This past Friday The Players Tribune published an article entitled “Dear Pittsburgh” by Andrew McCutchen (written by a ghost writer but the words and ideas are his). Andrew writes about what being a member of the Pittsburgh Pirates really means to him and how he has dealt with the previous season, trade rumors, and position change. He’s honest about how he felt and how the organization treated him. All told it makes a die-hard Pirate fan, like me, love him even more. It is definitely worth the read, as are most articles from The Players Tribune. There were a few big takeaways. First, he has embraced his new position and seems ready to take this season by storm:


I wanted to get back to being the player I knew I could be. The player the Pirates need me to be. And, as it turns out, what they need me to be is the best rightfielder in Major League Baseball.


The second takeaway, and the reason for this article, comes in the very last line:


I’m a Pirate. I don’t want to be anything else.


This isn’t the first time McCutchen has mentioned a desire to be a career Pirate. Around this time last year he had said that he was open to extension talks, but the front office never approached him. Even after a terrible season where some fair-weather fans turned on him, trade rumors were flying, and it seemed as a lot of the Pittsburgh fanbase was ready to let go, he still has a desire to play in Pittsburgh. I would personally love to see McCutchen stay in Pittsburgh. Players hardly ever stay with one team anymore and it would be amazing to have McCutchen achieve that. He literally brought Pirates baseball back from the dead. However, I love the idea of winning championships more. Can the Pittsburgh Pirates do something they haven’t done since 1979, with Andrew McCutchen on the team? What is the future for Andrew McCutchen, the Pirate outfielder?

The way I see it there are three realistic possibilities (sorry, we can’t entertain the idea of a new owner with bigger pockets, PLEASE SAVE US MARK CUBAN!).

Source:, Danny Bollinger

*These scenarios are based on McCutchen rebounding from a disastrous 2016.

Into the Sunset:

Andrew McCutchen gets his wish and signs an extension through his age 38 season (a six year deal). McCutchen offers a slight hometown discount and the Pirates end up paying him at a reasonable price, for a former MVP. This move would tighten up money for Pittsburgh, no matter how big the hometown discount. This would force general manager Neal Huntington to do something that he really hasn’t had to yet: trade top prospects for impact players. In this scenario top prospect Austin Meadows would be blocked from ever reaching the outfield and would be traded. The Pirates could package him up and trade him away to get a decent, cheap starting pitcher (like Jose Quintana) or a positional weakness (or long-term injury). Remember that Starling Marte and Gregory Polanco both signed long team friendly deals in the last two years. That means the Pirates will have the most payroll flexibility now than they would later. Allowing them to afford more expensive (and generally more talented) players in free agency or a trade.

The most likely time to win a World Series in this scenario is 2017 and 2018. Young players like Jameson Taillon, Tyler Glasnow, and Josh Bell would only being paid the league minimum, but possibly providing lots of support to the team. Marte, Polanco, Gerrit Cole, and Andrew McCutchen would all be within the age range that usually coincides with peak ability. The player that the prospects were traded for would also hopefully become a major part of the team’s success.

The Pirates could win a World Series, by trading away prospects, and then sign Cutch to a long-deal. That’s what you do when a player hits a walk-off Grand Slam in Game Five of the World Series against the Houston Astros (that’s right I’m calling my shot).

The sad part is that the Pirates would start to emulate the Kansas City Royals of today. As the players get older and start to leave for free agency (Cole, Marte, Francisco Cervelli, etc.) the Pirates will be unable to afford them, or other free agents, due to the large contract of McCutchen. This is the sad reality of playing in a small market. The losing seasons would come but we could all sleep tight with that new World Series banner flying high.

Hold Steady:

The Pittsburgh Pirates keep McCutchen but do not extend him. Just like the “Into the Sunset” scenario, the Pirates trade away Meadows (or some other top prospect) to turn the team into a serious contender that will give Joe Maddon nightmares. The biggest difference is that instead of extending Cutch the Pirates let him walk away. The Pirates can then spend Cutch’s extension money on some other free agent, or agents. This would likely make the team more complete and they would be able to have much longer success. Pittsburgh could potentially keep Austin Meadows, hopefully meaning that the Pirates outfield continues to one of the best in the Majors.

The Pirates window for a World Series would be much longer than that of “Into the Sunset” and would probably result in more winning seasons. However, Austin Meadows is the Pirates top positional prospect and Pittsburgh is unlikely to get a great player without sending him away (he was the main asking price for Jose Quintana). This would create a weaker team while Cutch is still on contract. It doesn’t help the Pirates are playing in a division with the always successful St. Louis Cardinals and young gun Chicago Cubs. By not trading Meadows, the Pirates significantly handicap their championship hopes until Cutch walks away. Once McCutchen is a free agent the Pirates can spend money to fill holes and make a stronger team.

Pittsburgh could compete for a World Series if they trade away a top prospect. They could also wait a couple seasons for Cutch to leave and then start to seriously pursue a championship by filling the holes on the team through free agency. The core of the current would still be signed around the time Cutch leaves and it would give time for the Pirates young players to develop into solid players.

Overall, this scenario creates a bigger competitive window for Pittsburgh, at the detriment of a stronger team and watching Cutch in another uniform.


The Pittsburgh Pirates do what small markets have to do: get prospects for an impending free agent that they are unable to afford. It’s doubtful that the Pirates would pay McCutchen what deserves, even if he gave them a small discount. Last year the team was just under .500, with McCutchen playing poorly and a shoddy pitching staff. The staff is improved this year and looks like it will continue to improve over the next few years. Austin Meadows looks poised to create more offense and play much better defense than McCutchen did in 2016. So let’s say that the Pirates improve to just over .500 without Andrew on the team and the current prospects. When the Pirates trade him away they should get a couple of major-league ready prospects. Pittsburgh would also have 14 million dollars to spread around to offer to free agents and extend star players close to the end of their contracts, like Cole or Jung Ho Kang. Alternatively they could lock-up young players to a long-term contract, like they did with Marte and Polanco.  Either way, the Pirates would start to make some waves.

The departure of McCutchen would set the Pirates back a couple of seasons. It is highly unlikely that the Pirates could seriously contend for the World Series in the next couple seasons without McCutchen and keeping prospects. However, the 2019 season starts to look pretty good though. Jameson Taillon, Tyler Glasnow, Josh Bell, and Austin Meadows all have a couple of seasons under their belts and hopefully become good starters, or better.  Cole possibly enters into a contract year and needs to prove something to land that big contract. Marte, Polanco, Cervelli, Josh Harrison, and Ivan Nova are all under contract. Add in the prospect(s) that the Pirates received in the McCutchen trade and you could be looking at a potential World Series favorite.

It would hurt to see McCutchen get traded but it creates the best chance for multiple championship. This scenario is also volatile though because prospects are never a sure thing. Injuries could cause serious issues to star players. Skeptical? Just ask the Cleveland Indians about Grady Sizemore.

The Reality:

I can sit here and continue to come up with different scenarios until my hands became one with the keyboard, but you’d get bored and I’d have the shitty nickname keyboard hands. The sentimentalist in me wants McCutchen to get a ring and be a Pirate for life. The Pirate fan in me wants to have a ring and avoid losing seasons more than anything. I think some Pirate fans would agree that 20 years of losing is still fresh in their minds. The reality is that one decision will not be the key to winning a World Series. The fans will have to trust the GM to weigh all the options accordingly.

For the time being Andrew McCutchen is a Pirate. Fans will cheer for him as a Pirate and most fans will still cheer for him if he leaves. But most of all, fans want to raise another World Series banner, with or without Cutch.

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Author Details
I grew up in the only hilly part of Indiana, an unholy place where Reds, Cardinals, and Cubbie fans all live in semi-harmony. The first 20 years of my life were abysmal as I never got to see a winning season from my beloved Pirates. Today I live in bliss as I allow my baseball addiction to take over every aspect of my life.
I grew up in the only hilly part of Indiana, an unholy place where Reds, Cardinals, and Cubbie fans all live in semi-harmony. The first 20 years of my life were abysmal as I never got to see a winning season from my beloved Pirates. Today I live in bliss as I allow my baseball addiction to take over every aspect of my life.
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