It's time for the Yankees to start thinking about long-term deals for Michael Pineda and Nathan Eovaldi

The Yankees are thought of as an older team, and for the most part they are. We've witnessed the highs and lows of counting on big time contributions from players at the tail end of their careers, riding the waves of Mark Teixeira, Alex Rodriguez and Carlos Beltran all year. One spot where the roster's anything but old, though, is starting pitching. 118 of the team's 149 games thus far have been started by a pitcher aged 28 or younger. According to fWAR, the two top pitching contributors have been 26-year-old Michael Pineda and 25-year-old Nathan Eovaldi. Both will be heading into their second year of arbitration eligibility this winter and both are scheduled to reach free agency following the 2017 season.

A popular misnomer is that the Yankees have a policy against signing players to long-term contracts before they're free agents. That policy does exist for players under guaranteed contract, as Robinson Cano was when they didn't negotiate with him before the 2013-14 off-season, but the team has occasionally extended arbitration eligible talent with some pretty fantastic results. Brett Gardner has four years left on his current deal at a sub-market $50 million thanks to a savvy extension worked out in February, 2014. Cano's original contract, signed prior to his first arbitration year, paid him a team-friendly $57 million over six prime seasons. Going back a little farther, Derek Jeter's ten-year, $189 million pact agreed to during his final pre-free agent off-season made him the second highest paid player in baseball at the time, but it proved reasonable over time as salaries continued to grow.

For Pineda and Eovaldi, this fall would be a great time to act, assuming Eovaldi's current elbow inflammation issue doesn't turn into something more serious. Injury notwithstanding, Eovaldi had looked like the crown jewel of Brian Cashman's latest winter haul, especially after the All-Star break when he posted a 3.11 FIP and 7.99 strikeout rate in nine starts. Utilizing a developing splitter to curb his dependence on a high-90's, but often flat four-seamer, he posted career bests this year in ground ball rate (52.2 percent), strikeouts-per-nine (7.06) and homers-per-nine (0.58). His evolving keep the ball on the ground approach makes him a nice long-term fit for Yankee Stadium. Pineda missed most of August with a forearm strain, but has a 3.31 FIP and a 6.71 strikeout-to-walk ratio over 24 starts. A as a high BABIP and some long ball problems have kept his ERA over 4.00 he's been arguably the Yankees' most valuable pitcher from start to finish.

Two years out from free agency, we're well past the point of signing either of these guys to a highway robbery type contract like those we see around baseball for Madison Bumgarner and Chris Sale. To score that kind of win, you need to buy out pre-arbitration, league minimum years, too, which the Yankees couldn't do with Pineda still rehabbing from shoulder reconstruction and Eovaldi on the Marlins. Still, since Pineda and Eovaldi aren't yet established as front line starters, the Yankees would get a better deal now than if they wait another year and watch them get better. In the final arbitration year, long-term contracts start to look a lot like they do for free agents. Guys who are far from aces, like Homer Bailey and Rick Porcello, have landed close to or more than $100 million. Pineda and Eovaldi are both headed in that direction, and if they get there, there's a good chance one or both will be pitching somewhere else in 2018.
The other great advantage of signing guys early is it changes the years you're buying. Pineda and Eovaldi are set to be rare under-30 free agents if they get there, but if the Yankees extended them now they'd be paying for prime years and prime years only. A seven-year deal signed this off-season - more likely five with a couple of team or vesting options - would cover Pineda for ages 27 through 33 and Eovaldi for 26 through 32. You don't get that on the free agent market, where bringing in someone significant usually means keeping him into his late 30's.

Signing players, especially pitchers, early obviously doesn't come without risk, which is why the Yankees have been historically reluctant to partake. Bailey's made only 25 starts since re-upping for six years and $105 mil with Cincinnati. His remaining money is a big reason why the Reds couldn't keep Johnny Cueto and why they'll probably trade Aroldis Chapman, too. Porcello has looked better of late, but if the Red Sox had let him go free agent, he'd be worth a lot less than the $82.5 million he's owed between 2016 and 2019, especially in a crowded pitching market. There are red flags on both Pineda's and Eovaldi's masts that question the wisdom of extending either. Pineda's still yet to fashion a 30-start season or fully conquer the injury woes after pitching just 13 games between 2012 and 2014. Post-surgery, he's never recaptured the elite fastball velocity he flashed with Seattle in 2011. Eovaldi, for all the improvement Larry Rothschild's been able to coax from him, still struggles with efficiency, averaging only 5.7 innings per start this year and failing to complete the sixth in more than half. As a Tommy John survivor, an elbow-related shutdown is a real cause for concern.

Those risks, though, are what would keep the price down and potentially set the Yankees up with two rotation spots filled long-term for non-crazy money. Again, assuming his elbow checks out, Eovaldi seems like the safer bet but Pineda's probably the greater asset if everything goes well. Regardless of which you prefer, these are two players who've shown clear signs of trending upward. The Yankees should be proactive in making sure that climb takes place in New York.