“Complicated” has been a common word used to describe the legacy of former Orioles owner Peter Angelos since his passing in March. His impact as a philanthropist and champion for the Baltimore community was massive. His time as the owner of the team, however, was marred by controversy and losing seasons.

Since PressBox is a sports publication, the focus of our coverage of Angelos’ legacy is his time leading the Orioles. With his family also moving on from ownership of the team, we reflect back on “The 15 Moments of the Peter Angelos Era.”

1. Initial Spending

After buying the team in 1993, the Baltimore native swiftly improved the roster ahead of the 1994 season, boosting the excitement of fans. Rafael Palmeiro inked a five-year, $30 million deal just two months after Angelos assumed control. Future Hall of Famer Lee Smith, who won the ‘94 Rolaids Relief Man Award given to the league’s top bullpen arm, and veterans Chris Sabo and Sid Fernandez were also part of the initial spending spree. Aggressive efforts via free agency and trades continued the next five years, netting the team stars like Roberto Alomar, Mike Bordick, Kevin Brown, Eric Davis, Randy Myers, B.J. Surhoff and David Wells.

2. Refusal To Play Replacement Players

Angelos was perhaps never as popular in Baltimore as he was in early 1995. With MLB mired in a players’ strike, owners were prepared to attempt to put the squeeze on players by fielding replacement players. The Orioles’ owner chose to quite publicly take on his fellow owners by refusing to field scabs. The decision was a reflection of his pro-labor stance and also his desire to protect Cal Ripken Jr.’s consecutive games played streak, which would have been artificially snapped.

3. 2,131

Few moments in Orioles (and frankly baseball) history are as memorable as the night Ripken broke Lou Gehrig’s consecutive games played record. The buildup to the moment and the pageantry surrounding the record-tying and record-breaking nights were truly pitch perfect and stand among the most remarkable we’ve ever seen. But the postgame scene after the record fell was also a bit odd, as Angelos’ lengthy speech elicited boos while fans at Camden Yards waited to hear from the star of the moment himself.

4. Playoff Appearances In 1996 And 1997

Fans of a certain age might struggle with the idea that at one point, Peter Angelos appeared truly hell-bent on delivering a World Series title to Baltimore. Those free-agent acquisitions proved fruitful, helping the Orioles make back-to-back postseason trips. Both resulted in playoff series wins but ALCS heartbreak. (We don’t talk about what happened in ‘96.)

5. Jon Miller’s Departure

The relationship between Angelos and Orioles fans started to veer toward irreparable in this moment. The status between the team and its very popular play-by-play voice became very confusing after the 1996 season, with the owner acknowledging he’d prefer Miller adopt a style that would see him “bleed a little orange and black.” Miller departed for San Francisco, where his Hall of Fame career continues today.

6. Davey Johnson’s “Resignation”

The surreal nature of this exit is still difficult to grasp. On the same day that Davey Johnson received the AL Manager of the Year award (Nov. 5, 1997), Angelos accepted his resignation as manager. Johnson’s departure was not surprising. His relationship with Angelos deteriorated thanks in part to his insistence that Alomar pay a fine to a charity with which Johnson’s wife was heavily involved. Still, the Orioles had made back-to-back playoff appearances with their former second baseman at the helm, and the fan base was less than thrilled with his departure.

7. Albert Belle’s Contract

After a disappointing 1998 season and the departures of stars like Alomar and Palmeiro, the Orioles attempted to retool for the 1999 campaign. They signed veterans like Will Clark and Heathcliff Slocumb, but the centerpiece of the offseason was a five-year, $65 million contract they gave to slugger Albert Belle, making him the highest-paid player in the game. Belle was productive during his two seasons (a combined 60 home runs and 220 RBIs), but the teams were forgettable and a degenerative hip injury forced Belle into retirement. The deal is widely believed to have impacted Angelos’ willingness to pay top dollar for free agents in the following years.

8. Cuba Trip

While some decisions and moments during Angelos’ tenure were viewed as controversial, only one created a truly international incident. Angelos lobbied in the early years of his ownership for an opportunity to play a game in Cuba despite the trade embargo between the two countries. An ease on restrictions by President Bill Clinton in early 1999 paved the way for an agreement that allowed for an exhibition “home-and-home” series between the O’s and the Cuban national team. The trip to Havana occurred despite objections from the state department. The teams split the two games.

9. The Dark Years

The 1998-2011 stretch is what is typically most associated with Peter Angelos’ era as Orioles owner. It was … bleak. The Orioles finished in fourth or fifth in the AL East in all but one of those seasons (2004, when they finished third) and didn’t have a single winning season during that time. There were particularly notable indignities during the period, including a 4-32 stretch in late 2003 and a 30-3 loss to the Rangers in 2007.

10. Expos Move To D.C. And The Creation Of MASN

Understandably, Angelos was not interested in seeing the Montreal Expos move to Washington. The Orioles drew quite well from the D.C. market and he had no desire for a new team to cut into that. An agreement was finally reached to allow baseball to return to D.C., paving the way for the move to become official in 2005 and giving the Orioles the majority of the Nationals’ television profits. The move continued to be an issue, leading to a rare lawsuit between MLB teams and still ongoing battles about the TV rights nearly 20 years later.

11. Hiring Of Andy MacPhail

It was difficult to ascertain what the hiring of former Twins general manager Andy MacPhail might mean when he arrived in the middle of the 2007 season. But MacPhail ultimately proved to lay the foundation for the team’s success thanks to some shrewd moves, like trading Erik Bedard to Seattle for a package headlined by Adam Jones and drafting Manny Machado.

12. Hiring Of Buck Showalter And Dan Duquette

Another shrewd move made by MacPhail was the hiring of Buck Showalter as manager in 2010. The former Yankees skipper was initially seen as an uninspired retread by most fans. The same could be said of MacPhail’s replacement, Duquette. Both moves worked out quite well for Angelos and the Orioles, however.

13. Playoff Appearances In 2012, 2014 And 2016

Angelos was much less of a public presence in the 2010s as the Orioles returned to prominence. The club was the winningest in the AL from 2012-2016, but its three playoff appearances netted only one more ALCS appearance (2014) and more heartbreak.

14. Chris Davis Contract

What’s interesting about the final significant moment in Angelos’ ownership tenure is that it bucked the trend and gave Orioles fans what they wanted: a financial commitment to a player in the name of trying to win a World Series. But the seven-year, $161 million pact inked before the 2016 season proved to be one of the biggest albatrosses in the history of the game. It has been widely reported that Duquette and his staff did not want to do the deal with Davis but instead Angelos made the arrangement personally with agent Scott Boras.

15. The Late Years

Unfortunately, the final years of Angelos’ ownership and life were mired by family strife that played out publicly, including a lawsuit regarding the handling of Peter’s estate. There was confusion for some time about who was actually running the club until Peter’s son John was finally appointed. The family decided to sell a control stake in the club just months before Peter’s death.

Photo Credit: Jim Burger/PressBox

Issue 286: April/May 2024

Glenn Clark

See all posts by Glenn Clark. Follow Glenn Clark on Twitter at @glennclarkradio