In 2014, the Houston Astros made history by signing Jonathan Singleton to a contract extension: he was the first player with no Big League service time to sign such an agreement. The deal was a five year contract worth $10 million that included three option years that could net Singleton up to $20 million dollars on top of his guaranteed money.
The deal garnered its share of criticism. Pitcher Bud Norris called the deal "terrible", noting he wished Singleton "listened to the (Players') union and not his agent". Norris isn't exactly known for his economic prowess or for having good opinions, but he's not completely wrong. Former Oakland A's great Mark Mulder also weighed in on the deal, saying Singleton either "doesn't believe in himself to be great or he has a terrible agent who wants the 4%". Seems like an odd thing to say for a guy who was forced out of the league due to injury, but he's Mark Mulder so we'll allow it. Norris can screw right off, though.
Mulder and Norris weren't wrong in theory - should Singleton be an above average baseball player, something the Astros and prospect gurus thought he would be, he'd be missing out on millions he could have earned if he had gone through arbitration and reached free agency. They're wrong in judging Singleton for making his own choice, one that looks shrewd through our hindsight microscope. He's still in the minor leagues after a few bitter cups of big league coffee, looking more and more like a prospect flameout. He won't turn 25 until later this year so there's time for him to recoup, but as of now, it looks he made a smart decision.
All of that is a long introduction to the idea of giving Sean Manaea a similar type deal. Manaea is a different case, of course. He's already made his big league debut. He's a pitcher and a left handed one at that, and his place in the league is more secure than Singleton's just by virtue of position and handedness. His health is probably less a certainty than Singleton's as pitchers' arms are subject to spontaneous combustion from time to time.
Would Manaea go for a guaranteed contract?
As my username will indicate, I am not Sean Manaea so this question is a touch above my pay-grade.
Manaea is riding a nice stretch of health (knocks on wood vigorously), but had his share of issues prior to joining the A's. Injuries are typically the impetus for quality players signing team friendly deals, doing so guarantees payment in the event their career is shortened by injury. It's not a stretch to imagine Manaea going for the sure thing.
Of course, he would be leaving potential bucketloads of money on the table, money he could earn in arbitration or in free agency. As was the case with Singleton and Doo, deals can swing farther towards market value with the addition of incentives and option years, but there's undoubtedly less money overall in a team friendly extension.
Would the A's agree to a deal like this?
Singleton's contract is unique in its timing, but not in its nature. The A's signed a similar team friendly deal, insuring the respective player against injury just a few seasons back. Sean Doolittle's 5 year, $10.5 million contract was certainly under market value for a late inning reliever. Just a year later, Doo's career looked in jeopardy as he missed the bulk of the 2015 season with a shoulder issue. Fortunately for all of us, Doo's velocity is back and even if he's not the same reliever he was before, he's a bargain.
The A's haven't shied away from these types of deals before, and it's no wonder. They're team friendly to the point where an injury or descent into sucktitude won't inhibit future spending . The A's lack of extensions as of late is probably more a reflection of a lack of extendable players than a philosophy.