Last time the Yankees tried to buy a World Series, it worked. Why are they so scared of trying again? – The Denver Post

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The offseason of CC Sabathia, Mark Teixeira and A.J. Burnett holds a special place in Yankee history.

In the span of three weeks, the Yankees signed all three of those impactful players: a bona fide ace, a well-rounded hitter to bat third in the order, and a solid No. 2 starter to complement the ace.

All that happened after that was 103 wins and a World Series title. The front office threw caution to the wind and spent their money in an attempt to become the best team in the league. Their dream came true, and ever since then, the team has seemed dead set on never doing that ever again.

Of course, there have been other free agent signings since that winter (Russell Martin, Hiroki Kuroda, Masahiro Tanaka, DJ LeMahieu, etc.) but none had the immediate impact or showed the type of financial gusto that directly led to the 2009 championship. The closest comparison to the Sabathia-Teixeira-Burnett flurry was signing Gerrit Cole before the 2020 season, which certainly counted as a cannonball-sized splash, but it was just for one player. As the rudderless team in Anaheim will tell you, one player does not automatically equate to postseason success.

Cole and the rest of his teammates are still chipping away at their first World Series appearance, and their bosses in the C-suite could do a little more to make that path easier. Every fan base outside of Queens and San Diego can make a legitimate gripe that their team should pursue free agents harder, but the peculiar part of this particular situation is that we are talking about the literal New York Yankees. What used to be shoot first, ask questions later has transformed into a check the spreadsheets first, lose in the playoffs later.

For most clubs, the Yankees’ recent run would be a godsend. This is a team, after all, that 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 Series games is 5-12, all at the hands of the Houston Astros, who have more than handled the Yankees, they’ve packed them up and cast them out to sea.

One can definitely make the argument that shelling out $360 million to keep Aaron Judge and then giving $162 million to Carlos Rodon qualifies as a “going for it” offseason. But when compared to the Mets, who handed out two $100 million contracts to bring back their own guys, plus $197 million more for Justin Verlander, Kodai Senga, Jose Quintana and David Robertson, the Yankees look timid.

No rational person will say the Yankees had a bad offseason. But they have every right to say that it’s been a bit confusing. As things stand right now, the Yankees still have a gaping, odorous hole in left field. If the season started tomorrow the spot would go to Oswaldo Cabrera, who is not a natural outfielder and played just four games in the outfield during his minor-league career.

Left field would have been a perfect place to put Brandon Nimmo, Andrew Benintendi, or any of the other free agent outfielders who have since signed elsewhere. The trade market is supposedly where the Yankees will address this issue (Bryan Reynolds, Max Kepler and Michael A. Taylor are all keeping the rumor mill spinning), but that will mean giving up actual human beings who could one day contribute to winning baseball, rather than simply giving up money that they can earn back rather quickly. If this save-money approach doesn’t lead to a championship, at least the fans can rest easy knowing the Steinbrenners can still afford to pay their mortgage.

“Ultimately the owner has to take everything into account,” Brian Cashman said at his end-of-season eulogy on Nov. 4. “It involves a lot of different categories. You want a team that will compete for a championship and win a championship…but ultimately Hal Steinbrenner will collect all the information from an industry standpoint. Where people are in free agency, things can get pretty crazy.”

Things have definitely gotten crazy, as many of the contracts given out this offseason have lived in the nine-figure neighborhood. When asked about throwing money during that November press conference, Cashman hinted at the fact that ownership controls these decisions.

“Obviously, you factor in everything else that is not baseball related. What drives our fan base? [Hal] wants to make them happy. He’s always been driven that way, to try and make our fans happy. Hopefully, we’ll 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 pleased that the team held onto Judge and courted Rodon, but it’s hard to definitively say that Steinbrenner has made them happy. While that is often the case with Yankee fans, who don’t seem truly happy unless their players are wearing rings, these last two offseasons have not lacked for star power, and it’s been jarring to see the Yankees mostly abstain.

While they entered the offseason with major financial commitments to Cole and Giancarlo Stanton, and have now added Judge and Rodon’s new contracts to the ledger, they’re still nowhere near the Mets’ projected payroll. Part of that is because the Mets have broken all conventional spending norms, but part of it is also because the Mets have prioritized winning far above everything else. And, this is the part where Steinbrenner should listen closely, doing so means also making the fans happy! Obviously, there is no guarantee that the Yankees getting Nimmo or re-upping Benintendi would have led to a trophy, and they might not have even wanted to be a Yankee anyway.

What we do know is that the last time the Yankees tried to buy a World Series, it worked. Thirteen years have elapsed since Sabathia, Teixeira and Burnett were center pieces of a ticker tape parade, and the Yankees haven’t been part of a single one since.

It sure seems like they should try again. They can definitely afford it.

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