Why are the Yankees so afraid of trying to buy another World Series?


CC Sabathia, Mark Teixeira, and AJ Burnett hold a special place in Yankee history.


Within three weeks, the Yankees had signed these three influential players: a bona fide ace, a good hitter to No. 3 in the standings, and a No. 2 starter to complement the ace.

All that happened after that was 103 victories and a world championship title. The front office threw caution to the wind and spent its money trying to become the best team in the league. Their dream came true, and since then, the team has seemed dead set on never doing it again.

Of course, there have been other agent signings since that winter (Russell Martin, Hirooki Kuroda, Masahiro Tanaka, DJ LeMahieu, etc.) but none of them have made a direct impact or demonstrated the kind of financial enthusiasm that led directly to the 2009 championship. It was the closest comparison to Sabathia’s championship. -Teixeira-Burnett is signing Gerrit Cole ahead of the 2020 season, which was certainly considered a cannonball-sized splash, but it was only for one player. As a rudderless team in Anaheim will tell you, no player automatically equals postseason success.

Cole and the rest of his teammates are still pulling away in their World Championship debut, and their C-suite bosses could do more to smooth that path. Every fanbase outside of Queens and San Diego can make a legitimate wrench that their team should go after free agents a little harder, but the weird part of this particular situation is that we’re talking about the New York Yankees. What used to be filmed first, ask questions later turned into checking spreadsheets first, losing in the playoffs later.

For most clubs, the Yankees’ recent run will be a godsend. This team, after all, has won 90 games in each of the last five full seasons and made the playoffs six times in a row. But their record in American League Championship games is 5-12, all at the hands of the Houston Astros, who have dealt the Yankees more than that, they’ve rounded them up and thrown them overboard.


One can certainly make the argument that paying $360 million to keep Aaron Judge and then giving $162 million to Carlos Rodon counts as “going for it.” But compared to the Mets, who handed over two $100 million contracts to the Prepared they own menplus another $197 million for Justin Verlander, Koday Singha, Jose Quintana, and David Robertson, the Yankees look just shy.

No rational person would say the Yankees were bad. But they have every right to say that it is a little confusing. As things stand now, the Yankees still have a gaping hole in left field. If the season starts tomorrow, the spot will go to Oswaldo Cabrera, who is not a natural fielder and has only played four games in the outfield during his minor league career.

CC Sabathia

Left field would have been an ideal spot to put Brandon Nemo, Andrew Benintendi, or any of the other free agent players who have since signed elsewhere. Presumably, the mall is where the Yankees will tackle this problem (Brian Reynolds, Max Kepler, and Michael A. Taylor all keep the rumors going), but that means giving up actual humans who could one day contribute to winning baseball, rather than just Give away the money they can earn fairly quickly. If this money-saving approach doesn’t lead to a championship, fans can at least rest easy knowing the Steinbrenners can still pay their mortgage.

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Pencil Case Express


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“In the end, the owner has to take everything into consideration,” Brian Cashman said at his home. End of season eulogy on November 4th. “It involves a lot of different categories. You want a team that competes for a championship and wins the championship…but in the end Hal Steinbrenner is going to gather all the information from an industry standpoint. When people are in free agency, things can get pretty crazy.”

Things have definitely gotten crazy, as many of the contracts awarded this season live in the neighborhood of nine figures. When asked about throwing money during the November press conference, Cashman alluded to the fact that ownership controls these decisions.

“Obviously you take into account everything else that isn’t baseball. What drives our fan base?” [Hal] He wants to make them happy. He’s always been driven that way, to try to make our fans happy. Hopefully we can have some positive conversations that lead to the outcome we want. But, we’ll see.”

Heading into the new year, it seems as though fans are happy with the team sticking with Judge and courting Rodon, but it’s hard to definitively say Steinbrenner has made them happy. While that’s often the case with Yankee fans, who don’t really look happy unless their players are wearing rings, these last two seasons haven’t been short on star power, and it’s been hard to see the Yankees mostly abstain.

While they entered the offseason with big financial commitments to Cole and Giancarlo Stanton, and they’ve now added Judge and Rodon’s new contracts to the ledger, they’re still nowhere close to winning. Projected Mets payroll. Part of it is because the Mets have broken all the traditional spending benchmarks, but part of it is also because the Mets have prioritized winning above all else. And this is the part where Steinbrenner has to listen closely, and doing so also means crowd pleaser! Obviously, there is no guarantee that the Yankees acquiring Nimmo or re-promoting Benintendi would have led to the Cup, and they probably didn’t even want to be Yankees anyway.

What we do know is that the last time the Yankees tried to buy a World Series, it worked. It’s been thirteen years since Sabathia, Teixeira, and Burnett were the centerpieces of Ribbon bar paradeand the Yankees have not been part of one since.

It sure looks like they should try again. They can certainly afford it.

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