What needs to happen for the Yankees to win the World Series?

We’re now two days from the start of the ALDS, and the beginning of what will hopefully a long and fruitful campaign through October for the Yankees. The Bombers have an excellent roster and just finished off a 103-59 season, but as with any team, they’ll have to come up big when it matters most and hope that the ball bounces their way if they want to outlast the rest of a deep playoff field.

What exactly needs to happen for this squad to go all the way? What do they need to do to ensure this playoff run lasts longer than not just last year’s disappointing ALDS exit, but also 2017’s surprising ALCS effort? I asked a few of our staff writers to get a feel for what must transpire for the 2019 Yankees bring a World Series to the Bronx for the first time in a decade.

What needs to happen for the Yankees to win the World Series?

John: First off, and most importantly, the offense needs to show up, and consistently. I’m not saying they need to break out and score seven runs every game (though that would be nice), but we can’t have a situation where only Aaron Judge and Gary Sanchez have an OPS over .710 - which is what happened in the ALDS last year.

Likewise, we need to see better bullpen management from Boone compared to last year. No Chance Adams or Luis Cessa when the game is on the line in the fourth inning instead of Adam Ottavino or Tommy Kahnle.

Freeni: The Yankees have been able to hit all season, and even though they struggled a bit at season’s end. you have to acknowledge that the offense is a strength. However, starting pitching has obviously been a persistent problem. The rotation doesn’t necessarily need to go very deep into games in order for the Yankees to win the World Series, but the starting pitching does have to keep them in the game early on. The success of James Paxton, Luis Severino, and Masahiro Tanaka will be huge factors in whether or not the Yankees are able to win it all.

Aaron: Their starting staff has to prove capable of going out and providing a solid five or six innings before turning it over to their elite bullpen, but they also need the offense to provide the same support they did all season. The 2019 Yankees posted the highest slugging percentage in team history (.490), narrowly edging out the legendary 1927 Yankees (.489). However, the Yankees registered a disappointing .448 team slugging percentage over the final 11 games of the season, ranking 12th in MLB. Gleyber Torres, Gio Urshela, Luke Voit, and Didi Gregorius will need to put a disappointing month of September behind them quickly for the Yankees’ offense to carry them where they want to go.

What needs to happen for the Yankees to lose to the Twins?

John: The ALDS looks to be a hitters’ paradise, as the Yankees and Twins are #1 and #2 in the AL in runs scored, compared to #5 and #6 in runs against. Both teams’ staffs are above-average, but nowhere near as good as their lineups. So, naturally, let’s get ready for a series of pitchers’ duels.

In all seriousness, though, it’s going to come down to the Yankees’ ability to keep the Twins offense in check - I doubt they will be completely shut down - while finding ways to score off the Twins. If the bats shut down, I don’t foresee the pitching staff picking up the slack.

Freeni: I would choose the Yankees over the Twins in a pitchers’ duel or in a battle of the bullpens. I just don’t see the Twins silencing the Yankees offense under most circumstances. The only way I see the Twins beating the Yankees is if they are able to use their offense to out slug the Yankees hitters. If their pitching beats the Yankees, I’ll be surprised.

Aaron: The Yankees could very well lose in the ALDS if James Paxton falls flat on his face in his first taste of the playoffs. Paxton has been lights out for the Yankees in the second half, but his shortened outing to end the regular season has to be a concern. Paxton’s as good as anybody in baseball when he’s 100%, but nagging lower body injuries have seemingly crippled him in the past, so his performance in the ALDS could make or break the Yankees. If Paxton is the same guy who rattled off ten straight wins recently, the Yankees are going to be hard to beat. If not, they could be in trouble.

Is this the Yankees’ best chance to win a World Series with this core?

John: It’s close, but not quite. Next year, in my opinion, shapes up to be the big year. Among players that started the season with the team only Didi Gregorius and Dellin Betances profile as potentially significant free agent losses, and there must be at least one big free agent that the team could pursue to help anchor the starting rotation. As of now, although Toronto is definitely on the rise, I don’t truly fear any team in the division next year except for Tampa Bay, as Boston could be about to sink even further than they have. That said, this year is still shaping up to be one of the team’s best chances in this window of contention, what with a 103-win season and loaded roster in tow.

Freeni: I actually believe this core is still being built. The Yankees have added plenty of offense and relievers over the last couple of year, but can still improve the rotation. Coincidentally, the free-agent starting pitching pool looks strong this year. The addition of Gerrit Cole, Madison Bumgarner, or Zack Wheeler, can immediately make the rotation better. Not to mention that three of their biggest contracts due to Jacoby Ellsbury, J.A. Happ, and possibly Aroldis Chapman could be off the books with the next year or two, leaving ownership with no reasonable excuse not to spend. It’s crazy to say, but this team of studs should only getting better.

Aaron: I don’t believe this is necessarily the Yankees’ best chance to win the World Series. There’s very little reason to believe they’ll be any worse next season, and plenty of reason to believe they’ll actually be a bit better. It will almost surely suffer fewer injuries next year, and players like Gleyber Torres, Gary Sanchez, Miguel Andujar, Clint Frazier, and even Aaron Judge should still be on an upward trajectory. The Yankees aren’t at risk of losing anyone to free agency that would ruin their title chances next season, and there’s potential for them to add a front line starter, as well as improve their pitching depth internally with youngsters like Deivi Garcia and a healthy Michael King.