Yankees’ Hal Steinbrenner is tired of the awful trades

MLB: New York Yankees-Aaron Judge press conference
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The New York Yankees find themselves in a precarious position, with the pressure on them to avoid making poor trades, particularly as their highly touted prospects like Jasson Dominguez and Austin Wells begin to make their marks in the MLB. The recent sweep of the Houston Astros highlights the unexpected dividends these rookies can pay.

The front office has a small chance to sidestep a brutal next few seasons if their youngsters can rise to the occasion.

Owner Hal Steinbrenner Puts the Brakes on Trades

General Manager Brian Cashman was all set to continue wheeling and dealing as the August trade deadline approached. However, owner Hal Steinbrenner stepped in, decisively shutting down any further player movement. Steinbrenner has been less than impressed with recent acquisitions like Frankie Montas, Joey Gallo, and a financially cumbersome deal for Josh Donaldson.

“We’ll learn a lot in September and we’ll learn a lot in the spring,” Steinbrenner said while visiting the team’s minor league affiliate in Tampa, Florida (via the AP). “That’s why I didn’t want to trade these guys away at the trade deadline. We’ve traded away too many guys the last few years. So, I think it will be exciting.”

Frankie Montas: A Lesson in Poor Decision Making

Brian Cashman’s decision to trade for 30-year-old starting pitcher Frankie Montas will likely be remembered as one of his most glaring mistakes.

Acquired despite a missed shoulder injury, Montas managed a meager 6.35 ERA across 39.2 innings for the Yankees before being shut down. Initially slated for a full recovery in time for the 2024 season, Montas is now expected to miss the entire campaign due to surgery. The Yankees may look to ink a team-friendly deal with him but are likely to consider more durable options.

The Consequences of Past Trades: Missed Opportunities

The Yankees traded away one of their top pitching prospects for Montas and bullpen arm Lou Trivino—who also missed the 2023 season. Another trade saw starting third baseman Ezekiel Duran being sent to the Texas Rangers in exchange for Joey Gallo. Gallo had an underwhelming .159 batting average and .282 OBP over 82 games with the Yankees last season before being traded to the Dodgers. Meanwhile, Duran is flourishing in Texas, presenting yet another “what could have been” for the Yankees.

Josh Donaldson: A $50 Million Mistake

Adding insult to injury, the Yankees also took on $50 million of Josh Donaldson’s contract. At 37, Donaldson is past his prime and has contributed little to the Yankees, who have been winning more frequently since his departure.

Yankees’ Front Office Tensions: Steinbrenner vs. Cashman

Steinbrenner’s decision to intervene at the trade deadline casts a long shadow over Brian Cashman’s future moves. Although it’s widely believed that Cashman will keep his job, Steinbrenner might either take a more hands-on role or bring in trusted advisors, thereby reducing Cashman’s latitude for making unilateral decisions.

Looking Ahead to 2024: A Balancing Act

The likeliest path for the Yankees involves making smaller but significant moves while relying on the growth of their prospects in 2024. They may focus on development for the 2025 season, eyeing potential big-market acquisitions like Juan Soto. However, with Aaron Judge not getting any younger, the Yankees might still feel the pressure to act more urgently.

In this high-stakes environment, the Yankees’ strategy in the upcoming season could well be a defining moment for the franchise’s future.

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