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The Tuesday Discussion: A VERY DIFFICULT Choice

This week we jumped into the hypothetical...


If you could make this deal - would you? A guaranteed 2022 Yankees World Championship but, the price for that would be that Aaron Judge leaves at the end of the year and signs with the Mets or Red Sox.


Here are their replies...

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Tamar Chalker - Nope - I think the Yankees can build a team that wins more than two championships with Aaron Judge if they can get him to stay. I also have enough faith in their ability to win this year without a guarantee, though we all know you never know what may happen.

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Cary Greene - There's no way I'd make this deal because it seems like the Devil would be the one brokering it - guaranteeing Yankees fans a banner if only they'd be willing to give up the face of their beloved franchise to not only another team, but to arguably the two most hated rivals in franchise history.


I actually feel for Judge though because here he is, he'll be approaching 30 1/2 years before he ever gets a chance to truly test his market and explore free agency. The Yankees have extracted a whale of a profit already regarding Aaron Judge - simply due to the way the league suppresses payroll through the nuances of the CBA.

If Cashman blunders Judge away, he'll have himself to thank. It will be bittersweet if that happens and the Yankees do win a championship, but life goes on and I'm content to cross the "Judge explores Free-Agency" bridge when it happens. I'm surprised Cashman hasn't acquiesced by quietly eating-crow and making a better offer to Judge. He's kind of playing with fire on this one.

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Paul Semendinger - I love Judge. But, give me the championship. I want the championship. I'm tired of waiting for the championship, hoping the next group of players gets it.


Give me the World Series victory, and I'll take my chances that the Yankees can win in 2023 and beyond with someone else.


Of course, I want the championship and Judge, but if I can only have one, I'll take the championship.

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Lincoln Mitchell - This is a tough question because there are many unknowns. For example, what do the Yankees do with the money they don’t spend on Judge? However, for me the answer is yes. With thirty teams, an extended playoffs and so many limits on how teams can spend money to win World Series championships are much more difficult than they used to be. As good as Judge is, I could easily see him being a great player for two more years and then a good player for another two or three and then not much after that. That is if he manages to stay healthy. Also, Judge is the kind of player who I could easily dislike if he were on a rival team. Parenthetically, the Red Sox are a rival team. The Mets are just another team.

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James Vlietstra - It’s never been harder to win a World Series than it is right now. There’s 30 teams vying for 12 playoff spots, then 4 rounds of playoffs. Couple that with the Yankees worst World Series drought in almost 100 years, having only won one in the past 21 years, and I could see how a fan base would be desperate.


However, the Yankees aren’t just after one championship. Allowing Aaron Judge to leave would severely hamper their future chances. And while it’s far from a guarantee that the Yankees will win it this year, I like their chances, without selling their soul. Obviously any team can knock off another much better team at any point, but this 2022 squad has all the components to be a historically significant team.


Now on to the Judge Yankees legacy part…


Judge is exactly 20 WAR from joining the Yankees top 10, offensively. 30 from top 6 overall.

Since 2017, he’s accumulated 29.9 WAR in 608 games. That’s 1 every 20.3 games played over a 6 year span.


He’s played in 111 out of the last 127 team games over the past two years. So we no longer have to say when healthy.


Judge is the face of the Yankees. More so even the face of the sport. You don’t let players like him go, you build around them, promote a chamber in the stands, and you hope he leads you to multiple championships.


His arbitration hearing is tomorrow. If I am Cashman, I make one more last minute long term proposal for an 8 year/$310M extension on top of the $21M from this year that will be the new standard for position players.

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Mike Whiteman - I'd do it. Nothing is guaranteed on the future, and we can’t take the opportunity for a title for granted.

Along the same lines, I hope Cashman goes all-in for an impact outfield bat and pitching reinforcements at the trade deadline.

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Chris O'Connor - As much as I love Aaron Judge... this is a pretty easy decision. I would guarantee a Yankees World Series win in 2022. While Aaron Judge has been unbelievably good in 2022 and will probably win MVP, there is a limit to how much value one player can bring to a team. Mike Trout has made the playoffs once in his entire career! The Red Sox traded Mookie Betts and, after one down season, were in the ALCS last season. Of course I would like the Yankees to re-sign Judge, and they are absolutely better with him than without him. But as good as he is, they could certainly survive without him and a World Series win is the ultimate goal every season. As the Yankees have proved since their last triumph in 2009, having a great team in modern baseball is no guarantee of postseason success. The 2010-2012 and 2017-2020 teams were all good enough to win it all, but for any number of reasons could not get over the hump. With the playoff scars and experience that the 2022 Yankees have, combined with their historical dominance to start the season, this appears to be the perfect opportunity to end the World Series drought.

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Patrick Gunn - This is a classic win-now versus future question. Granted, there's technically no reason that both the Yankees could win the World Series with Judge if chosen otherwise, but that's me nitpicking. The Yankees might be in their best position to win a World Series in quite some time; even the 2019 Next Man Up Yankees had a 100+ win Astros that was healthier and had a stronger rotation to contend with. New York has seen no such obstacles in the American League - yet. It's still fairly early, the Blue Jays could morph into the juggernaut we saw in the regular season, the Red Sox could acquire more depth and pitching, the Astros could make a splash, and the Twins and Guardians could keep ascending. So, a guaranteed World Series might redeem this core in some capacity. That means being fine with whatever Judge does with the rest of his career. The outfielder has only been stopped in his career because of various injuries yet he's been healthy the past two seasons. He's even been willing to play center field a lot this year and has been available every game this season in every country. It really comes down to value, the Yankees are probably not going to find an adequate replacement for Judge's power and two-way production. Maybe they swing a trade for Juan Soto, but that would require half their farm system and Soto's not the same defender as Judge. I'd probably opt for the latter, keep Judge and go from there, with the possibility that they could still win a World Series without the guarantee and that even when missing time Judge is still one of the best outfielders in the league.

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Tim Kabel - I would not take the deal. There are a few reasons. First it says that the Yankees would be guaranteed to win the World Series but, the price would be that Aaron Judge would leave and sign with either the Mets or the Red Sox. I would rather take my chances that they win this year and have Judge back for the rest of his career.

In other words, I like the chances of the team winning the World Series without having to make a deal to guarantee it. On the other hand, if they lost, they would still be set up to win again next year. The best players on the team will all be coming back, including Judge

Judge is having an MVP caliber season end if he stays healthy, he should be able to continue at that level for several years. If he were a free agent, he would be the one the Yankees would go after. He is already a Yankee; they should keep him and continue to take their chances year after year. He is the best player the Yankees have produced since Derek Jeter and ideally, he will play his entire career as a Yankee and be the next team captain. I would not make the deal that is proposed.

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Andy Singer - I agonized over this one. I'm the same guy that's written the phrase, "Flags fly forever" in any number of posts over the last 7 years. However, I don't think we need to make a deal this extreme to bring multiple World Series flags to the Bronx. Last season, it seemed as though the Yankees' championship window was closing quickly with the current core. Right now, I'm not so sure that's true. The Yankees have a pitching staff that is built to be excellent for the next 3-5 seasons, some young players on the precipice of the Majors to pair with guys like Judge and Torres who (should both maintain their performance for at least another 2-3 years), and a development plan that should allow them to continue to feed contributors to the big league roster from the minors. I want to keep Judge around and try to build a dynasty! Plus: I don't think I could bear the sight of Judge playing for the Red Sox...I just couldn't handle it.


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