The echoes of the New York Yankees‘ dynasty under George Steinbrenner and Joe Torre are often measured in championships, but for one former star, their true legacy is measured in salvation.

Under the leadership of George Steinbrenner, the Yankees won seven World Series championships and 11 American League pennants.  The team built a reputation for housing some of the biggest names in the business and spending aggressively. The “Boss” was known for his dominant personality, as well as his one of the best scouting abilities in the league. A fact that the two-time Yankees World Series champion (1996 and 1999) recently confirmed.

“This Morning I Was Thinking About The Boss, George And Joe Torre. I want to express my deepest gratitude to The Boss, George Steinbrenner. And Joe Torre for giving me a real opportunity to play with the Yankees when so many others in baseball were calling me a loser because of my struggles with drug addiction. Their belief in me went beyond my past and saw the potential for who I could become,” Darryl Strawberry shared via Instagram.

Darryl Strawberry, the 3x overall World Series champ (another with the New York Mets in 1986), had one of his best times with the Yankees. In fact, he helped the team reach the 1998 World Series, too, hitting .247 with 24 homers across 101 games. Even though he could play in the Fall Classic because of colon cancer and surgery, his stats assisted the team with a 114-win season, and ultimately celebrate the ring for Darryl Strawberry, defeating the San Diego Padres.

Strawberry was proof of determination and Steinbrenner’s scouting ability.

Strawberry’s Yankees stint was defined by dominant on-field stats and turbulent off-field events.

Steinbrenner was the primary advocate for signing Strawberry in 1995, despite opposition from some of his own baseball executives, including GM Bob Watson. Steinbrenner stated he wanted to help Strawberry see that his life was not wasted.

“We are supportive of Darryl, and we shall do everything possible to help him meet the challenge ahead,” Steinbrenner noted back then.

After debuting with the Mets in 1983, Strawberry’s career began to unravel.

He entered rehab for the first time in 1990, the same year the Mets released him following a reported physical altercation with captain Keith Hernandez, capping a two-year stretch in which he played just 75 games.

The Dodgers signed him, but he was mostly sidelined with injuries and personal problems. LA released him in 1994 after he failed to show up for a game. The Giants also tried their hand with Strawberry, but nothing changed until the Yankees came on board in 1995.

Strawberry proved Steinbrenner right.

He batted .255 with 41 home runs in 231 games for the Yankees through 1999. His diving catch in the 1996 World Series Game 6 and his .333 batting average in the 1999 World Series were two of the Bombers’ historic moments.

Steinbrenner trusted the right talent, and so did the Yankees’ then-manager Joe Torre.

“They all start from scratch with me,” Torre noted.

Strawberry unleashed his second chance with the Yankees, adding three more rings to his collection. He also made sure to credit Torre.

That takes us back a little to 1948.

The team was the Oakland Oaks of the Pacific League Coast, and the player was Billy Martin. The major drawback for Martin was his temper.

Oaks trainer Red Adams persuaded the team’s new manager, Casey Stengel, to try the 2B out. And he did. Martin worked closely with the team to learn, grow, and earn his spot on the active roster. Eventually, he became a team leader, active in brawls on the field and a loud and annoying bench jockey in an era when a player often had to contend with a stream of insults from the opposing team’s dugout. The Oaks won the PCL pennant and the Governors’ Cup playoffs. All that happened while he kept dreaming of becoming a Yankee, which also became true in 1950.

But as Strawberry credited the Yankees’ then-front office, we wonder what would happen if their current front office acted the same.

The Yankees’ current front office has yet to play a risky game

While the Yankees under George Steinbrenner were known to go all out, aligning their winning mentality, the current roster is different. At least by how the Yankees are managing their prospects, Strawberry would surely not be very happy about it.

For instance, Jasson Dominguez is arguably the best example of botched player development by Brian Cashman and Aaron Boone.

He batted .257 with 10 home runs last year and hit three homers while maintaining a batting average above .300 in spring training. However, just as fans expected to see him on the 2026 Opening Day roster, the Yankees optioned him to the minors.

They decided to continue with Ryan McMahon despite his struggles in 2025. He batted .208 with the Yankees last year and is currently struggling with .140.

Boone and Cashman are still promoting him on the active roster, but not Dominguez.

The front office made a similar mistake with Oswald Peraza, trading him to the Los Angeles Angels last year over poor stats, only to watch him bat .267 with 4 HRs this season.

Now, Strawberry crediting George Steinbrenner and Joe Torre just offered a reality check for the current front office to take risks. The Bombers were never a franchise with safe bets.