The New York Yankees have not faced such terrible conditions since 2013. While they have not won the World Series since 2009, the team has not looked as far away from it as it does right now. With an abject 82-80 season, the Bronx Bombers barely managed to cling on to a winning record, missing the playoffs for the first time since 2016. Something similar happened in 2013 when Hal Steinbrenner decided to shake things up. Can a decade’s worth of difference set the blueprint for the present?

The owner Hal Steinbrenner and GM Brian Cashman are under intense fan scrutiny. With complaints reaching the fever pitch, Steinbrenner may have to resort to big actions in the offseason as he has done before. Could history repeat itself? Will Steinbrenner open his huge checkbook for the 27-time World Champions?

Steinbrenner’s past spending sprees for New York Yankees

Hal Steinbrenner took over the management of the Yankees in 2007. Initially, he spent time just fine-tuning the system but he first showed his capacity for big spending in 2009. Seen as a way to give his father “The Boss” George Steinbrenner a fitting swansong, he bought stars like CC Sabathia and created a World Series-winning team. This form wasn’t seen again until 2013, when the Yankees were down in the dumps.

The club finished 2013 with 85-77 and failed to qualify for the playoffs. This was a major problem for a team that until then was one of the mainstays of October. Major changes were in order, so Steinbrenner whipped out his checkbook and signed players like Brian McCann for  5 years at $85 million, and Jacoby Ellsbury for 7 years at $153 million. But the biggest signing was Masahiro Tanaka for 7 years at $155 million. There were a few more signings as the Yankees spent big to improve themselves. However, in 2014 they ended the season win one win less and again failed to reach the playoffs.

2014 also was the final season of their captain Derek Jeter, so this spending had another reason. To give Jeter a fitting send-off was the dream, but unfortunately, that couldn’t happen. Now in 2023, the Bronx Bombers find themselves once again at the exact same crossroads. They have missed the playoffs but more importantly, have had their worst season since 1992, a new low in Steinbrenner and Cashman’s tenure. Is it time for the owner to empty his pockets again?

Fans believe that things have changed since 2013-14. While Steinbrenner then didn’t really care about luxury taxes, he cares now. In his bid to be more financially responsible, he has ceased to take part in big indulgent negotiations. Though the Yankees have made large signings like Gerrit Cole in 2019, they have failed to seriously pursue game-changers like Bryce Harper and Corey Seager. But if the Yankees do decide to repeat the 2014 offseason, which players could they target next?

Where could the deep Yankee funds come into use?

The obvious name would be Shohei Ohtani. The biggest free agent in the sports would be an excellent signing for the Pinstripes. Though their chances seem slim due to Ohtani’s dislike for pitching in the Yankee Stadium. But the Bronx Bombers just looking like serious contenders could give the fans a picture that the management is trying to frame. The other big name is Juan Soto, highly suitable for the Yankees system. Could they bring him on for one year until he becomes a free agent next year?

Read more: Yankees’ Non-Tender Surprise: Albert Abreu Released, and More

They can definitely go after Yoshinobu Yamamoto or their former ace Jordan Montgomery just to get genuine game-changers on their roster. Cody Bellinger could fill their left-handed hitter and outfielder shortage. Clearly, the options are many, with quite a few players still left to mention. But it is up to Hal Steinbrenner – will he spend big or will the Yankees go home again empty-handed?

Watch this Story: Could Cody Bellinger’s Yankees Roots Influence His Free Agency Fate?