The New York Yankees once owned October. But now? No WS ring for 16 years. In 2024, hope flickered across the Bronx when they reached the World Series, only to watch a $162M bat crush that dream with a walk-off grand slam. This season, the Yankees secured another postseason berth, but their October story repeated itself—elimination came at the hands of the Blue Jays in the Division Series. The painful reality is this: the player who shattered their World Series dreams could have been wearing pinstripes all along.

That player is Freddie Freeman, who signed a six-year, $162 million contract with the Los Angeles Dodgers in March 2022. Before joining the Dodgers, Freeman spent 12 seasons with the Atlanta Braves, where he developed into one of baseball’s most consistent offensive forces. The Yankees had their chance to sign him following his free agency, but they chose a different path.

Stephen Parello wrote in a recent post that the Yankees’ biggest mistake was not signing Freeman and instead signing Anthony Rizzo to a two-year, $32 million deal. Parello said that in 2021, Rizzo hit .248/.344/.440 with 22 home runs for both Chicago and New York Mets, while Freeman hit .300/.393/.503 with 31 home runs. The difference was clear. Yet the clubhouse went for Rizzo.

Since joining the Dodgers, Freeman has been unstoppable. He completely dominated the 2024 World Series with 6 home runs and scored 5 runs in five games. Freeman also had 12 RBIs and was named Series MVP. The sluggers have shown that they can rise to the occasion when the lights are brightest, which makes the Yankees’ choice look bad in hindsight.

Meanwhile, the Yankees got diminishing returns from Rizzo. After a concussion in 2023 derailed his season, Rizzo posted a .228/.301/.335 slash line with just eight home runs in 2024—his worst performance since his rookie year.

Injuries limited him to 92 games before the Yankees declined his $17 million option for 2025. Rizzo announced his retirement in September 2025.

The 2025 season brought another painful reminder of this miscalculation. The Yankees lost to the Blue Jays 5-2 in Game 4 of the ALDS, getting eliminated from the playoffs and extending their championship drought to 16 years.

They remain stuck in pursuit of their 28th title, still searching for the moves that could have changed everything. The 36-year-old wasn’t just a player the Yankees missed—he was the cornerstone they needed, now flourishing with their biggest rival while they watch from home each October.

Interestingly, Freeman wasn’t the only missed chance that strengthened the Boys in Blue. There were other missteps, too!

More than just one missed bat, additional front-office missteps

The New York Yankees’ front office not only missed the opportunity to sign Freddie Freeman but also made critical mistakes that benefited the Dodgers. A key chance they overlooked was signing ace pitcher Blake Snell in the past two offseasons. According to reports, the Yankees have long been linked to Snell, but they didn’t meet his market value and chose a less expensive option instead.

Another miscalculation they made was failing to outbid the Japanese star Yoshinobu Yamamoto. The Yankees are said to have offered about $300 million, but the Dodgers countered with a 12-year, $325 million deal.

Analyst says that this unwillingness to spend a lot of money on Yamamoto gives L.A. a major edge in the rotation. And his performance in NLCS Game 2, in which he made history by throwing a postseason complete game.

That’s not all, there are more missed chances!

The Yankees missed yet another chance to steal versatile veteran Kike Hernandez from L.A. In the playoffs, he has been a game-changer for the Dodgers, hitting .282/.356/.508. Parello wrote in that same column that getting Hernandez would have taken away a vital role player weapon from the Dodgers and made New York’s team deeper.

These decisions, along with the Freeman aftermath, set a pattern: the Yankees kept missing big moves, and the Dodgers took advantage. The bigger question now is whether New York will learn and do something about it sooner rather than later.