3 reminders that long extensions for young players are still risky

It’s hard to remember now, but there was a point when White Sox fans were excited about their team this year. They bought a closer. They bought a leftfielder. They traded for a pricey pitcher in the last year of his deal. They saw some wiggle room in the payroll and they pounced. We’ll have a long time to figure out if it was a good plan, but for a couple months, at least, it felt like one. And it was all because of Chris Sale.

It wasn’t that Sale was one of the best pitchers in baseball (he is) and that he’s worth building around (also true). It’s that he’s a bargain -- an absolute bargain -- and he allowed the White Sox to have that financial flexibility. Sale signed his six-year extension the spring after he missed time with shoulder fatigue, before his first 200-inning season. He got security. The White Sox got cost certainty. Everyone was a winner. Except for the actual White Sox when they played baseball games, but that’s not Sale’s fault. Because the White Sox didn’t have to worry about paying ace money to their ace, they got to have an exciting offseason.

This is why it’s so easy to laud the huge, speculative extensions for young, burgeoning stars. The Giants did the same thing with Madison Bumgarner, and it’s why they can keep re-signing their own players. The Royals did it with Salvador Perez, and it’s why they could add hitters like Kendrys Morales and Alex Rios in the offseason. All hail the proactive extensions!

Except, there’s a dark side. There’s a reason why players are willing to give up the potential of a nine-figure deal to guarantee they’ll get eight figures. Sometimes, the mountain path to stardom is blocked by a very kicky goat. Here are the tales of four contract extensions that did not work out, an idea prompted by ...

That guy. One of my first articles for SB Nation was a laudatory paean to Cahill’s sinker. It featured this GIF:

The pitch moved. It dove and darted, slid and snapped. Cahill was just 23 when he signed his extension, and he was coming off an MLB All-Star season. He was going to sink his way into the A’s hearts for years and years. Instead, he became a living reminder that pitchers don’t always progress in a nice, linear way. Sometimes, they’ll peak in their early 20s, when their arm is fresh. Cahill went from a burgeoning start to an innings eater to a liability to a baseball vagabond. His partnership with the Braves was inspiring, because if any team could fix him, the Braves had to be at the top of the list.

Instead, Cahill was designated for assignment after just two months. And it’s not like the Braves were taking a flier on him -- they were responsible for $5.5 million of his contract this season. He wasn’t a cheap raffle ticket; he was a substantial wager at the roulette table. And it’s hard to figure out why he fell so far, so fast.

It’s not velocity. He’s throwing as hard as ever. It’s not the movement. The sinker still has absurd sink. It’s not that he’s grooving more pitches. He actually threw fewer pitches in the middle of the zone than he did in his All-Star season.

It’s the control and/or command that’s getting him, but there’s no explicit reason why his control should be failing him so much. Mechanics? Fatigue? Athleticism? No idea. But for every Sale, there seems to be a Cahill or a ...

The Blue Jays have paid Romero $15 million since his last win for them. It wasn’t supposed to be like this. He had one of the better, sillier nicknames in baseball (RR Cool Jay!), and he was going to be a Blue Jays ace for years to come. He had Cahill’s progression in reverse, beginning his career as an average innings eater, then steadily moving up the ladder to be the rightful Opening Day starter. He was a part of the legendary 2005 draft, and he was one of the reasons it was such a bounty of talent.

Look at that draft. Tulowitzki, McCutchen, Braun, Romero, Upton, Gordon ... look at that danged draft.

He fit with those names. He fit so well. And just like Cahill, there’s no satisfactory explanation of what happened. Romero became one of the wildest pitchers in baseball without warning, and no one ever figured out why. There was no reduced velocity (like with Tim Lincecum) or nasty injury (like with dozens of other pitchers). There was just ... no more Ricky Romero. The progression was the same as it will always be, moving from “what’s wrong with this pitcher?” discussions to the vast emptiness of “oh, yeah, I forgot about that guy” far too quickly.

Romero was supposed to allow the Jays to have an offseason like the White Sox enjoyed. The luxury of a low-cost ace was supposed to make it reasonable to pay market price for a complementary player. Instead, the Jays had to make do with their expensive, under-performing rotation and hope that they got lucky. With a couple of pitchers like the 2011 version of Romero, the Blue Jays might be eight games up in the AL East. Instead, they lost that guy and then they lost the flexibility to get the right reinforcement, too.

But it’s not all pitchers who mess up the art of the long-term deal. There’s also guys like ...

He was a 24-year-old rookie middle infielder who hit 23 homers while playing half his games in Petco Park. How do you not want to lock that guy up? The only real question is when to stop offering him more and more years on the extension. He had a 113 OPS+ when he was 24, which meant it was reasonable to expect even more from him as he entered his prime, and that even more would mean he would be a perennial All-Star.

Instead, he was one of the worst everyday players in baseball last year, hitting .210/.280/.333. He’s hitting .210 again this year, and he’s doing it with even less power. There was a glimmer of hope last year, as Gyorko got relatively hot after the All-Star break, but he lost his job to Cory Spangenberg this season and was banished to the minors again. He’s 26 now, and he’s been a .220-or-worse hitter for almost two calendar years now. He’ll make $13 million in 2019, which is an absolutely stunning amount for a player struggling this mightily.

Even when the problem with a pitcher is hard to diagnose, like with Cahill and Romero, there’s still an element of assumed risk that’s easy to understand because pitchers are supposed to be fragile and mercurial. Gyorko reminds us that hitters can be just as weird, and considering how far removed we are from the version the Padres thought they were locking up, it looks like the problem had more to do with poor evaluation and overreacting to a fast start. It’s the new front office regime that has to pay for it, too.

Jaime Garcia pitched just 16 games of dubious quality in the two seasons after his contract extension, but he’s throwing well for a thriving Cardinals team that needs him. Matt Moore might be the best deadline addition any team will make this year. Derek Holland still has a year to make good on his extension, and Matt Harrison is pitching again and throwing his fastball in the low-90s. All of them (except Moore) could have been included in this article, but there’s still a chance their teams will be very glad they have them around, even if it comes at a premium.

Still, it’s not all Chris Sales and Madison Bumgarners when it comes to proactive contract extensions. It’s very, very easy to slobber over a below-market deal when the terms are announced because it’s not hard to project the wild offseasons of the future made possible by the savings, but there’s a reason why young kids continue to give up their chance for an early $100 million payday. It’s just hard to remember that when the deal’s announced and the players are still young and filled with unlimited potential.

Sorry to get all maudlin on you. Go hug a young player.