It’s been quite the offseason for the Pittsburgh Pirates. They’ve added some players through free agency and trade, while also recently clearing up some roster space by putting Miguel Yajure and Ali Sanchez through waivers (both claimed).

Turns out that is probably barely the tip of the iceberg. Reports surfaced on Saturday afternoon that Bryan Reynolds asked to be traded.

What a whirlwind of emotions the course of the day went. Initially, there were questions whether this was some sort of negotiating tactic. It later came out that the Pirates had some sort of deal on the table that would have been the largest they have given out in franchise history.

Can confirm, per sources, that the Pirates offered Bryan Reynolds a contract that would have been the largest in franchise history in terms of dollars. @JonHeyman first. Safe to say sides saw/see player valuation and years differently, but also not a nothing offer.

— Jason Mackey (@JMackeyPG) December 3, 2022

The exact figures were unknown, but there was some sort of negotiation taking place.

There are two immediate thoughts about all of this and how it unfolded, one from each side of the negotiating table.

For the Pirates, even if it was still on the lower side of things, they were actively trying to lock up a second member of this team, and not even a year after giving Ke’Bryan Hayes a $70 million contract, they were ready to go beyond that.

This happening after the trade and signing of Ji-Man Choi and Carlos Santana, as well as the ‘interest’ in Kyle Gibson (he signed with the Baltimore Orioles), it seems like there’s starting to be a shift in the focus from the previous years.

It’s still early, but there seems to be the feeling of a shift into a different phase for this front office.

When it comes to Reynolds, I’ve long been under the feeling that there was almost no reason for him not to test the free agent market. He’ll be 30-years-old when he becomes a free agent, and it could be his one big opportunity to really cash in. Why not test the open market where you can maximize on his value?

You also can’t really blame him for wanting to get out of this situation, where the team isn’t likely to be in contention again and preferring to head to a team further along when it comes to competing.

In an ideal scenario, the Pirates are able to make a last ditch effort to sign Reynolds and they get something done to keep him in Pittsburgh. While 2023 may not be the year, they aren’t far off from having a legitimate chance to compete and would be doing so while Reynolds is still in his prime years.

Sometimes things just don’t work out that way, and we get what unfolded on Saturday. With the Winter Meetings kicking off on Sunday, we can expect a lot of talk about Reynold’s trade request, and even if a trade doesn’t happen (there doesn’t seem to be a rush to make this happen), Ben Cherington could certainly leave with the framework set up for a potential swap.

Highlight of the Day

Pirates Prospects Daily

By Tim Williams

The big news on Saturday was that Bryan Reynolds has requested a trade.

Before diving into this, I want to point out a reality of the “highest paid contract” portion that is meant to show intent from the Pirates. This is one of those cases where the lack of historical spending by the Pirates allows them to say “We offered to make Bryan Reynolds our highest paid player”, and it sound nice on the surface. In all actuality, the mere act of signing Reynolds to an extension based on his value would make him the highest paid player. This wouldn’t be an act of the Pirates going out of their way, but a sad note that the market rate for a Reynolds extension is more than the Pirates have ever paid a player.

Reynolds has a guaranteed $6.75 million in 2023. I’m not sure if an extension talk would have replaced that figure and year. If it did, then the $70 million record now just needs an additional $63.25 million beyond the upcoming season for that record. Let’s give the benefit of the doubt that an extension would start after the 2023 season, like a true extension would.

The Pirates have Reynolds under team control through the 2025 season, giving them two years of arbitration. He should at least get $20 million in those years, and maybe a lot more if he has a season closer to 2021.

From there, as Anthony mentioned above, he becomes a free agent at age 30. Brandon Nimmo is in that position right now, projected to receive five years and $100 million. If we use that as a guide, Reynolds could make $120 million from 2024-2030, simply by going to arbitration two more times and becoming a free agent. He would have to maintain his production to get to this point, but that’s a disclaimer that would exist for a Pirates extension.

My guess is that a $70 million offer would have covered multiple free agent years — likely three. This would make Reynolds a free agent at the age of 33. If he’s performing well at this point, he could still get another contract to make up for not signing a big deal at age 30. If he’s not performing, he could probably still get a multi-year deal.

It’s not difficult to imagine Reynolds potentially leaving a lot of money on the table, long-term, by signing an extension with the Pirates. That’s part of the incentive for the Pirates to try right now. Reynolds only has to look at his predecessor as an example.

Andrew McCutchen signed a six year, $51.5 million extension back in 2012. The deal bought out three years of free agency. McCutchen would have otherwise become a free agent after the 2015 season at the age of 28. Instead, he became a free agent after the 2018 season, and after his performance took a downturn, which resulted in a three year, $50 million deal.

You don’t have to imagine McCutchen making more than the roughly $90 million over six years if he decides to enter free agency at age 28. Then again, McCutchen himself has said he’s not sure whether he’d have the numbers from 2012-2015, including his MVP season, without the guarantee of the contract up front.

Even though he definitely left money on the table, McCutchen has made over $100 million. Yet, chalking it up like that is as disingenuous as saying the Pirates offered to make Bryan Reynolds the highest paid player. McCutchen did make a lot of money, but comparatively, he should have made a lot more.

I say all of this to say that it really comes down to an individual choice. Bryan Reynolds is guaranteed money in 2023. He’s got a good path to high earnings in 2024-2025. He can then enter free agency at age 30, in line to receive a lot more than what he’d get at age 33.

This all assumes good performance for the next three years, and good health. It wouldn’t take much for Reynolds to see his value drop below that $70 million range discussed in an extension.

And yet, I look at Nimmo again. The biggest knock I have against Reynolds is his inconsistency. I personally wouldn’t extend him beyond age 30. Yet, Nimmo is also inconsistent, but is about to cash in because he had a big season in a free agent year.

Reynolds could do the same thing Nimmo did and put up a 1.7 WAR in each of the next two years — which would be a massive disappointment to Pirates fans — only to rebound in 2025 with a 5 WAR season for his big payday. He just needs to stay healthy enough to perform in that one season in order to make more than he’d get in an extension.

This has all been about money and value. The more important thing is whether Reynolds wants to play in Pittsburgh. There have been conflicting reports on that front, and it seems like Reynolds may have had a recent change of heart.

I’m sure this will unfold a lot more in the upcoming week as the MLB Winter Meetings take place. I can see reasons for both sides to do the deal, and I can see reasons for neither side to do the deal.

Ultimately, if the Pirates want to improve their clubhouse atmosphere, they need to handle the situation with Reynolds one way or the other.

**The other news on Saturday was that the Pirates are favorites to sign Cuban outfielder Cristian Jauregui next month.

**John Dreker wrote about Rodolfo Castro’s winter struggles in this week’s Pirates Winter Report. Castro did homer on Friday, so hopefully his issues are just offseason rust.

**Missed yesterday? Anthony recapped the moves the Pirates made to clear 40-man roster space ahead of the Rule 5 draft.

Song of the Day

Pirates Prospects Weekly

John Dreker has the latest winter report, spotlighting Rodolfo Castro, with mentions on 32 players in winter ball this offseason.

Pirates Winter Report: It’s Been a Rough Winter So Far for Rodolfo Castro