With big decisions looming for Orioles, John and Louis Angelos assume larger roles in organization

During a five-year renaissance in which the Orioles won more regular-season games than any other American League team, criticism of the team’s ownership and speculation about the future of the franchise cooled considerably.

Few doubted that managing partner Peter Angelos still had the last word on major organizational decisions during that happy segment of the Buck Showalter-Dan Duquette era, but the front office was making enough of the right calls to temper the negative narrative that developed during the 14 straight losing seasons leading up to it.

That was then, of course. Now, the Orioles are in the middle of an awful start, the 88-year-old owner is battling health problems and it’s fair to wonder who’s running the show.

The long answer is a bit complicated, but the short one is that while Peter Angelos remains the boss, his two sons have taken on increasing ownership responsibilities over the past decade and now are involved in just about every aspect of the organization.

That much has been confirmed by Brady Anderson, the team’s vice president of baseball operations, who has emerged as a trusted adviser and friend to both John and Louis Angelos. Peter Angelos and his sons did not comment.

Club officials have long been tight-lipped about the ownership chain of command, and the lack of a clear hierarchy below Peter Angelos has contributed to some confusion within the organization.

It doesn’t help that the Orioles collapsed late last season and finished with their first losing record since Duquette arrived in 2012. Things worsened dramatically this season, with the Orioles’ start their ugliest since they opened the disastrous 1988 season with 21 straight losses.

While there is no overt evidence of a power struggle in the Warehouse, where the O’s offices are, uncertainty is everywhere. The owner’s advanced age raises questions about a succession plan, with John the widely presumed heir. Showalter and Duquette are in the final year of their contracts. Superstar Manny Machado, de facto team captain Adam Jones, record-setting closer Zach Britton and All-Star setup man Brad Brach are all eligible for free agency after this season.

There are a lot of decisions to be made between now and the end of the next offseason — when or whether to deal Machado among them — and it’s unclear to a lot of people outside the management inner circle, and even inside it, according to sources, who exactly will be making them.

John and Louis have long had roles in the organization, with Anderson saying he first noticed them assuming increased ownership-related responsibilities around the time Andy MacPhail became president of baseball operations in 2007.

But in recent months, John has taken more control of the business aspects of the team with Louis overseeing the baseball operations, according to sources. Louis played a key role alongside Anderson in negotiating the deals for free-agent pitchers Alex Cobb, Andrew Cashner and Chris Tillman this past spring training.

John, 50, a lawyer who graduated from Duke University and the University of Baltimore School of Law, is the team’s executive vice president and has been the Mid-Atlantic Sports Network’s president and chief operating officer since the infancy of the team’s television network.

Louis, 48, a Johns Hopkins University and St. Thomas University School of Law graduate, is a member of his father’s law firm and an Orioles ownership representative.

It has been speculated — and was even articulated by Peter Angelos during the early years of his ownership — that John would someday take the reins of the ballclub and Louis would oversee the huge law firm, but Anderson said recently that the brothers’ roles are evolving differently.

Anderson said Louis has been more involved on the legal side and John has been more involved on the television side.

"But it’s inaccurate to say they haven’t been collaborating on all three entities [MASN, the team and the law firm] all the time for 25 years, because they have,” Anderson said.

Anderson views the relationship between John and Louis as a partnership, with both having fairly equal input in the baseball team’s operation.

“Lou was intimately involved in the interview process for the GM, the hiring of Dan,” Anderson said. “As far as I know, he was one of only three people who were in that process. And if I didn’t know Lou, I would think, ‘That guy, he’s been involved in baseball the whole time I’ve been here.' He’s been doing both, and John’s title is president of MASN. There is all sorts of crossover, as there should be because of their capabilities.”

Several sources have confirmed that Peter Angelos has been limited by back, leg and other health problems the past several months, which has allowed — even required — both sons to play more visible ownership roles. And that is not just about appearances.

John has focused on outreach to the team’s fan base. While he has been the team’s executive vice president since 1999, more of his ideas have been implemented in recent years. He also has become more visible as a voice representing the Orioles in the team’s news releases.

The club’s “Kids Cheer Free” program, which allows every adult who purchases an upper-deck seat to get two free tickets for children ages 9 and under, was John’s brainchild. The team also recently announced a season-long schedule of theme nights, which includes several new events such as LGBT Pride Night, Yoga at the Yard and Bark at the Park Night.

John also has worked to build a strong relationship with Sarasota County, Fla., planting strong roots around the team’s spring training home with year-round philanthropic efforts throughout the community that include promoting a healthy lifestyle and the area’s arts scene.

John and Louis both were heavily involved in moving the club’s spring training home to Sarasota from Fort Lauderdale, Fla., in 2010. In the coming years, they’ll likely have to work together on a new lease at Camden Yards, since the original one is set to end after the 2021 season — although the team has the option to extend the lease for five more years.

Louis, meanwhile, has worked behind the scenes as an ownership representative. He was a key figure, for example, in putting together the Orioles’ historic exhibition trip to Cuba in 1999.

But beginning this past offseason, Louis took on a larger leadership role in baseball operations, assessing the allocation of resources throughout all departments, from the major league team to player development to the draft and international scouting. He is keeping tabs on how decisions are made, who is doing what and how to become more efficient in baseball operations, according to a source.

Along with Anderson, Louis played a key role in negotiating and executing the signings of the team’s three big free-agent acquisitions in March — Cobb, Cashner and Tillman — serving as a critical link to his father.

According to the three pitchers, the team made them feel wanted during a slow free-agent season, keeping in contact with them early and often. That contrasted with the reputation Duquette developed in the industry as someone who worked methodically and waited out the market. However, the more aggressive approach didn’t mean the deals came together more quickly than in the past. All three involved lengthy negotiations, and none of the three pitchers signed until after the start of spring training.

Anderson’s growing role in the front office has spawned speculation that he might replace Duquette as general manager, but he told The Baltimore Sun recently that he is not interested in becoming the team’s general manager because the requirements of that role might inhibit his ability to work directly with players. Since becoming a special assistant to Duquette in 2012 and then vice president of baseball operations in 2013, Anderson has had a unique multifaceted role that includes working one-on-one with players and overseeing the team’s strength program.

“I want responsibilities and I have a lot of responsibilities," Anderson said, “but a lot of things I do I might not be able to do if I were the GM. I have aspirations to do more and more and more. There’s no doubt. I’m not going to hide that and I never have. I certainly believe I’m capable of doing more. Look, if I’m doing what I want to do, if I’m doing things that are helping the team, I can help the GM keep his job and keep that sort of continuity."

There also has been speculation that Anderson might be elevated to club president in a role similar to the one played by MacPhail during the late 2000s. Anderson does not deny that such a possibility interests him.

“As far as president and more responsibilities, sure, I’m ready for them,” Anderson said. “But that doesn’t necessarily have anything to do with Dan’s current status. It really doesn’t. They’re not mutually exclusive — my desires and the current GM having to do something else.”

Whether Showalter and Duquette are part of the decision-making hierarchy beyond this season remains to be seen, but both expressed a desire as recently as this past spring training to return.

While there’s long been a perception of tension between them, their partnership since 2012 worked to bring the Orioles out of the darkness of 14 straight losing seasons. That’s despite the fact that Showalter has had more influence than typical field managers since he was hired in 2010, and that Duquette hasn’t had autonomy over baseball decisions.

Showalter is regarded as one of the best managers in the game, but lost some of his luster throughout the organization, including in the clubhouse, after the 2016 AL wild-card loss when he didn’t use Britton. Duquette also lost some favor with ownership when he flirted with becoming president of the Toronto Blue Jays after the 2014 season.

The Orioles’ poor start this season hasn’t helped either of them.

Duquette appeared to move more decisively this past winter when he openly shopped Machado at baseball’s winter meetings and received more than a half-dozen offers. The Orioles turned all of them down — even a few, according to a source, that were turned down by the ownership despite some in the baseball operations department believing they would have helped the team build for the future. Also, last summer, the Orioles had a deal in the works to move Britton to the Houston Astros, but ownership vetoed it as well.

With so much potential change facing the organization, an overhaul of the Orioles’ decision-making hierarchy seems inevitable, if impossible to predict.

By all accounts, Peter Angelos is still in charge and his sons have grown into important roles that are preparing them to take full control of the franchise some day.

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Baltimore Sun reporters Jeff Barker and Jon Meoli contributed to this article.

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