary reason: when star players are this close to free agency, there’s no incentive for them to take a discount – to make it worth it for them to forego their chance at a big payday, they’re going to want full market value. 

Given that, let’s look at two borderline cases – a pitcher and a position player – and take a crack at guessing whether or not their current teams will choose to extend them.


Zack Wheeler

One common trait among the names at the potential top of next year’s market is age, and one of the biggest names among the old guys is Zack Wheeler. His contract with the Phillies – signed in December 2019 for five years at $118M ($23.6M AAV) – has been one of the best free-agent deals in recent history. Based on Fangraphs’ value metric, Wheeler has delivered $154.1M in value over the first four years of his contract, against a salary of $94.5M, for a whopping $56.6M in surplus value – and that’s including the Covid-shortened year of 2020.

Last season, Wheeler pitched to a 3.61 ERA in 32 starts over 192 innings, with a FIP at 3.15 and an ERA+ of 119 (where the league average is 100). In the first three seasons of his time in Philly, he put up a 2.82 ERA in 437.1 innings, 69 starts, with a FIP of 2.80 and an ERA of 148. 

Clearly, an increase in ERA from 2.82 to 3.61 is significant, but an increase from a 2.80 FIP to a 3.15 FIP is certainly less so. While this downturn in his numbers in 2023 could be written off as an aberration, it certainly must be a consideration for the Phillies, as it might mean that Father Time is beginning to catch up with Wheeler. 

On the flip side, 2023 was by no means a bad season, so while it may indicate that his best years are behind him, he still brings consistency and quality innings, which will be a large factor for the Phillies. For 2024, Steamer projects him for a 3.55 ERA and 3.67 FIP over 197 innings and 34 starts, a slight improvement on his 2023, but it does suggest that regression is likely, even to a minor degree. These are the types of numbers one would expect from a solid No. 2 in any good rotation, and in lesser rotations he has the dependability and mindset to be the ace. 

From a trade-value perspective, our model projects him for $53.8M in field value, against a salary of $23.5M, for a surplus value of $30.3M.

So what would an extension look like? Let’s break down the yearly options in our model:


Age at completion Years Salary Total ($Ms) AAV
36 3 117.6 39.2
37 4 152.8 38.2
38 5 188 37.6
39 6 222.6 37.1


Given his 2024 season age of 34, starting another 5-year deal now (replacing his current salary), from age 34-38, would cost the Phillies $188 million. Despite his age, our model projects that he’ll remain above water in field value until the last year of that deal, assuming of course no injury or major downturn. Again, that’s full market value – and it’s obviously a steep price – because he’s so close to free agency.

So are there any roster concerns that could make the Phillies halt at a potential extension? Taking a look at their current rotation, Wheeler and Nola take up the No. 1 and 2 slots, with Ranger Suarez, Taijaun Walker, and Christopher Sanchez filling out Nos. 3-5. Suarez is under control through 2025; Walker is under contract through 2026; and Sanchez through 2028. Walker is a fine No. 4, Suarez a solid number No. 5, and Sanchez was solid in about 100 innings last year, but could move to the bullpen in a swing role. 

In the Phillies’ farm system, top prospect Andrew Painter was looking to make the big-league roster last year before having to undergo Tommy John surgery, but still figures to make an impact starting in 2025; and two more pitching prospects, Mick Abel and Griff McGarry, are both currently slotted for AAA – albeit both are less heralded than Painter, and have yet to take that next step forward in development.

Thus, Wheeler presents a really interesting case. On the one hand, five years at $188M may seem ridiculous for his age 35-39 seasons, especially given his current bargain price of $23.5M. But the consistency and level of performance Wheeler provides could outweigh those concerns. There are also not any major roster disadvantages to keeping him long-term. So there’s a good chance the Phillies offer him something in that range, or perhaps a bit lower given the possibility of compromise between his current salary and his projected extension value.


Alex Bregman

Alex Bregman has been a mainstay in Houston ever since he arrived in 2016, and he was of course a major part of their 2017 World Series title (despite some taint from the sign-stealing scandal) and 2022 championship. In his career so far with the Astros, he’s slashed an impressive .274/.373/.487, with a wRC+ of 137. That ranks him 3rd among MLB third basemen in total fWAR (35.2) since 2016. 

Outside of his debut season, the short 2020 season, and an injury-hampered 2021, Bregman has been reliable for around 25 home runs and 30 doubles every season. Given this track record, Steamer projects a slash line of .267/.368/.459, with a wRC+ at 130, and 4.5 fWAR. Any season in line with that projection would be an incredible boost for his impending free agency, in addition to raising the value of any extension Houston may offer him.

Bregman is set to earn $28.5M in the final year of his current contract, in his age-30 season. If he were to agree to forego free agency and sign an extension now, he would likely demand that it carry through his age-37 season, to match early precedent-setters such as Francisco Lindor and Corey Seager. So let’s start there and look at the options:


Age at completion Years Salary Total ($Ms) AAV
37 8 222.4 27.8
38 9 245.7 27.3
39 10 269 26.9


On the 8-year deal, his on-field value would stay above water for the first five of those years, with the drop-offs in the last three due to age being reasonable. 

The biggest obstacle for the Astros in general has been willingness to spend money. They just signed Jose Altuve to a 5-year extension, and also have rising star Kyle Tucker and Framber Valdez to consider for extensions as well. 

So while Houston would certainly like to keep Bregman long-term, they may be forced to choose between extending only one or two of those players, potentially leaving Bregman as the odd man out. 

Further complicating matters is that Houston does not appear to have any ready internal options to replace Bregman at third base, either defensively or offensively. Their farm system is currently one of the worst in baseball, and their best infield prospect, Brice Matthews, is in A-ball, and projects more as a second baseman or center fielder than a third baseman. 

All of that leaves Bregman’s future in Houston rather cloudy. On the one hand, they clearly need him in the lineup, but may be forced to trade him or let him walk if they want to prioritize Tucker or Valdez in extension talks.



Wheeler and Bregman are both star players and are expected to be at the top of their respective markets if they choose to test free agency next offseason. Based on precedent, Wheeler seems likely to get an extension offer from the Phillies, while Bregman’s future as an Astro seems far less certain. 


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