Better yet, Angelos seemed determined to spend as much as necessary to restore the Orioles to glory. The club made the postseason in 1996 and 1997. More than 3 million fans annually packed Camden Yards. On the surface, everything seemed grand.
But the cracks had already begun spreading. Angelos failed to renew the contract of popular radio broadcaster Jon Miller. Manager Davey Johnson abruptly resigned after the 1997 playoff run in a contract dispute with Angelos. General Manager Pat Gillick quietly walked away the following season, tired of butting heads with ownership.
In 1998, the Orioles fell into futility. Gillick's successor, Frank Wren, left after only one season and said the Orioles would never win with Angelos in charge. It was a view that spread over time, with Sports Illustrated eventually naming Angelos the worst owner in baseball.
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Even when he didn't famously veto trades — to be fair, some of those moves ultimately worked out in the Orioles' favor — his natural instinct as an attorney to study all angles occasionally created an organizational paralysis until potential deals fell off the table. Meanwhile, the Orioles kept losing, and his reputation as a meddler was cemented.
"I don't know of any business where the owner can be called a meddler. That says a lot about people's mentality of what actually goes on," Anderson said. "What is he supposed to do? Just sit up in his office while people spend his money? Is that how it works? Pretty much [making final decisions], that's what owners do."
It hardly mattered when Angelos leveraged the arrival of the Washington Nationals into controlling interest in a new regional sports network. Fans remained skeptical he'd spend revenues from the Mid-Atlantic Sports Network to build a winner.
"Loyal ... to a fault"
In recent years, his story has taken another turn. When Angelos hired Andy MacPhail to run his baseball operations in 2007, he seemingly embraced a new direction. With the team finally winning again last season, he also received widespread credit for commissioning six sculptures at Camden Yards to honor Orioles greats.
Even at his most laudable moments, however, the Orioles owner has been reluctant to embrace the public. During the statue unveilings last summer, the youngest of Angelos' two sons, Louis, acted as family spokesman. And, with the exception of scattered boos, Louis Angelos' well-crafted speeches seemed to resonate with the crowds.
Louis, who in the past has spent most of his energies with the family's law firm, is emerging as the face of ownership in the past year. (He couldn't be reached for comment for this story.) His older brother, John, is still the club's executive vice president and is featured in the team's media guide; Louis is not. But John has taken a less public role recently after overseeing the creation of MASN and the spring training relocation to Sarasota in previous years.
Although rumors occasionally surface that the Orioles could be for sale, there never seems to be anything concrete to those whispers. There's also been no formal word as to who will succeed Peter Angelos as managing partner in the future.
The elder Angelos continues to work six days a week at his Charles Street law firm, often staying there until game time before heading to Camden Yards for the first pitch.
There's little evidence that Angelos has softened as a negotiator. He remains locked in a long standoff with the Nationals over the division of MASN profits, a source of great frustration for Washington baseball fans.
Longtime Baltimore sports agent Ron Shapiro has observed Angelos from many angles. He began as an enthusiastic supporter, but the relationship went frosty when Angelos let Miller, a Shapiro client, leave for San Francisco.
After 20 years, Shapiro gives Angelos significant credit for solidifying local ownership of the team, keeping Camden Yards vital, creating a major revenue source in MASN and helping facilitate labor peace in the sport.
"Though there are those who will lean toward some negatives of his legacy, there are significant accomplishments to support a positive legacy," Shapiro said.
Shapiro also praised Angelos for putting his trust in current executive vice president Dan Duquette and manager Buck Showalter.
"The recent success testifies to the impact of these moves," he said. "Now, all that he needs is a championship to put an exclamation point on the positive legacy."
In his previous three managerial jobs, Showalter worked for the Yankees' George Steinbrenner, the Arizona Diamondbacks' Jerry Colangelo and the Texas Rangers' Tom Hicks, a trifecta of ownership machismo and bluster. Showalter wasn't concerned when he took the job to work for Angelos.
"When you've been through certain things … you realize the difference between perception and reality," Showalter said. "Peter has been solid with me. Everything he has said has come to pass. We have a lot of open and frank discussions. I like blunt. He likes blunt. And he and his family have been classy to me and mine."
Showalter said when he joined the organization he received invaluable advice from late club executive Mike Flanagan: Keep the communication lines open with Angelos. Go talk to him, get to know him on a personal basis.
Once that relationship and respect are forged, Angelos exhibits deep loyalty that lasts for years, maybe a lifetime, his supporters say.
"One of the things that stands out is how loyal he is to some of us. Maybe to a fault. Including to myself. A lot of people would say including me," laughed Roberts, who has been plagued by injuries after signing a four-year $40 million extension. "That really to me is something that I think he stands for. And I think it is something we can all learn from."
Whether Angelos' legacy as club owner can come full circle if the Orioles continue to win on the field and, ultimately, capture a World Series title remains to be seen. But those who know the family believe nothing would make Angelos happier.
"Last year, he was so proud of being in the playoffs," Showalter said. "And I joked with him. I said, 'Don't get satisfied.' And he ain't. He knows we have a lot of years to make up for."