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First Pitch: The Pittsburgh Pirates and Player Extensions

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After last night’s 2-1 win over the St. Louis Cardinals, the Pittsburgh Pirates now sit 51-49, half a game back from the third Wild Card spot.

The Pirates won on Monday night, thanks to seven innings of one run ball from starter Mitch Keller. At this point, Keller has become automatic. He’s pitched 5+ innings in 50 of his last 51 starts, with the only exception being a shortened outing heading into this year’s All-Star Break. Keller is currently sitting at 121.1 innings, so you can’t fault the Pirates for managing his workload.

Since the arrival of Paul Skenes to the majors, Keller has been one of the best pitchers in the game. His 2.76 ERA since May 11th ranks 11th out of 80 qualified pitchers. He ranks 26th with a 3.54 FIP. Those numbers are before his start on Monday is added to the mix.

Heading into this season, the Pirates signed Keller to a five-year extension. The deal bought out three of his free agent years, with Keller originally set to reach free agency following the 2025 season. The Pirates will pay Keller $15 million in 2025, $16.5 million in 2026, $18 million in 2027, and $20 million in 2028.

The three free agent years will cost $54.5 million. The record for the Pirates in free agency is a three-year, $39 million deal for Francisco Liriano. The Pirates paid a fair rate to lock down one of their best pitchers, and Keller continues to deliver, showing improvements in his fourth year in a row at the Major League level.

Extending the Core

The Pirates haven’t just extended Keller. During the rebuild under General Manager Ben Cherington, they’ve also extended third baseman Ke’Bryan Hayes and outfielder Bryan Reynolds.

Hayes received an eight year, $70 million deal, which buys out his team control through the 2030 season, with one option year at the end of the deal. His salary is very team-friendly, locking up the best defensive third baseman in the league for $7-8 million per year. Hayes has put up his worst offensive season this year, but is coming off back-to-back 3+ WAR seasons, and should still be seen as a core member of this team going forward.

Reynolds signed an eight year, $106.76 million deal, which buys out his control through 2030, with an option for 2031. He’s taken a step forward with his bat this year, putting up his best numbers since his 6.3 WAR season in 2021. The 2024 All-Star has been the most consistent hitter on the team, with a 25-game hit streak in June that fueled the Pirates’ turnaround.

It’s important to note when each player signed their deals.

Hayes signed at the start of 2022, following back-to-back 1.9 WAR seasons. One of those was a really good September in a two month 2020 season. The other was his rookie campaign, in which he showed his elite defense and potential to add value with the bat.

Reynolds was extended prior to the 2023 season. He had his monster season at the plate in 2021, and continued being productive with a 2.8 WAR in 2022. He also had a 3.7 WAR during his rookie season in 2019.

Keller’s extension this year comes after he put up a 3.3 WAR in 2023. That was an improvement over the 2.1 WAR he had in 2022, which was an improvement over the 1.1 WAR he had in 2021. He might settle in as a 3-4 WAR pitcher, and getting that level of production at the price the Pirates paid is a good investment for any team.

Deserved Extensions

If you look at the results from 2021-2023, you see a trend.

Reynolds was the most productive player on the team during this three-year stretch, with an 11.3 WAR. Hayes was second, with an 8.2 WAR. The next best hitter during this stretch was Jack Suwinski, with a 3.9 WAR. That’s a large gap between the position players extended and the rest of the team.

Keller had a 6.5 WAR, which led the pitchers. David Bednar was second, with a 4.9 WAR, and Johan Oviedo trailed those two with a 2.4 WAR to lead the rest of the group.

The Pirates locked up their three best performers from 2021-23, although Hayes was signed before he put up those two 3-WAR seasons to put himself on this list.

It’s not a bad strategy to lock up the guys who are tangibly your best performers. This shows a commitment to spend money on the best players on the team, aiming to keep them in Pittsburgh a little longer.

Who should join the trio of Reynolds, Keller, and Hayes in the future?

Future Pirates Extensions

On Tuesday night, Paul Skenes will take the mound for possibly the biggest game of the season, and maybe the biggest game of Ben Cherington’s time with the Pirates. A win from the rookie pitcher will give the Pirates a series win over the Cardinals, while tying the two teams in the standings in a tight Wild Card race.

Skenes has been arguably the best pitcher in baseball since he arrived. His 1.90 ERA ranks first, and his 2.57 FIP ranks fourth among those same 80 qualified pitchers that I mentioned with Keller’s stats above. There’s no doubt that Skenes would be at the top of the list as the next guy to be extended.

If Skenes were to win the NL Rookie of the Year award, he’d receive a full year of service time in 2024, despite arriving on May 11th with less than a full-year remaining on the schedule. This would put his free agency following the 2029 season.

The Pirates would have five more years of Skenes, without an extension. He would be entering his age 28 season as a free agent, and there’s no question that he’d command a record-deal if his next five years go anything close to the way this one is going.

As such, any extension for Skenes would likely command a record deal for the Pirates, with some of the highest salaries they’ve ever paid in his free agent years. The deal would likely end up in the $150+ million range. The benefit the Pirates would get in signing him so early is that they could spread the cost of those later years across some of the earlier years when he would normally only be making $1 million or less.

If a Skenes extension were to take place, it would be an offseason discussion, after his future free agent timeline is more clear.

Beyond Skenes, there are two candidates for extensions on the current team.

David Bednar has been one of the best relievers in the game since joining the Pirates. Relief pitchers aren’t known for their year-over-year consistency, so there’s some risk in adding Bednar to an extension. He’s currently under control for two more seasons, and would be a free agent entering his age 32 year.

The Pirates could ride it out with Bednar on a year-to-year basis, avoiding the risk with relievers. They could also offer him a shorter term extension, buying out 1-2 years of free agency, with the help of option years.

Oneil Cruz has the highest ceiling of any position player on the team. He has emerged as one of the better players on the team this year, with his 2.1 WAR keeping pace with Reynolds on the position player side. One challenge with Cruz is his future projection. Is he a 4 WAR player or is he a 6 WAR player?

Cruz is under team control through the 2028 season, and would be a free agent in 2029, heading into his age 30 season. Are the free agent years at that point going to be 4 or 6 WAR seasons? The difference means tens of millions, and this is the first season that Cruz has been performing at the MLB level to have such a discussion. It’s hard to say what his future value is, but Cruz is starting to put himself in the tier of the team’s top performers.

I think you can make an early argument for Jared Jones or Nick Gonzales to be extension candidates. Like Cruz, we’re just starting to see what each player can do at the Major League level. There’s also a replacement factor.

Gonzales, for example, will be a free agent following the 2029 season. By that point, Termarr Johnson could already be the second baseman in Pittsburgh. Gonzales is currently in his age 25 season, and Johnson will be in his age 25 season in 2029.

Jones is also currently set to be a free agent following the 2029 season. The Pirates are an organization rich with pitching talent, and they could have a rotation that would make Jones expendable at that point. On the flip side, Jones has a higher upside than the majority of pitchers in this system, and he’s currently in his age 22 season. He’ll be a free agent heading into his age 28 season, and he should still be very productive during those years.

Skenes, Cruz, Jones, Bednar, and Gonzales all deserve consideration. I don’t think the Pirates need to rush on any one of those players right now. They should explore the possibility of an extension for several of those players before next season begins.

Based on what we’ve seen so far, the Pirates will show a commitment to extending their best performing players. And we’re now in a season where they have more than just three players performing to the point where they’d warrant extension talk.

Pirates Sign Five Draft Picks

The Pirates announced the signings of five of their 2024 draft picks, locking down picks 6-10 from day two. I wrote about each of the players they signed in yesterday’s article on the moves. The only bonus announced as of this writing is sixth round RHP Matt Ager, who signed for $2,500 below slot. Follow the Draft Pick Signing Tracker for the latest signing updates.

Pirates Sign Five of Their 2024 MLB Draft Picks

Pirates Prospect Watch

Thomas Harrington and Termarr Johnson highlighted a short week in the Pirates’ minor league system. Harrington struck out double-digit batters for his second start in a row, while Johnson continued a more impressive streak of recording a hit in 15 straight games. Read about all of this past week’s top performers in the latest Pirates Prospect Watch:

https://piratesprospects.com/2024/07/pirates-prospect-watch-thomas-harrington-and-termarr-johnson-lead-the-top-performers.html

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Tim Williams
Tim Williams
Tim is the owner, producer, editor, and lead writer of PiratesProspects.com. He has been running Pirates Prospects since 2009, becoming the first new media reporter and outlet covering the Pirates at the MLB level in 2011 and 2012. His work can also be found in Baseball America, where he has been a contributor since 2014 and the Pirates' correspondent since 2019.

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