Williams: How Soon Before Free Agency Do the Pirates Normally Trade a Player?

Small market teams have to deal with harsh realities sometimes. One of the biggest of those harsh realities is that they won’t be able to afford certain players when they reach free agency. They also must get most of their talent from the farm system, as a small market team can’t afford to build a contender through free agency. When those two realities combine, you get a situation where small market teams trade a player with a year or two left on his deal to actually get something in return for the player, all while restocking the farm system.

I’ve been an advocate for this approach. It’s something that all small market teams should do in order to stay competitive for the long-term. But there is a third piece to the puzzle. These teams must have an internal replacement for the player they trade away. You develop a replacement for your current talent, trade the veteran player to clear space for the young prospect, and then restock the farm system in the trade, getting ready for the next cycle.

This key part often gets lost when discussing when the Pirates might trade certain players. The normal talk surrounding guys like Gerrit Cole or anyone else under team control for multiple years is that the Pirates will trade them a year or two before free agency, just to maximize the return. No other consideration is given, except that when a player is about to be a free agent, he will be traded.

That’s not always the case though. The Pirates have taken several approaches to pending free agents. Some of them were traded early, while others were retained through free agency. They didn’t get a trade return for those players, but they did get one or two more years of production from them.

One thing to consider in the discussion of how the Pirates handle free agents is that they’ve only been competitive for a short amount of time. Prior to the 2013 season, it made sense that it was automatic for them to trade guys when they were a year or two away from free agency. They didn’t have a shot at contending, so there was no value in keeping a player around. The only value they could get from a player was trading him for prospects who could help when they would eventually contend. That kind of approach led to trades like Nate McLouth going a year after signing his extension, and bringing in Charlie Morton and Jeff Locke, who would help the Pirates fill out the rotation when they started contending.

The Pirates are now expected to be contenders on a yearly basis, and so the approach has changed. Gerrit Cole is under control through the 2019 season, and the 2007-era line of thinking would automatically trade him a year or two before he was a free agent, just because the Pirates weren’t going to be competitive in the next year or two. But the 2017-era line of thinking is that the Pirates could be competitive in the next year or two, meaning that Cole’s value isn’t just what he could bring back in a trade for the future, but also what he could provide in those years.

The Pirates have had a small sample size of dealing with free agents while they were a contender. To get an idea of how they have handled these situations, let’s look at what they did with their past examples. I’m focusing primarily on starters here, rather than bench players and relief pitchers, since those two areas are easier to fill.

Maximizing Value

There have been some cases where the Pirates tried to maximize value. They even tried this over the last offseason in their attempts to trade Andrew McCutchen with two years of control remaining. In that case, they had Austin Meadows waiting in the wings, and the rumors around that time had them looking at outfielders, likely to provide a stopgap until Meadows was ready.

They’ve made similar trades in the past, going back to Joel Hanrahan prior to the 2013 season. The team was trying to get over the hump of a winning season, and trying to make the playoffs. They had Hanrahan for one more season and about $8 M expected in arbitration. They traded him and Brock Holt and received Mark Melancon, Jerry Sands, Ivan De Jesus, and Stolmy Pimentel.

Hanrahan fell apart with the Red Sox, while Melancon went on to become one of the best relievers in baseball. Holt became a valuable utility player for two years, and none of the other guys really worked out. But getting five years of control of Melancon for one year of Hanrahan, plus saving money on Hanrahan’s contract (which was used to sign Francisco Liriano) was a good move.

They continued that chain last year. Melancon had two months of control remaining, and the Pirates weren’t going to be able to re-sign him. So they traded him to the Nationals for five years of Felipe Rivero, plus Taylor Hearn. Even if Hearn doesn’t become anything, Rivero’s performance is showing that the trade could be a steal, potentially getting another top reliever on the rise in exchange for a guy they were about to lose to free agency.

Of course, not all of the trades have been good. They traded Neil Walker prior to the 2016 season, getting Jon Niese in return. It would have been a better approach to trade Walker for some projectable guys in the lower levels of the minors. Dealing Walker wasn’t a huge mistake in terms of getting rid of him, since they had Josh Harrison able to take over. The mistake was trying to use that trade to fix another problem — the rotation — which ended up making it a bad deal.

In all of these cases — including the attempted McCutchen trade — the Pirates had guys waiting in the wings. Jason Grilli took over as the closer for Joel Hanrahan, with Melancon becoming a set-up man. Tony Watson took over for Melancon, with Rivero becoming a set-up man. Josh Harrison took over for Walker. Austin Meadows would have taken over for McCutchen at some point, with a likely stop-gap in between. The Pirates didn’t trade any of these guys with a question mark about who would take over.

No Value Remaining

There were a few other cases where the Pirates held on to players until they had little to no value remaining. In some of those cases, such as Pedro Alvarez and Jeff Locke, they just non-tendered them. In other cases, when a player was under contract, they traded them in what amounts to a salary dump.

That happened with Charlie Morton prior to the 2016 season. He was owed $8 M, and was traded to the Phillies for David Whitehead. The prospect side of the deal didn’t work out, but Morton also didn’t work, getting injured early in the season, and would have been a waste of money. That contract may have prevented the signings of David Freese and/or Matt Joyce later in the offseason.

They also had the infamous salary dump of Francisco Liriano, trading his final year and a half of salary, along with Reese McGuire and Harold Ramirez, in exchange for Drew Hutchison. Liriano is now struggling again, and his injury issues are back. McGuire and Ramirez have both struggled, continuing their decline as prospects, which began before the deal. Hutchison hasn’t worked out as the Pirates had hoped. The only value in this deal is that they saved money, which they used to bring back Ivan Nova and David Freese.

The hope with all players is that the team can trade them before they lose value, or continue to get value from them on the field if they aren’t traded. The fear of keeping a player and watching his value plummet may actually be happening right now with Andrew McCutchen, although the Pirates certainly tried their best to deal him, and received plenty of criticism about their loyalty for shopping him.

In each of these cases, the Pirates held on to players who didn’t have a replacement. They kept a struggling Pedro Alvarez for one more year before they non-tendered him, as there was no internal option at first base. They haven’t really been in a situation where they’ve had plenty of rotation depth, leading to them keeping Morton and Locke until they became too expensive. That’s kind of typical for back of the rotation guys though. Liriano was a different case, seeing a sudden decline in a year where he was expected to help carry the rotation. They could have gotten more value from him by trading him prior to the 2016 season, but he was viewed as a key piece for 2016 and beyond, so he stayed.

Sticking Around Until the End

It’s not inevitable that the Pirates trade away their pending free agents. They’ve kept a few players around, although all of the examples were with the team on short-term deals to begin with.

The most notable guys were Russell Martin and A.J. Burnett, who both had two years with the Pirates, and both departed as free agents. Burnett was offered a contract to return at a price he thought was too low. He signed with the Phillies, then opted out to return to the Pirates for one more year at a reduced rate. Martin was too expensive, and the Pirates replaced him by trading for Francisco Cervelli.

Cervelli had two years of control remaining, and at the start of the second year, they extended him for three more years. They did the same thing with David Freese, who was on a one-year deal, and received a two year extension with an option for a third year.

You’ll start to notice a trend here. All of these cases are examples where the Pirates didn’t have good depth at the position. They signed Russell Martin because none of their catching prospects had worked out. They traded for Cervelli for the same reason. They kept Burnett until the end, tried to bring him back, and then did bring him back because they didn’t have a lot of strong top of the rotation options.

Keeping Cervelli and Freese strays from this a bit. They could have gone with Elias Diaz (who was actually injured with an elbow issue at the time of the Cervelli extension), but extended Cervelli and made Diaz a depth option out of Triple-A. He could still take over in the future. They had Jung Ho Kang, and extended Freese for the same amount of time. At that time, the DUIs were unknown, although there were the accusations of sexual assault out of Chicago. There were also concerns about Josh Bell’s defense on the other side of the diamond. Freese was more of an insurance policy to add depth, and that paid off.

When Do the Pirates Trade Players?

The Pirates pretty much follow the trend of most small market teams, trading players or attempting to trade them only when an internal replacement is ready, or dumping them when they aren’t productive enough for their salaries. If you’re looking for a guide to when Player A might be traded, the best thing to do is to look at who would be in line to replace him if a deal is made.

If there is no replacement, expect him to remain with the team, where his value would be the production he has on the field. If a replacement is available, or about to be available, then there’s a good chance the Pirates will look at dealing him. The amount of time left on his deal really is useless when compared to the factor of who they will replace him with.

Of course, most of the rumors this year surround Gerrit Cole, and it’s difficult to judge whether a replacement is available. The Pirates have pitchers who can step into the rotation, but none who match Cole’s upside. The best long-term option would be Mitch Keller, but he’s not ready for another year, at the earliest. And then you’d have to ask how many top of the rotation guys they’d need. Do they trade Cole if Tyler Glasnow emerges to join Taillon and Nova at the top of the rotation? Or do they go with four guys in a stacked rotation at that point?

Perhaps this is why they haven’t seen a trend of trading starting pitchers with years of control remaining, but instead took the value that those guys brought to the field. If they did trade Cole early, it would be a change from their approach as contenders so far.

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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Do you think Frazier has become a potential stop gap for Meadows if McCutchen is traded?


He certainly has earned it, although I would have Meadows in CF ASAP, and worry about Starling Marte at some later date.


Tim: An excellent summary of the nuances of maintaining a competitive team on a small-market budget. I understand the theory of selling high to get quality prospects, but the Pirates do not seem to be able to get prospects on the field, except on the mound.

Under the heading of wanting to compete, we have become one of the older clubs in MLB. Many other teams have gone young with great success. Of starting position players our recent promotions have been Marte 2012, Polanco 2014, and Bell 2016.

Bill Harvey

I think the biggest assumption in the entire article is that the Pirates are contenders, this year and next.

It is time to come to the realization that this is just not a championship caliber baseball team. There has been such a focus placed on pitching, as an organization, that the position players have become subpar as a whole. Actually, the offense more than anything.

I understand the need for pitching, it is an absolute necessity, but to this point in the season, it is the offense that has cost the Pirates more games than anything else. That is saying an awful lot considering how many bad pitching performances this team has had.

If management truely believes that they have a championship contender next season, without Kang, then it makes sense to go for it. If not, then maybe they need to think about another rebuild. Either way, they need to do something, because continuing to waste good pitching, with limited offense is proving to be worse than when they had good offense with limited pitching.

Thomas H

Great article!


It’s interesting how many of our players seem to dwindle in value As they approach free agency: Alvarez, Locke, Morton, Cutch, Liriano, and even Burnett after 2013 (remember how bad he was against the Cards in the playoffs).

The only two that I really miss are:
– Martin but I was worried about a huge contract for a catcher his age at the time
– Walker but I was concerned about his back and mobility when he left had some issues

I am really curious about the counter offer for Cutch i
when we were shopping him, as he would ideally be a 4th OF on a really good team at his point. (Also, not completely sure Watson will have much value by the end of July…)

Blaine Huff

Don’t agree about AJ…he had a bad game against the Cards, but he was solid as heck in ’13.

Watson…sadly, I do concur. He peaked in ’14/15 and has been drifting downward since. Hopefully he can be somewhat hot/lucky over the next few weeks and pump up his value.


I remember reading about Burnett’s limitations after that loss and how they could be exploited in Busch stadium – which was news to me at the time. Then we started Cole instead of Burnett in game 5. And then he went on to that horrible year with the Phillies which was exacerbated by the injury.
Obviously, he proved in 2015 that he had something left but he didn’t seem like a good bet for the $15 million qualifying offer.


big time overpay chance for cole, have to at least listen to offers.Pirates have some wholes in the starting eight and only one position player on the farm with super star talent that being meadows. Remember the pirates don’t have to replace cole in a cole trade ,they just have to get more talent in return for gerrit cole. this is a once in ten year trade, Neal huntington will have several teams offering top shelve prospects, not only to stack the farm system but also the starting 8 and the starting rotation and maybe even able to dump some under performing players.


You hit on a very important point that hasn’t been discussed.

Trading a guy like Cole *is* a franchise-altering opportunity.

Huntington’s “sell” trades, starting back at the real teardown, have largely been underwhelming in no small part to the lack of talent and control he had to give up. The guys he’s traded with years of control haven’t been terribly good or young, and the guys he’s traded that were good haven’t had much control. You can hope to hit on very good role players like Melancon, but you’re rarely going to land cornerstone-type players.

With Cole, you legitimately have that opportunity.

The 2017 club was projected to be about a .500 club *with* Kang, Marte, and a 3-WAR performance from Cutch. The 2018 club, without significant outside help, won’t be projected to be much better, if at all. Is that really the kind of ballclub you risk forfeiting a franchise-type talent you’ll have for six years on?

Win cycles are very real in this game, and the Pirates simply are not on top right now. This is a huge opportunity for them to get back there.


I don’t think pointing out how a player performed after he left the Pirates is relative. Different team and circumstances. To me it’s similar to when a guy is thrown out stealing and then the batter hits a home run.
Not a given he would have hit the home run with runner on base.


Surprisingly, with the additions of a key couple of prospects from here, namely Meadows, Kingham and one of the relievers, the Bucs can have a really good core. Polanco, Meadows, Frazier, Bell, Tallion, Glasnow, Rivero, Kuhl and Osuna will keep the Bucs in good shape. Add In Marte, Freese, maybe Kang, Nova, and it’s not all that bad. The payroll will be cost effective and they still have control for 3 to 5 years as well. Plus add in the prospects from a Cole trade and that is the way to go.

Blaine Huff

If Cole’s going to be traded this summer, let’s just hope Dave Stewart takes a GM job somewhere before it happens.

David Lewis

Or Ned Colletti

Ben E

Great stuff, Tim.


I’d consider Nova replaceable internally. Him and Watson to Houston. Cole to NY. Of course Cole’s replacement would be needed in these deals. Waiting two years for Keller to be his replacement might be more of a gamble then the haul of potential replacements these deals would net.


Taking advantage of a trade partners need to win with adding a player will always be there. Cole if he continues to show good things, will certainly be in demand. How much will depend on the offer. But PR is gone and only winning will restore that. Bucs will have some cash to deploy next season with Cutch, Watson, Jaso maybe J Hay although Bucs will eat some of that 10 million or take back a suspect contract that is a better fit. But that is still some real coin to work with. I keep Cole as his value can go up and bring a game changing offer. With Tallion, Nova, hopefully Glasnow, Kuhl, and then who ever steps up, that may be enough with a better offense to win.


I suspect a player’s cost factors into the trade equation as well. I have the sense the Pirates are trying to build the best team they can for $100MM, and getting much over that is painful. If Cole’s salary jumps next year (in Arb), who do they let go to make the budget work? And, given they have about three pitchers bumping against the door in the minors, doesn’t that make a trade of Cole more likely?


Great article. Personally I’m in the camp to trade Cole. But we fans can go back and forth on the merits of that strategy. I appreciate the historical perspective to understand what the Pirates are likely to do. Which suggests I should temper my optimism. Oh well.


Maybe we could talk a team into taking Cutch by playing his LHP platoon numbers? 🙂

Matthew R

I keep staring at Cutch’s sub-.220 BABIP and wonder how much it’s just him getting snakebit. Yet the number refuses to rise.


Slow rollers to the left side of the field have a hard time getting through! Last year he was the worse fielder, he is now becoming the worse overall player.


There’s nothing snakebit about the weak grounder to the left side.

john fluharty

Yep. He tries to pull everything, which causes those ground balls and is at least partially responsible for the low BABIP.



I can see the buccos dealing Watson but my question is what do you see as a return for McCutchen since his struggles seem to be more than one bad year

Arik Florimonte

I think the only way they can trade Cutch is in a change-of-scenery deal, where you get a similar player with similar contract and similar fall-from-peak and hope both guys turn it around. I don’t know who that might be.

I can’t see any team wanting Cutch right now. His trade value is at an all time low, it doesn’t make sense for the Pirates to deal him.

Blaine Huff

I think the really interesting thing will be is what happens in the off-season if Cutch hasn’t been traded and doesn’t see a major uptick in performance.

There’s a very real possibility the team may pay him $1M to go away…pretty much something no one foresaw 14 months ago.

Ben E

I wonder how the organization puts value on fan sentiment versus baseball value.
Which scenario is optimal:
1. Trade Cutch and experience the wrath of an understandably sad and sentimental fan-base that might stop going to games for the rest of the season.
2. Keep Cutch through the end of the season, give hints that he won’t be back and let the fans show their love even thought the team might win more games with his replacement.
3. ?


Ben: #3 could be hold onto ‘Cutch another year, and start to stir the water on a Marte trade. When your best player, team leader, and perennial MVP Candidate suddenly becomes absent physically and mentally, is it him or the organization? I think it is the organization.

The Manager and Hitting Instructors are either not working with him or he does not trust them enough to listen to the advice. Is he salvageable if the personalities change? I would sure as hell be willing to try before we give away an amazingly talented individual, and civic icon.

Brian Z

winning cures all fan’s anger/sadness. It’ll suck if/when Cutch is traded, but win and the fans won’t care.


Especially to a team that is close to the wild card, but they really know they are not going to make it. They can tell their fan base, that they added salary and a former MVP at the trade deadline because they are trying.

If Cutch wasn’t named Cutch, he would be, at best, a 4th outfielder on a team. With the caveat, that a team would sign him as 4th outfield. I would say he’s below average-passable in the field, with no hit tool, but some power.

Tim, can you do an article about the pirates players would scout at now? That could be cool, seeing the scouting grades at the beginning of the year, middle, and at the end. I bet, Cutch’s 20-80 numbers would not be pretty


I really don’t want to see Cole traded as I still think it’s possible for this team to make a run at a WC, given the competition. But that pretty much all depends on Cutch. He’s an anchor dragging the ship down at this point. If he can’t find himself, then part ways.
So if Kingham is on track and Keller continues to progress to and through AAA by next year, maybe I can swallow that deal. Cole should get a pretty good return – but there has to be an MLB-ready OF or SS in that package.

Michael Sankovich

The Pirates making a run at the WC this season; I just don’t see it. The talent at the MLB level just isn’t there. Offense and defense both below average. I would take the possible public relations hit and trade Cole right now if they could get a good package of players in return. We are not a playoff contender with him this year, act while he still has high value.


I understand the negative view. My personal view is that Cutch alone cost this team 3 games. Even with all the other noise, those 3 wins would have Bucs at .500. And anything can happen from that point. Get Taillon back, bump Neverauskas and Santana to the big club, add Kingham when ready, Marte comes back to prove himself… still a lot of good things that can happen.

But that matter about Cutch…

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