Looking down the road, the Yankees will need to start extending some key players before they hit unrestricted free agency -- waters that those players might want to navigate to find a new team.
So, while the Yankees have a roster capable of winning a World Series at the moment, GM Brian Cashman will be doing everything in his power to make sure that remains intact. To do so, it requires some big decisions.
Let's take a look at players the Yankees could consider giving a new contract to, starting with C Gary Sanchez...
CONTRACT: Agreed to one-year, $5 million deal before hitting arbitration in 2020. He is arbitration-eligible for the next two seasons.
Why should Sanchez stay?
When healthy -- that's the key factor -- Sanchez is one of the best catchers in the game. There's a reason Cashman repeatedly said no to teams trying to poach him via trade.
"The Kraken" has a very solid bat, and that showed in his first All-Star season in 2017 when he slashed .278/.345/.531 with 33 homers and 90 RBI over 122 games. These last two seasons have seen injuries hurt his numbers a bit, but he is still a big threat at the plate. And when he gets going on a hot streak, there's literally no stopping him.
For as much criticism as he gets on his defense, Sanchez does have one of the best pop times in the league. His cannon arm is a true asset against teams trying to steal bases, and he isn't scared to snap throws back to bags to keep runners honest.
Sanchez has his flaws, but he'll be 27 years old with a lot of baseball left ahead of him. If he focuses on remaining healthy, his power bat and arm should keep him in the catcher's role for years to come.
Why should Sanchez go?
Inconsistency has been a theme for "El Gary" of late. Those injuries have led to spotty play, with his woeful .186 average over 89 games in 2018 when he just couldn't stay on the field. And in 106 games last season, he had a .232 average, though he notched a career-high with 34 homers.
But it isn't the bat that the Yankees are worried about. There is no trust with Sanchez behind the plate despite his extra practice in the offseason and during the year to get better in that department. Whether it's simply laziness on balls in the dirt or getting mixed up with pitchers, there have been too many times Sanchez' errors at the plate cost the Yankees. It should be something to consider when extension talks get brought up.
Also, Sanchez hasn't had the knack for the big moments in the postseason. He is a career .176/.225/.382 hitter with 16 RBI and six home runs over 27 games. Yankees fans probably haven't forgetten his 12 strikeouts in the ALCS against the Astros last season -- he has 40 total strikeouts in his postseason career.
Mind you, this is Sanchez in his prime. So does he really deserve a big extension when history shows things start to go downhill?
What's the right move?
This will be a very tough choice for Cashman no matter what happens. He was the first Baby Bomber to burst onto the scene in 2016 and almost win Rookie of the Year despite only playing 59 games. Yankees fans haven't seen that Sanchez since, though, and having his type of injury history is never good when looking at a big-money deal.
So the right move would be this: Since he has two years left of arbitration, see if you can get Sanchez to agree to a long-term extension now at a lower rate than what he might get once he hits free agency in 2023. The Yankees have already done that with Luis Severino and Aaron Hicks, giving them their guaranteed money now and ultimately saving the Yankees money down the road.
Sanchez is a great ballplayer with natural, raw power that you can't just pick up on the free agent market. His defense definitely needs to get better, and postseason success needs to come because this Yankees team will be in that position at least in the short-term.
But if Sanchez doesn't want to take that guaranteed money early and continues to show mediocre results on the field, Cashman should bite the bullet and let him try to find a bigger deal in free agency three seasons from now. The educated guess would say the money he'd be looking for won't be worth it in the long run.