Williams: Bryan Reynolds and the Pittsburgh Pirates Are Ready to Contend

Bryan Reynolds and the Pittsburgh Pirates just agreed to the largest deal in team history.

The deal, first reported by Jason Mackey, is for $106.75 million and runs through 2030, with a team option for 2031. It could pay as much as $124.75 million over the duration. Reynolds will be 36 in the 2031 season.

This deal doesn’t include an opt-out. According to Mackey, it includes a limited no-trade clause of six teams.

This is a legit Major League extension.

And it has changed how we should look at the Pittsburgh Pirates.


On December 3rd, 2022, Bryan Reynolds requested to be traded from the Pittsburgh Pirates.

By the end of Spring Training, he and the Pirates were discussing an extension. There were public negotiations regarding an opt-out, contract amounts, and his previous trade request lingered.

Reynolds and the Pirates have now agreed on a deal, which came a little over a year after they agreed on a two-year extension. That extension was a placeholder, meant to smooth the relationship after Reynolds took issue with the arbitration process. That extension got Reynolds under contract for this season, avoiding him going through the same process again.

That extension led to the real extension.

Last year, prior to the two-year deal, I wrote about the Reynolds extension in relation to the next Pirates contender. I’m going to highlight this part of the article from last March to show how the team has changed in a year.

The first question we have to ask ourselves is when will the Pirates contend?

I can see that happening in 2023. That would require good results from the young prospects making their way to the majors this year, a good offseason next year fueled by the money they’re definitely not spending now, and of course Reynolds still being on the team.

At the time, there were a lot of mental obstacles to deal with when trying to imagine the Pirates as a contender in 2023. You can only imagine the trepidation on the part of Reynolds to consider a long-term extension with the organization.

Major League Baseball has a pretty unfair system for young, elite players. At the age of 26, Reynolds hit for a .302 average with a .912 OPS. That was worth a 6.2 fWAR, and earned him the 11th most vote totals for the NL MVP award.

That off-season, he submitted $4.9 million for his first year of arbitration. The Pirates countered with $4.25 million. That led to frustration from Reynolds. They later made the difference right with the two-year extension.

While Reynolds was working out his two-year extension last year, the Pirates extended Ke’Bryan Hayes through the 2029 season, with a club option for 2030. With the extension of Reynolds, the Pirates have the leader of their infield and the leader of their outfield under team control for the rest of this decade.

It’s 2023, folks. And the Pirates are already looking like contenders at the start of this stretch, with Hayes and Reynolds currently at the top of the lineup.

Williams: Variability, Versatility, and Victory

The 2022 group saw the arrival and initial MLB developments of Oneil Cruz and Jack Suwinski. Cruz will join Hayes and Reynolds at the top of the order when he returns. Suwinski has been adding power to the team in his absence. Rodolfo Castro made strides with his swing decisions by the end of the year, which are carrying over to the 2023 season. Ji-Hwan Bae made his arrival by the end of the year, and opened this season back in the big leagues. The Pirates saw an arrival of young players.

What set the tone for this season was the offseason investment the Pirates made. They signed Carlos Santana, Austin Hedges, Rich Hill, and Pirates icon Andrew McCutchen to one-year deals. They traded High-A starting pitcher Nick Garcia for Connor Joe, who has already put up a 1.0 WAR this season, and is under team control through 2027.

McCutchen was traded for Reynolds after his age-30 season, a few years after being the first NL MVP in Pittsburgh since Barry Bonds. Reynolds didn’t need much of a reminder that, historically, the Pittsburgh Pirates don’t pay their MVP-level outfielders to remain in Pittsburgh long-term.

McCutchen is now back at the age of 36 — the age Reynolds will be if he plays out the remainder of his deal in Pittsburgh. He’s also having his best season at the plate in years, and has said that he might not be finished after this year. The fountain of youth has apparently been at the point where the three rivers meet in Pittsburgh all this time, because the other veterans on the team are playing like much younger versions of themselves.

Perhaps this is all a sign of the change that has been taking place throughout the Pirates’ organization.


We’ve seen the Pirates attempt to build contenders with prospects. There had yet to be an investment in the MLB team under Ben Cherington’s rebuild.

The typical disclaimer with prospects is that you can’t build a winning team on young players alone. The idealistic prediction that all of the prospects will arrive and give the General Manager a reason to go out and add the good players ignores the human element. Who is going to teach and inspire those prospects to play like good Major League players in the first place?

The Pirates took the right approach this offseason, bringing the veterans in to lead their arriving group of young players. I’ve written a lot over the last year about the individualized approach the Pirates are taking in the minors with their player development. Players are given an unprecedented level of control over their careers and development, while being surrounded by more resources than ever to develop their skills. The players who want to reach the majors will have a better chance of reaching Pittsburgh and succeeding now than in the past. When they arrive, they’ll know it was because they made the moves to reach the majors, and not because they were guided there under a strict program designed not for them but for every player.

One paradox to this approach was the tacit understanding that no player is really under control of their career in Pittsburgh.

Up until this point in time today, there had not been an example of a player in Pittsburgh who arrived through the farm system, had tremendous success in the majors, and then… just kept playing for Pittsburgh for the rest of his career.

The extension of Reynolds changes our understanding of how the Pirates will operate going forward.

When Hayes was extended, it was similar to the type of extension that McCutchen received. Hayes will be a free agent after his age-33 season if his option is picked up. He could get another multi-year deal after that, but the Pirates haven’t actually kept many players deep into their 30s.

After the extension of Reynolds to age 36, and after seeing the Pirates finding success with Santana and McCutchen in their mid-30s, we can now envision a scenario where Ke’Bryan Hayes remains a Pirate for his entire extension. If the current Pirates are going to trust 36-year-old Andrew McCutchen, and they’re going to extend Bryan Reynolds to age 36, then why would we assume that Hayes is gone when he reaches age 30?

This all makes me wonder what might have happened with McCutchen had the Pirates extended him long-term during their playoff run. He was putting up 7-8 WAR seasons, then combined for 7 WAR total in the final three years of his extension. There was constant talk about whether he’d be traded, how much decline he would see, the value he would provide at a higher salary, and so on.

I know all of this, because I wrote some of those articles. I’m just a writer with a business degree and an Out of the Park/Moneyball approach to the game of baseball. My words might help to shape the public discourse, but it’s ultimately on the people running the Pirates to shape reality that we all react toward.

McCutchen was an MVP. Then he got shipped a few years later to San Francisco. Then New York in the same year. Then, at the age of 32, he had his first opportunity to sign with any team he wanted.

How much of his downfall was worrying about the inevitability of that situation, regardless of his success? Having zero control of where you go and who you play for can impact your career. It removes the incentive to perform at a high level when you know the other side might not be as committed long-term. Having no consistency or routine from constant moving around can make it difficult to maintain a high level of performance.

Reynolds won’t have to worry about that now. The Pirates could still trade him, but he has some control to limit who he doesn’t want to play for. He’s got generational wealth, and his contract is secured with any team through the rest of the decade.

What I wonder is how much will this impact his performance on the field?

How much can he relax now that his situation is secure, no longer having to worry about performing for his pay? He doesn’t have to worry about whether he’ll be sent back to San Francisco, or to any other team as part of a 4D chess strategy move to contend in the long-run. How much can a consistent routine in Pittsburgh for the next eight years help Reynolds to be an actual MVP award winner during those eight years?

How many players will sign after him?

How many free agents will now see Pittsburgh as a destination where you can play with Reynolds, Hayes, and whatever fun veterans they bring in?

Most importantly right now, how will the extension of their manager, and now their best player following a seven game winning streak, fuel this Pirates team into believing that they are contenders right now?

The Build is over.

The Pirates and Bryan Reynolds are ready to contend.


**I love seeing the power from Henry Davis in Altoona. Anthony Murphy wrote about Davis today, and he was the top hitter of the week in the system. In the future, I think the Pirates could have a catching combo of Davis and Endy Rodriguez — with Davis moving to the RF/DH mix and Rodriguez moving to the 2B mix when they’re not catching.

**Greensboro is a difficult place for pitchers, but Po-Yu Chen didn’t have any issues in his first two starts. He combined for two earned runs in ten innings, with five hits, two walks, and 11 strikeouts. Chen is one of the better control pitchers in the system, with outstanding breaking stuff. He does have moments where things fall apart for an inning, and hopefully those become less frequent as he gets more experience. The control and breaking stuff should allow him to continue putting up good results, despite a hitter friendly park.

**One of my sleeper picks this year was Javier Rivas in Bradenton. He opened the year striking out 21 times in his first 42 plate appearances. Last week was much better for the tall shortstop, who hit .350/.409/.550 in 23 plate appearances. What’s encouraging is that he’s struck out four times in the most recent 19 plate appearances, massively cutting down at that 50% rate to start the season.


Jeff Reed previews who the Pirates farm system takes on this week.

Pirates Prospects Daily: Minor League Opponents Packing a Punch and Medical Kits

Tim started Pirates Prospects in 2009 from his home in Virginia, which was 40 minutes from where Pedro Alvarez made his pro debut in Lynchburg. That year, the Lynchburg Hillcats won the Carolina League championship, and Pirates Prospects was born from Tim's reporting along the way. The site has grown over the years to include many more writers, and Tim has gone on to become a credentialed MLB reporter, producing Pirates Prospects each year, and will publish his 11th Prospect Guide this offseason. He has also served as the Pittsburgh Pirates correspondent for Baseball America since 2019. Behind the scenes, Tim is an avid music lover, and most of the money he gets paid to run this site goes to vinyl records.

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Just like Atlanta did with all their young players(Acuna, Albies, Strider, HarrisJr) the Pirates need to do with Oneil. And Roansy would be nice too but I might be asking for too much. Let’s just get Cruz, Keller and Bednar locked up(in that order).

And I’m huge David Bednar fan but if you aren’t gonna extend him and live by the fungible bullpen(like other teams have b4 and actually the Pirates have b4) then you need to trade him when his value is high.

And I get it, people will hate this comment. But you can’t stop acquiring assets and stop making good management decisions or make poor financial ones cause you are winning(or even a playoff contender).

The Pirates need to be ran like TB, SD, and I hate to say it, but Milwaukee(and it would be nice to draft like St.Louis..lol).

Again, If they don’t plan on extending Bednar(which will be expensive; AS closers are expensive) they need to be taking calls on him this offseason and have acouple replacements in mind either already in MLB or in AAA.

Last edited 1 month ago by pittsburghbob69

I’m not sure that the Pirates are contenders this year. Maybe I’m just not wanting to set myself up for disappointment, or maybe my idea of a contender is a little off. I do believe that this team will be very competitive throughout the season, and continue to be fun to watch. I can see a lot of losses like last night but within the frustration of those losses, there is positive growth from players developing their game, which makes me look forward to watching the next game.


Yes, I’m still in a wait-and-see mode. We’re 8 games above .500 but 7 of those 8 have come against the Reds, Rockies, and White Sox so I don’t feel like we’ve shown we’re contenders yet. At least, though, we’re doing very well against teams we should beat and holding our own against other teams.


A quick side note that is a bit off topic. I see that the Rays promoted Heath Hembree tofday…..Any prayer he is still on their roster and the Bucs get to face their old mate??


If the days put him in their own then they fixed him and he will have a sub 1.00 ERA. Their own is absurd.


I happened to notice today that Harold Ramirez, yes that one, now has a 133 wRC+ over 500 PA since they acquired him. Just as predicted, lol.


Reynolds, Dylan Crews, and one legit free agent set the club up for…dare I say it…DREAM OUTFIELD REDUX!


Memories… wow. Part of me will always wonder how Polanco’s career would have turned out if he didn’t blow up his body at end of 2018. He was having a pretty good year and seemed to have “arrived”.

Probably never a star or close to one but he he have had a few 2 or almost 3 WAR seasons?


Oh nooooooo!!! Which one gets traded, which one has the nagging trips to the IL because the the keep getting hit in the hands with pitches, and which one destroys their body in a freak accident on the field during a game……Take it back NMR be for the jinx sets in!!!!!!



What if Shalin turns out to be what we hoped Gregory would have been? Trying to think of who I would want as a reasonable third OF. Let me know who you are thinking of.


There isn’t an outfield prospect in the system with a chance of being better than a Hank Davis-Jack Suwinski platoon, IMO.

And frankly, that’ll even be tough to beat on the open market (no, Bob has not actually changed his ways).

Last edited 1 month ago by NMR

Agree. Would love some platoon type system with some internal guys. Save Bob money. But for now I’m dreaming we can get a Darin Erstad or Jim Edmund’s type CF. Unless Crews can hold his own in center.


Just reminded of a comment from my friend Catch the other day, they hold the rights to Connor Joe for three more years.

I could not be happier for Joe nor think of a better platoon mate for Jack.



Great read. Nice to hear how he has matured/adapted over the years. And he dropped a “Big Cat” Galarraga. Pulling for him even more now. Forgot about the Big Cat. Not to be confused with the “Big Hurt”.



I keep watching this. Who is the main dancer. Can’t make them out.


Certainly, a step forward for Pirates, now TWT if they are good enough to contend.


Good times! All I know is that waiting for the games to start each day are torture, and off days KILL ME! That is a good sign-I am so invested in this team right now!


Hard to overstate what McCutchen did for this team over that last few months. Up until McCutchen signed the narrative was “good ball players don’t want to play in Pittsburgh”. That was followed a list of supposed reasons that seemed real (no playoffs, cheap, low attendance), to those imagined by posters here (GM is bad, Manager is bad).

This narrative was significantly weakened when McCutchen said he wanted to come back and play in Pittsburgh. I remember thinking “Cutch actually wants to play here, how cool is that?”. Then McCutchen starts play really well, the clubhouse seemed good even before the win streak, then the win streak, then lo and behold Reynolds decides he wants to play here. Suddenly all those reasons why Pittsburgh was never going to be attractive to other good players seems to have all but evaporated, and it is hard to overstate how much of that was due to McCutchen.


Hey man don’t sell yourself short, you did a perfectly good job overstating it!


It is also hard to overstate the pointless insults of some of your replies


Always assume he is joking.


even when i’m serious!


Scam likely

But not tonight, not in lineup. Oh well take some time,mourning is important.


I wonder if this is the biggest contract ever given to a player on the bereavement list


After the past couple years, we’re allowed to enjoy this! Keep Bucn

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