PAUL SKENES EXTENSION

Looking into why a 6 year deal for $120M might make sense for both the Pirates and Skenes

(Written in June 2025)

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BACKGROUND

Since his debut in May 2024, Paul Skenes has quickly established himself as one of

Major League Baseball’s best pitchers. The 2023 first overall draft pick concluded his rookie

season with 23 starts, 133 innings pitched, an 11–3 record, 1.96 ERA, 0.95 WHIP, 170 strikeouts,

and a 2.44 FIP. His dominance earned him a list of accolades including the fifth rookie ever to

start an All-Star Game, All-MLB First Team honors, and the 2024 National League Rookie of

the Year Award, receiving 23 of 30 first-place votes. As of writing this on June 30, 2025, Skenes

is sustaining elite production in his second season, posting a 2.12 ERA, 0.91 WHIP, and 2.50 FIP

across 106 innings in 17 starts. In those 17 starts, he has pitched at least six innings and allowed

2 earned runs or fewer in 12 of those 17 outings.

With this level of performance comes a certain level of pay...eventually. Skenes currently

only has 1.00 years of service time and isn’t even arbitration eligible until after the 2026 season

as he will not qualify to be a super two after this season. This means the Pirates currently are

only paying him $875,000 in 2025. It’s rare to talk about extensions so early in a career,

particularly with flamethrowing pitchers who have a tendency to get hurt, but Skenes calls for an

exception.

PIRATES HISTORY

The likelihood of an extension, especially soon, isn’t in fact all that likely given the

Pirates’ historical spending trends. While Skenes has already swirled in premature trade

speculation, which was quickly shut down, the real obstacle lies in the club’s financial track

record. Pittsburgh is not known for issuing high-value contracts. The largest deal in franchise

history is the eight-year, $106.75 million extension given to Bryan Reynolds in 2023. Their

largest free-agent contract is the three-year, $39 million deal signed by Francisco Liriano in

2015. The Pirates have consistently operated with one of the lowest payrolls in baseball, ranking

in the bottom five every year since 2017—and never above the bottom third in any season since

2011. Nonetheless, given Skenes’ star trajectory and the value he represents, it's worth exploring

what a potential long-term extension could look like for one of baseball’s biggest superstars.

SIMILAR SITUATIONS

While no pitcher brings the exact combination of talent and marketability that Skenes

does, there are a few recent precedents for early-career extensions involving frontline arms:

Hunter Greene

The Cincinnati Reds signed flamethrower Hunter Greene to a six-year, $53 million

extension in April 2023, with a $21 million club option (or $2 million buyout) for 2029.

At the time, it was the largest pre-arbitration extension for a starting pitcher whose club

control ended at or before age 29, according to MLB.com's Mark Sheldon. The deal

covers all three arbitration years and one year of potential free agency, with a second free

agent year included if the option is exercised. Greene began to hit his stride and fulfill his

potential in 2024 and has carried that success into 2025, making the extension look like a

worthwhile move for the Reds.

Spencer Strider

In October 2022, as the Braves are known for, they locked up their young star early. The

Braves signed Strider to a six-year, $75 million deal with a $22 million club option (or $5

million buyout) for 2029. The contract covered two pre-arbitration seasons, all three

arbitration-eligible years, and one (potentially two) free agent seasons. Strider signed the

deal with 1.003 years of service time, nearly identical to Skenes’ current service clock,

and would hit free agency at age 30 if the option is not picked up.

These deals provide a useful framework for a potential Skenes extension, though any

negotiation would likely command a premium given his generational upside and early

dominance at the Major League level.

WHAT A POTENTIAL SKENES DEAL WOULD LOOK LIKE

Given his elite performance, frontline arsenal, and rare marketability, Skenes would

almost certainly command a significantly larger extension than any comparison. Any deal would

need to reflect both his generational talent and his potential long-term value to the franchise.

Traditional Structure

A potential extension for Paul Skenes could follow a traditional long-term model: a

6-year deal worth $120 million, including a $3 million signing bonus paid upfront. The contract

would also feature a club option for the 2032 season valued at $35 million, with a $6 million

buyout. To protect Skenes’ interests, the club option would convert to a player option if Skenes

spends fewer than 120 days on the injured list due to a right arm injury over the life of the deal.

The payout structure would be as follows and includes the following incentives:

Rationale

The proposed salary structure balances competitive precedent, service-time realities, and

market-based valuation. The low first-year salary of $2 million is designed to preserve the

industry norm that pre-arbitration players, known as "zero-to-threes", earn less than

arbitration-eligible counterparts. For the three arbitration years, salary figures were based on

historical record-setting numbers for each year of arbitration —adjusted to 2025 dollars and

rounded up:

Year 1 (Arb 1): Dallas Keuchel – $7.25M in 2016

Year 2 (Arb 2): Jake Arrieta – $10.7M in 2016

Year 3 (Arb 3): Jacob deGrom – $17M in 2019

The $30 million annual salary in the free agency years places Skenes among the

highest-paid starting pitchers on the open market, aligning his value with current top-tier free

agent comparables. The $3 million signing bonus and $6 million buyout bring the total

guaranteed value to a clean $120 million, while also offering Skenes meaningful upfront

financial security. Lastly, the clause converting the 2032 club option into a player option if

Skenes spends less than 120 days on the injured list due to a right arm injury mirrors language

used in Garrett Crochet’s deal with the Red Sox, which includes a similar trigger tied to left arm

injuries. This addition provides a player-friendly mechanism without fully removing team

control in later years.

Why This Makes Sense for the Pirates

From the team’s perspective, the proposed structure requires a substantial early

investment—an inherent risk when committing long term to a high-velocity pitcher. However,

the primary upside is the ability to gain team control over up to three would-be free agent years,

thanks to the inclusion of buyouts in years one and two of would-be free agency, and a club

option for a potential third. While the free agent-year salaries of $30M, $30M, and $35M may

appear steep in a vacuum, they are reasonable relative to the current starting pitcher market. If

Skenes continues at his current trajectory, he could legitimately challenge the all-time average

annual value (AAV) record for a starting pitcher of $43.3M, set by Max Scherzer and Justin

Verlander. By the time Skenes reaches free agency in 2030, that figure could rise even higher due

to market inflation and what would be his young age of 27 at the time of signing a deal. As of

2025, five active pitchers have AAVs of $35M or more, and Skenes has already positioned

himself as a top-five arm in MLB no matter how you look at it. Securing his first three free agent

seasons at $30M, $30M, and $35M could ultimately be viewed as a win for the team, especially

when considering the club has the flexibility to decline the final option year for just $6 million if

performance declines. Using ZiPS projections, Skenes is expected to produce approximately 4

WAR per season over the next three years. If that level of performance holds over the life of the

contract—spanning his prime years from ages 24 to 29—he would generate approximately 24

WAR across six seasons. With teams spending an average of $8 million per WAR during the

2024–2025 offseason, that level of production would carry a market value of $192 million. The

proposed deal at $120 million would therefore represent a $70 million surplus in value, offering

the team significant financial efficiency. This makes sense given that he is still pre-arbitration

eligible for another season. Additionally, this deal would allow the Pirates to avoid the arbitration

process entirely, avoiding a potentially contentious process where clubs are often forced to

diminish a player's value in a hearing to keep costs down. For a generational talent like Skenes,

preserving a positive long-term relationship may be just as important as the financial terms.

Finally, such a contract would represent the largest guaranteed commitment in franchise history,

sending a clear message to fans about their desire to win and build around their young stars.

Why This Makes Sense for Skenes

From Skenes’ side, the most obvious benefit is the guarantee along with setting a

precedent. This would shatter Strider’s record for an extension for a pitcher with under 4 years of

service time in terms of both total guarantee and AAV. Additionally in terms of length, Skenes

will be a free agent at age 29 going into his age 30 season, or at 30 going into his age 31 season

depending on if the option is picked up. This would still allow him to be in his prime years for

the front end of a new deal and be able to sign a long term 6-8 or even up to a 10 year deal. He is

not losing out on being able to sign a large free agent deal. Corbin Burnes, at age 30, signed for 6

years and $210M. Max Fried, at age 31, was able to sign an 8 year $218M deal. So it is certainly

possible to sign a big contract at age 30 or 31 for a starting pitcher. Additionally, the highest total

payment over 3 years of arbitration for a starting pitcher is just over $32M set by Corbin Burnes.

Pitchers are known to get notably less than hitters in arbitration. Assuming an absolute best case

scenario, yet unlikely, from the player point of view, assume Skenes breaks Burnes’ record in

arbitration totalling $35M, signs signs for an all-time record AAV of $45M in what would be

first two years of free agency, and tack on roughly $2M for the year of pre-arbitration, that would

total $127M—again in an absolute perfect world for the player. Thus, the extension makes sense

in terms of total value as opposed to going year by year as it would be completely guaranteed

nearly the same amount.

FINAL THOUGHTS

It is in the best interest of both the Pirates and Skenes to come together on a contract

agreement and avoid the eventual arbitration process altogether. Should it come down to

arbitration, and it makes it to a hearing, it does nothing but damage relationships between players

and teams. The deal makes plenty of sense from their point of view locking down a superstar in

their prime years. They gain up to 3 extra years of control for what would most likely be below

market value price and most importantly, signal to fans their commitment to winning. It would

be up to Skenes to decide on his willingness to give up free agent years. The Pirates could look

to defer money as well. This would come a bigger headline number though and to put a similar

deal with heavy deferrals the structure could look something like:

The highest ever extension for a starting pitcher during their arbitration eligible years was

this past offseason when Garret Crochet signed a 6 year deal worth $170M after getting traded to

the Red Sox. Skenes is still over a full season away from even entering his arbitration years and

he would have tied that number in total value thus making this something he might be interested

in. Skenes would also be guaranteed to reach free agency prior to his age 30 season, allowing

him to sign a new big free agent contract at the age of 29 still in his prime years, while getting

paid from the Pirates still. Skenes would be getting paid by the Pirates through age 36. Another

option for the Pirates would be to make Skenes a Pirate for life and offer a long term megadeal,

however this is extremely uncommon for pitchers given injury risk, and more frequent with

position players. The only active pitchers in today’s game with contracts longer than 7 years are

Max Fried and Gerrit Cole of the Yankees and Yoshinobu Yamamoto of the Dodgers. Skenes

would presumably not sign either given the Pirates recent lack of winning and investment in the

team, as well as players’ overall desire to reach free agency at a reasonable age. So at this time, a

mega-deal wouldn’t make too much sense for either side, rather the traditional structure buying

out his first 2 free agent years with a club option for the third makes tremendous sense for both

parties involved.