First Pitch: When Could the Pirates Expect a $100 M Deal?

Yesterday, Pittsburgh Pirates president Frank Coonelly was on 93.7 The Fan, and discussed the likelihood of the Pirates ever issuing a $100 M contract. Coonelly said that the Pirates would eventually sign a $100 M deal, but couldn’t say when. That’s kind of a vague response that would technically be correct since it leaves the possibility of a $100 M deal open for as long as the Pirates are in existence. I wanted to take a look at the $100 M deals that have actually been given out in recent years, just to see what type of deal the Pirates would be able to sign, and what type of player they would be able to get with their money.

First, let’s take a look at the actual $100 M contracts that have been given out the last few years via free agency.


Robinson Cano – $240 M by the Mariners

Masahiro Tanaka – $155 M by the Yankees (plus $20 M posting fee)

Jacoby Ellsbury – $153 M by the Yankees

Shin-Soo Choo – $130 M by the Rangers


Zack Greinke – $147 M by the Dodgers

Josh Hamilton – $123 M by the Angels


Albert Pujols – $250 M by the Angels

Prince Fielder – $214 M by the Tigers

Jose Reyes – $106 M by the Marlins


Carl Crawford – $142 M by the Red Sox

Jayson Werth – $126 M by the Nationals

Cliff Lee – $120 M by the Phillies

Almost all of these contracts were given out by large market teams, with a few small and mid-market teams in there. Of course, the Marlins traded Reyes a year later, and the Tigers traded Fielder two years later. The only non-big market team to keep their player has been Jayson Werth.

With the exception of Tanaka, who is 25 years old, none of these contracts really look like good deals. The teams signing these deals are probably going to get star production for a few years. Then there will be a quick decline with the player being over-paid. With some of the deals, you’re looking at a massive waste of money by the end of the contract. I think teams hope for something like Cliff Lee’s deal (which still has up to three years and $77.5 M remaining), but the fear is that the deal could turn out like Josh Hamilton’s (.739 OPS in year one of the contract).

The Pirates are unlikely to sign a $100 M guy through free agency. The guys who sign those deals are usually in their early-to-mid 30s, and are looking for one final big deal. The Pirates shouldn’t want to sign these deals, as there’s a good chance they would be left with a huge waste of payroll in the second half of the deal.

The most likely scenario for the Pirates signing a $100 M contract would be an extension with one of their own players. Here are the players who signed pre-free agency extensions for $100 M or more, via MLBTR. To keep it comparable to the Pirates, I’m going to leave out all extensions signed by big market teams. Clayton Kershaw’s deal isn’t going to tell us anything about what the Pirates can do.

Evan Longoria (Rays) – 6 years / $100 M (4.170)

Joey Votto (Reds) – 10 years / $225 M (4.027)

Ryan Braun (Brewers) – 5 years / $105 M (3.150)

Troy Tulowitzki (Rockies) – 10 years / $157.75 M (4.033)

That’s not a long list, but it does allow us to dig into the extensions a little bit closer.

Evan Longoria – His first deal with the Rays (signed shortly after his initial call up) looked like a huge bargain. Longoria was set up for six years and $17.5 M, plus three option years which could have added $27 M to the deal. His extension guaranteed all of those options, then added $100 M from 2017-2023. The thing about Longoria’s deal is that the Rays don’t really have any heavy lifting to do for a long time. He will be making $15 M or less through the 2020 season. He only makes more than that in 2021 and 2022. There is also $11 M in salary which was deferred without interest. That would make his actual salaries in 2021 and 2022 $16.5 M and $17.5 M, respectively. Basically, Longoria gave the Rays a huge discount, and a contract that is easy to afford for the duration of the deal.

Joey Votto – This is a case where Votto pretty much got what his free agent value would be. There was no discount given here. The extension kicks in this year, and he will make under $15 M the next two seasons. After that he will make $20 M in 2016, $22 M in 2017, and $25 M per year from 2018-2023. The Reds paid Votto $17 M last year, so they could probably afford him at a rate close to $20 M. It will be interesting to see how the rest of their team works out. They’ve already been discussing a trade of Brandon Phillips this off-season, and a lot of writers are speculating that they will lose Homer Bailey as a free agent after the 2014 season.

Ryan Braun – Just like Longoria, Braun signed a very team friendly deal early in his career. That deal runs through the 2015 season, so this extension doesn’t start until 2016. The Brewers are paying Braun $12 M or less through the 2015 season, followed by $19 M per year from 2016-2018, then a decline to $18 M, $16 M, and a $15 M mutual option in the final three years. He also has $18 M in salary deferred without interest. That is $4 M per year in 2016-2018 (meaning he will actually make $15 M those years), and $3 M each in 2019 and 2020 (actual salary: $15 M and $13 M). I don’t know if I’d call the deal team friendly over the long haul, but the deferred payments without interest make Braun very affordable.

Troy Tulowitzki – Here is another player who signed an early extension, followed by what could be considered a team friendly deal. Tulo’s second extension replaced the final three years of his first extension. He will make $16 M in 2014, and $20 M per year from 2015-2019. There have been some trade rumors surrounding him, although it’s hard to say if Colorado is actually shopping him, or if it’s just people speculating that the Rockies could trade him. The heavy lifting starts in 2015, and that would give a better indication of how the Rockies will handle his contract.

There are two different types of deals here. With Longoria and Braun, you have players who gave their team either a big discount, a contract that is easy to pay with deferred salary and no interest, or both. With Votto and Tulowitzki, you have two players who received deals that are closer to what they would receive on the open market. Votto’s deal takes him through age 40, while Tulowitzki’s deal takes him through age 36. Neither team has started the heavy lifting yet with these two. If I had to guess, I’d say the Reds and Rockies will either eventually trade these players, or will have to let other players walk because their money is tied up in a big contract.

If the Pirates are going to eventually sign a player to a $100 M contract, I think it will be through an extension during a player’s arbitration years. It would probably also be a case where the player already has an existing extension that would have bought out a few free agent years. That player would be more inclined to sign a deal, since he would be further away from free agency.

If the Pirates signed a Votto/Tulo deal, then I don’t think the allure of a $100 M contract would be appropriate. I think the Pirates would eventually trade the player, just like I think the Reds or Rockies will eventually trade their guys. Or the Pirates will have to sacrifice several other players to make room for this massive deal.

The more likely scenario would be the Pirates getting a big discount like the Rays and Brewers got with Longoria and Braun. That would almost certainly include deferred payments, and might even include a below market contract.

Andrew McCutchen would be a prime candidate for such an extension. He’s under team control for the next five years, so he’s not close to free agency. A “Ryan Braun” type deal would make the most sense, as it would pay McCutchen close to his free agent value, while making the deal affordable for the Pirates. That’s not to say that a deal for McCutchen is a guarantee. From McCutchen’s standpoint, he could be passing up over $100 M by signing such a deal. If Robinson Cano can get $240 M in 2013 at the age of 31, then Andrew McCutchen should be able to get a massive deal at the age of 32 in 2019. From the Pirates’ standpoint, they’ve got Starling Marte and Gregory Polanco, plus a lot of talented outfield prospects in the minors. It’s entirely possible that they won’t even need McCutchen by the end of his deal.

If McCutchen doesn’t sign another extension, then it might be several years before the Pirates sign a $100 M contract. The next candidates would be guys who are just arriving in the majors, like Starling Marte, Jameson Taillon, or Gregory Polanco. Those guys wouldn’t be candidates until four or five years from now, and that all depends on their performances. I left Pedro Alvarez and Gerrit Cole off that list since both are Scott Boras clients who are unlikely to sign pre-free agency extensions.

I don’t think there should be a rush to sign a guy to a $100 M contract. It’s not like extending someone now would change the team in the short-term, and the only candidate now (McCutchen) is under control for five more years. The only other way to add a $100 M guy is through free agency, and I just don’t see that happening for the Pirates, or for most small market teams. I could definitely see a $100 M deal eventually, but it would probably come in the form of a discount to the Pirates, and an annual salary that is easy to pay, much like with the Brewers and Rays.

Links and Notes

**The 2014 Prospect Guide is now available. You can purchase your copy here, and read about every prospect in the Pirates’ system. The book includes our top 50 prospects, as well as future potential ratings for every player.

**We have been releasing our top 20 prospects for the 2014 season, and this week we started the top 10. Today the countdown resumed with #7 – Reese McGuire.

**Pittsburgh Pirates Have Six Top 100 Prospects. Plus two guys on the outside of the list. All of this comes a year after graduating Gerrit Cole to the majors. The crazy thing is that I could see them with 6+ players in the top 100 next year, and that’s after they are expected to graduate Jameson Taillon and Gregory Polanco in 2014.

**The Latest A.J. Burnett Non-Update. Basically the same thing we’ve been hearing since last March.

**Josh Bell and Tyler Glasnow Just Miss Top 10 Lists. They both made the top 100.

**Winter Leagues: Harold Ramirez Collects Two Hits In Playoff Win

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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The Nats are a unique case in baseball. Unlike the ‘skins, who have a deep rooted fanbase and have for years, the Nats are trying to build that for themselves. What makes their situation so different is that DC is mainly a transient town with people from all over the country living and working there. yes there are a lot of people living there. But not a lot FROM there. And getting to their stadium is such hassle that most people would rather not be bothered.

As far as the Pirates signing a $100 million player ? It’ll happen right about the time that EVERYONE ELSE has one.


Not in my lifetime. As far as info coming out of Pirates front office, anything said that has not already come to pass means nothing. They double talk so I don’t listen to anything that is said. Rumors from just about anyone has a better chance of being meaningful.


Here is a $101 mil extension – Andrew McCutchen, $6 mil signing bonus. His 2014 thru 2017 salaries are $7.25, $10, $13, and $14 which I think is as club friendly as anything I have seen for MVP-Caliber talent.

2018 – ‘Cutch’s Age 31 season – the Club Option in his present contract for $14.5 mil becomes a $17 mil guarantee
2019 – his age 32 season – $20 mil
2020 – his age 33 season – $21 mil
2021 – his age 34 season – $22 mil
2022 – his age 35 season – $15 mil plus incentives
2023 – his age 36 season – Club Option

Prime years for an OF probably start around age 26 and, depending upon the body type and work ethic of the athlete, could extend beyond his age 34 season, which for ‘Cutch is 2021. He is chiseled, has a great work ethic, and I am in that crowd that thinks that when he hits 30+ he will go to RF and continue to be a solid, middle-of-the-order, hitter with a few extra pounds on the frame.

Scott Skink

The Bucs wil sign a $100 million deal when inflation returns to Carter administration levels.

Anyway, it certainly won’t be Marte getting it.

Am watching MLBTV “10 Best Left Fielders Right Now”. Brian Kenny’s list has Marte 4th. “The Shredder” has him 5th. Eric Byrnes has him 7th.

Bill James doesn’t have him at all.

When Kenny asks why, James simply responds, “I don’t know what you’re seeing there.” And later he adds, “This is a guy who doesn’t really do anything well. OK, maybe the stolen bases.”

And there you have it, from the Godfather of Sabremetrics.

So which of you advanced statistics geeks is gonna be the first to call James an old fool?


Starling Marte, 22 Defensive runs saved above average; UZR of +10.1; UZR/150 of +18.4
Justin Upton, -6 Defensive runs saved above average, UZR of -9.6; UZR/150 of -11.1
Domonic Brown, -6 Defensive Runs saved above average; UZR of -10; UZR/150 of -12.6

Do you think that Bill James knows about these advanced stats? I am a real neophyte when it comes to sabremetrics, but just a difference of 28 defensive runs saved above average would have tipped me off that one of these guys is a truly outstanding defensive player. If I am not mistaken, James had Brown on his list instead of Marte. Brown is one of those former All World Prospects who is doing well, but nothing any better than Marte (possibly could K less). I also think that Marte led all qualified LF in defensive WAR.

One of the others in the NL was Bryce Harper and the other was Matt Holliday. Useless to compare Holliday defensively, and Harper has strong O and less D than Marte, but still excellent, and is still only 21.


It seems quite possible. You figure that Jason Kendall’s 6-year, $60 million contract extension was issued by the Pirates 13 years ago!! (and a lot of baseball contract inflation has happened since then.)

While the money and trying to pick out the player is interesting, any guesses as to the length of the Pirates first $100m contract? My money’s on it being something like 8 years.

Perhaps a Polanco gets an early 8-year, $100m contract extension after a couple of years in the league.


I listened to the interview, the question was poorly asked as are most of the questions Coonley gets, so expecting a good answer to a poor question usually gets Coonley in trouble because of how difficult they actually are to answer. When Coonley answers a question, he has to worry about where it leads to, he has to worry about how someone is going to interpret it, he has to worry about how the media is going to spin it and he has to do it in a couple of seconds.
The question should have been “Will we see the Pirates spending 100Mil for a player this year or next year and are there any players on this club that you would spend that kind of money on? Not “Will the Pirates ever spend 100Mil on a player?” Of course they will spend 100Mil, they will have to, but when they do 100Mil might be chicken feed. I am not defending Coonley, I understand his situation when he talks to the media or when anyone in sports talks to the media, very tough to do these days.


One important variable for long term contracts which isn’t an issue now, but will be in the future is the rate of inflation. Inflation is negligible today, but could be ripping at 12+ % per year five to ten years from now which would make long term contracts very team friendly. Even with that I would only do a long term $100 MM deal with a truly elite player, say consistent .900+ OPS for a position player, which in the Pirates case only means Cutch in this seasons line up. Others like Marte have yet to prove out their potential.


I agree with Jeff…when FC speaks, it is hard to take him seriously.

Our TV contract is one of the better ones? Right, Frank. Now go have another beer.


He seems the need to occasionally make statements like this . I agree that sometime in the future the Pirates will sign a 100 million dollar contract but it will not be in the near future .


This might be considered a quibble, but it’s something I see a lot and I think it needs correcting: “The only non-big market team to keep their player has been Jayson Werth.”

Werth plays for the Washington Nationals, so obviously you’re saying that the nation’s capital is a “non-big market”. According to a list of U.S. Metropolitan Areas on Wikipedia, Washington is the fourth most populous Metro Area in the country. It has more people than “big markets” like Boston, Philly, San Francisco, and Dallas. Sure the area is sprawling and Baltimore is now lumped in, but it’s time to stop thinking of the area as “non-big”, unless you want to define “big market” as limited to NY and LA.


It seems to me they would certainly be capable of spending $150M or more on salary. They have the population base (with the income) to sell plenty of high-priced tickets. I live in the area, and ticket prices for 100 level seats are rather steep, compared to what I’ve gotten the last couple times I’ve been to games in Pittsburgh. I know their TV revenue is limited for by the deal that bought Angelos’ agreement to bring the team here, but it seems to me they could go higher in salary if they wanted to. Maybe they’re holding back some for Strasburg, Harper, etc., but I’m a bit surprised they haven’t tried to make another Werth-like deal.


Reasonable thought… Washington felt like a smaller market for a while (at least to me) but that was probably because they were coming from Montreal. They seem lumped in that group with the Cards, Rangers and White Sox now.


Don’t they have the richest owners in baseball?


I tend to look at it more in terms of revenues as opposed to population and the Nats have a pretty good tv deal so that plus the population and I totally agree.


When Frank Coonelly speaks, I have a hard time taking much of what he says seriously.
This is similar to what he said last spring training when speaking to a question about added revenue from new TV deal. He proclaimed it would go for increasing the major league payroll. The 2014 payroll looks about the same to me. Now if AJ signs, that’s a different story.

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