Just how "controversial" was Jon Singleton's deal?

Jake Kaplan talked to Jon Singleton yesterday about his removal from the 40-Man roster. Singleton was predictably pragmatic about the transaction after hitting .202/.337/.390 in Fresno...

I kind of just took it for what it is. Obviously I had a down year last year. So I figured that I had some kind of consequence. But it is what it is.

I mean, what's he gonna say? "I should have gotten called up in 2016 at least once?" (That actually may be true, given the struggles the Astros endured at 1B in 2016, but whatever).

Still, Kaplan wrote this intriguing line:

Singleton, 25, is in major league spring training as a non-roster invitee. Under the terms of the controversial five-year extension he signed in June 2014, the left-handed hitting first baseman will make $2 million this season despite no longer being on the major league roster. 

So let's talk about the "controversy" surrounding the Singleton deal.

At the time the deal was signed, there was controversy. First, some background: Prior to the 2014 season, Singleton was ranked #82 in Baseball America's prospect rankings. He was ranked #57 by Baseball Prospectus, and #50 by MLB.com. This ranking is two years removed from his 2012 season in Corpus in which he - four years younger than his competition - hit .284/.396/.497.

He mainly spent 2013 between Double-A and Triple-A, missing 50 games due to the now-famous suspension for marijuana. Still, in the linked write-up, ESPN's Jerry Crasnick's lede described Singleton as "a rising star in the organization and the team's first baseman of the future." It was a blip, right? His numbers suffered in 2013 after the suspension, which followed a month-long stay in a rehab facility, hitting .230/.351/.401. As time went on, though, Singleton got better. After cratering in July 2013 (.178/.274/.300), he finished strong to end the 2013 season. From July 31 to the end of the minor-league season Singleton hit .268/.398/.400 - signaling, to me (and maybe others, who knows) that his eye was there, the hit tool and power would soon follow. But there was still work to be done.

Singleton described his journey in March 2014, three months before his extension and subsequent call-up:
At this point, it's pretty evident to me that I'm a drug addict. I don't openly tell everyone that, but it's pretty apparent to myself. I know that I enjoy smoking weed, I enjoy being high, and I can't block that out of my mind that I enjoy that. So I have to work against that.

The deal with the Phillies for Hunter Pence was considered a slam-dunk for the Astros, given Singleton, Cosart, and Domingo Santana's inclusion. Josh Zeid is secondary to the argument. Singleton had a hiccup with the 50-game suspension, but certainly seemed to overcome it in early 2014. Singleton opened the 2014 season with something to prove. When Singleton got called up to Houston - after signing his extension - he was hitting .267/.397/.544. At Triple-A. In his Age 22 season. Half of his hits were for extra-bases.

And so the Astros offered Singleton a deal he, apparently, could not refuse. The guaranteed deal was for 5yrs/$10m. The incentives included in the deal could push it to $35m. It was the first long-term extension for a player with no Major-League experience in baseball history.

But was it controversial?

It didn't sit well around the league. Noted Red-Ass Bud Norris - who didn't play for the Astros at that point - was decidedly not happy.
Wish the (sic) Jon listened to the union and not his agent. 

His agent, Matt Sosnick (the subject of a very good book by Jerry Crasnick), also came under fire from another agent, who told Chris Cotillo:
Sosnick is always looking to lock players up to protect himself so his players can't leave. Not in the best interest of the players.

And: Other agents really hate this deal for Singleton, who is repped by Matt Sosnick. "Disaster deal," one said.

So...the "controversy" seems to lie in Singleton leveraging long-term earnings for security. Beyond The Box Score wrote:
This new contract doesn't pay Jon Singleton much more than he'd make with reasonable arbitration predictions, and it pays him little enough that the team will squeeze lots of surplus value out of the guy - potentially by a large amount. If Jon Singleton is a star, then this will be an Evan Longoria/Mike Trout type of steal. If Jon Singleton is another Ike Davis, then this was still probably a great move by the Astros. 

FanGraphs wrote:
It goes without saying that this deal is a huge potential boon to the Astros. If Singleton turns out to be a quality player, he would have gone well beyond $35 million in his arbitration years and first free agent season, but if Singleton busts, they're only out $7 or $8 million above and beyond what they would have paid by going year to year. 

Both sides have benefited from the Singleton deal. Singleton has made $5.5m to date, and will get $2m in 2017 and 2018, with a $500,000 buyout in 2019. That amount of money is guaranteed. He won't be arbitration-eligible until 2019. So the Astros essentially gave him $9.5m for his pre-arbitration years with $20.5m for three arbitration years. He just has guaranteed money in the bank as opposed to going year-to-year. 

Let's also remember the time frame in which the Astros and Singleton signed the deal: They were coming off three straight 100+ loss seasons, including a 2013 that saw 111 losses. It was rock bottom. Yet the Astros had a plan. Let's not forget the reports that the Astros and Dominguez were close on a 5yr/$17m deal at the same time. Three months before signing Singleton, Ken Rosenthal broke that the Astros had offered George Springer a 7yr/$23m deal that would have bought out his arbitration years and one year of free agency. 

Had all three players (Singleton, Dominguez, and Springer) taken their respective deals, only the Springer deal would look like a win. Even with Springer's $3.9m salary in 2017 he will have "only" made just over $5m through his first three seasons. Springer is on track to eclipse the Astros' 2013 offer, but will need $18m over the next four years to do it. 

Rosenthal was critical of the Astros despite Chris Archer and Yan Gomes signing virtually the same deal with the Rays and Indians, respectively. Archer's deal was "the most guaranteed money" given to a player with less than a year of service time. Fox Sports' Joe Reedy said the Gomes deal was a "win-win for both sides." It was two months before the Singleton deal.

If Singleton never plays in Houston again, he will have received $10m for 420 Major-League plate appearances (no, seriously) with a .171/.290/.331 slash line. No chance he gets $10m in arbitration for that. And there's no amount of league minimum to get to $10m. Singleton won. The Astros were identifying young players to lock up for the next phase of their rebuild. Both sides assume risk: the player, again, gets immediate financial security at the expense of making more in arbitration. The team is giving guaranteed money to unproven players. That's not controversial, it's just a gamble. The "controversy" lies simply in that it was the Astros. 

Note: This post gets a massive assist from the invaluable Astros Twitter follow @BigTKirk , who asked the question about how controversial Singleton's deal actually was.