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

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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.

2013

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

2012

Zack Greinke – $147 M by the Dodgers

Josh Hamilton – $123 M by the Angels

2011

Albert Pujols – $250 M by the Angels

Prince Fielder – $214 M by the Tigers

Jose Reyes – $106 M by the Marlins

2010

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 MLB.com Top 10 Lists. They both made the top 100.

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

Tim Williams
Tim Williams
Tim is the owner, producer, editor, and lead writer of PiratesProspects.com. He has been running Pirates Prospects since 2009, becoming the first new media reporter and outlet covering the Pirates at the MLB level in 2011 and 2012. His work can also be found in Baseball America, where he has been a contributor since 2014 and the Pirates' correspondent since 2019.

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