It doesn’t seem like very long ago when the Yankees were about to play Game 7 of the ALCS in Houston. They had the baby bombers leading the way into a new era, a handful of grizzled vets that created arguably the best clubhouse environment in the bigs, a gimmick that stemmed from a salty Mets fan, and a lot to prove. There have been many faces that have come and gone during that time, but the core has pretty much stayed the same. Chapman, Green, Montgomery, Severino, Sanchez, Gardner, Hicks, and Judge are what remains and on paper, that seems awesome. But looking back from the year 2021, its been all downhill since Altuve’s homerun landed in the left field stands.

The Yankees’ 2021 season has been discussed, dissected, and criticized ad nauseam so I won’t be discussing just how they got to this point but what they should do now to turn the page and move on. There has to be changes made. Some changes you might agree with; some you may not. Changes you’ll welcome; changes that will make you feel sick. Regardless, these changes are necessary for the immediate and far off future of this organization.

First and foremost, the Yankees need to be sellers at the deadline and in the offseason. I see too many people saying “the Yankees should never be sellers” and “they just need Story/Gallo/Scherzer/Marte/etc”. The Yankees have a deep rooted issue within the organization that no one player from another team can come in and fix. Is Story supposed to come to New York and teach everyone how to run the bases? Is Marte coming in to show everyone how to hit for average and put the bat on the ball? Plus, do you really believe that Steinbrenner is going to add a significant piece when he’s explicitly said they will not exceed the luxury tax and they have less than $1m to play with while the team is on pace to only win 84 games? Trust me, I think it’s fucking stupid that the Yankees care about the luxury tax at all but if that’s the hand you’re dealt then you have to work with it.

Now, let’s get to the juicy part. This is who the Yankees should trade and when:

• Gary Sanchez – Now
  Gary’s value hasn’t been this high since 2019. He’s on a 30HR pace and has stayed relatively healthy. If another team is looking for a DH and/or a part-time catcher, he would be the perfect fit. Plus, he will be a free agent after 2022 and Gary is 100% going to be a full-time DH in the near future.
• Aroldis Chapman – Now
  This would be a harder sell since he picked the worst time to go into a really bad skid. However, he had only given up 1 run going into June, while debuting a new splitter that is unfair if you are looking fastball. In his last 6 appearances (6IP), he’s only given up 1 run while striking out 11. If the Yankees eat half of his contract, there will be a buyer out there for sure.
• Chad Green – Now or in the offseason
  Personally, this one would hurt the most. He has been nothing but reliable in big spots and has shown that he can overcome adversity and fix mechanical issues. He has one more year of arbitration before he becomes a free agent. He would net a big return for a team desperate for a cheap, high leverage arm but Cashman can afford to wait this one out until the offseason.
• Luke Voit – Offseason
  To be honest, they should’ve traded him last offseason. Hindsight is 20/20, but it doesn’t take an expert to see that his trade value was the highest it was ever going to be after he was crowned Home Run King* in 2020. Now that he’s been hurt for most of this season, that value has all but withered away. Hopefully, he can come back and be productive in August/September so that teams will make offers knowing that he still has 3 more years of arbitration.
• Gio Urshela – Now or in the offseason
  I’m still on the fence about this one. On one side, he’s a wizard in the hot corner, a great hitter that really balances out the lineup, and still has 2 more years left of arbitration. On the other side, teams value that too and would be willing to give up a considerable amount to add him. It all depends on the upcoming 3B market.
• Aaron Judge – Now but preferably in the offseason
  Yes, Aaron Judge. Don’t get me wrong, I want Judge to stay healthy, win awards, and get a ring with the Yankees. However, I also have to be rational and explore the possibility that that might not happen. With Judge’s extensive injury history and him turning 30 next year, he’s on the same path that his teammate Stanton is on which is not even sniffing the outfield. To give Aaron Judge a long term deal would cause a clog in the DH role when he and Stanton are in their mid to late-30s. Let another team take the gamble and if works out, then good for them. Also, it goes without saying that there would be a HUGE return for Judge. From a business perspective, it would make more sense to trade him in the offseason so that the news can break and not immediately affect ticket sales and TV ratings. It would also give them some time to take down the Judge’s Chambers and let fans mourn a little bit.
  

Those are the big 6 that yield the most return and benefit for the Yankees. There are more that I wouldn’t mind seeing get traded but I was trying to stay as realistic as possible. If those trades are made, the Yankees have the depth to cover those positions until they can bring in more talent. If they trade Gary, Higgy and Brantly will fill in. If they trade Chapman, Zack Britton can fill in the closer role as he is no stranger to it. If they trade Gio and Voit in the offseason, they can move DJ to 1B, Gleyber to 2B, put Andujar back at 3B, and sign a SS from the upcoming stacked free agent class. If they trade Judge, it opens up the field for Cashman to sign outfielders as he pleases assuming Hicks is going to take the role of 4th outfielder. All of those guys I mentioned will be missed but they aren’t irreplaceable.

Next change I would make would be to move on from Aaron Boone. I can write a 10 page paper on why Boone should not be the manager of the New York Yankees but I think most of the reasons are pretty obvious. I would say to get rid of Cashman as well but that argument is moot. Boone has shown time and time again that he is not a good in-game manager. He simply makes the wrong decisions when dealing with the bullpen, lineup construction, and ‘scheduled’ off days. It’s clear when he goes up against good in-game managers like Alex Cora and AJ Hinch that Boone has no real idea of what he’s doing. His statements to the media are laughable at this point and have consistently been the thing to look forward to after devastating losses. Perhaps next time, the Yankees will hire someone who has actually had coaching/managerial experience rather than a broadcast commentator who hit a walk-off homerun in the playoffs this one time.

At the time of writing this, the Yankees are 51-47 which means there are only 64 games to go. They are currently 9 games back from 1st place in the AL East (and 8 GB from the 2nd place Rays). They only play Boston and the Rays 6 more times each meaning that if they win every game against those two teams from here on out, it would not be enough to catch up them. If the Yankees want to make the playoffs at all, the second Wild Card spot is their best chance. The Oakland Athletics currently hold that spot with a 56-45 record meaning the Yanks are only 3.5 games behind. Doesn’t seem like that hard of a mountain to climb especially when they play each other in a 4 game set at the end of August. However, let me put this in another perspective. Oakland has a .554 win percentage so far this season which means they will win at least 89 games if they keep their current pace. The Yankees have 51 wins and will need to reach 90 if they want that Wild Card spot. Basically, they will have to win 39 out of their next 64 games resulting in a .609 winning percentage which is the current winning percentage of Boston and Houston, the best teams in the AL. In conclusion, the Yankees will have to be the best team in the AL for the rest of the season just to nab that second Wild Card spot where they would have to go to Tampa and play the Rays. To trade prospects for rentals just to have a chance at that is not worth it in my opinion.

Now that I’ve said all of that, I fully expect the Yankees to acquire some guys at the deadline that will ultimately result in them making the playoffs, but not even sniffing the World Series. I have no reason to believe Brian Cashman and the rest of the front office are switching things up. From a business standpoint, things couldn’t be better. They sell Judge and Cole jerseys like crazy, TV ratings have been really good the last few years, attendance has been solid, and making the playoffs doesn’t hurt the bank. Look out for the Yanks to make a few minor moves and one ‘big’ move that gets the fans excited at the deadline.