Taking charge of the Orioles, John Angelos emerges from his father’s shadow into a harsh spotlight

Back before he was in charge, John Angelos wrote lengthy missives complaining to “ownership” about being underpaid, underappreciated and surrounded by “rank incompetence” and “insane business practices.” He would offer ideas and analysis to “the supreme authority,” Angelos wrote on Feb. 3, 2010, only to be “met with dismissal or combativeness and personal attacks on my shortcomings and alleged ulterior motives.”

He wrote again six days later, according to a lawsuit that excerpted the messages, concluding, “it is clear to me that I am not best served by remaining in a day-to-day management role.”

John Angelos is far from the only disgruntled employee ever to vent to management, but in his case, the “ownership” and “supreme authority” he was railing against was not just a boss but his father, Peter Angelos.

Today, John Angelos holds the same chairman and CEO title once held by his father, the 94-year-old Orioles owner and legal titan who has been incapacitated by illness for the past five years. Perhaps John is now discovering just how heavy lies the crown that he once chafed under.

Amid a magical season for the division-winning Orioles, a talented, joyful team that has captured Baltimore’s long-suffering heart, Angelos has drawn fire as he emerges from his father’s long shadow.

The influence Peter Angelos wielded in Baltimore is perhaps matched only by his devotion to it, leading an investors group to buy the team in 1993 for a then-record $173 million to restore it to local ownership. But that often gets overshadowed by how he micromanaged the team during 14 straight losing seasons.

That’s something his 56-year-old son has pointedly avoided, giving Mike Elias, who was hired as general manager in 2018, free rein to rebuild the team, the fruits of which are as clear as the Orioles’ 101-61 record.

And yet, when John Angelos should be riding this cresting wave, he’s instead shown a propensity for getting in his own way: There was the unprompted and unkept promise to open the team’s financial books. The suspension of a broadcaster for referring accurately to the O’s previous losses. The ill-timed warning that the ballclub wouldn’t be able to sign its young stars long term without raising prices “dramatically.”

Even last week, on the night the O’s clinched the highly competitive American League East division, he jumped onto the scoreboard midgame to announce a deal to keep the team at Camden Yards for 30 years, which turned out to be more aspirational than legally binding. And certainly not a lease that would unlock $600 million in public bond money for improvements for the state-built and -owned Oriole Park at Camden Yards.

Yet for all the angst he generated this year, the team’s remarkable turnaround, likely baseball’s best story this season, has perhaps saved Angelos from even harsher criticism. The deeper the team gets into the postseason, the more is forgiven and even forgotten.

And should the team make it to the World Series? That could propel John Angelos to an unfamiliar place — out from under the eclipse of a father, who for all his self-made wealth and success, never managed to get the Orioles to that elusive mountaintop.

In the spotlight

On Saturday, as the team opened the AL Division Series in a city awash in orange, the spotlight was shining ever brighter on John Angelos.

While his profile has grown along with the team’s rise and his father’s exit from public view, few know much about the man who now heads the Orioles, the local institution that commands so large a share of the state’s emotional energy and its public funds.

Part of that is his own reticence. Despite frequently describing himself as “transparent,” he tends to refuse media interviews, and can be guarded in speech, often pausing to compose his thoughts. But behind the scenes, and in extended texts that he dictates by the screenful, a surprising amount of anger and aggrievement can emerge, say those who have been on the receiving end.

Taking on his father’s mantle was never going to be easy, given Peter Angelos’ singular drive, demanding personality and reluctance to share power. At his law firm, he was the sole partner and the other attorneys his employees; at the Warehouse — the O’s offices at Camden Yards — his was the final word.

“I do think that John believes he has something to prove,” former Maryland Stadium Authority Chairman Thomas Kelso said.

Kelso negotiated extensively with Angelos on a stadium lease until Gov. Wes Moore took office in January, and decided against reappointing him.

“I like John personally. He’s very smart and he has lots of creative ideas,” Kelso said. “It’s just that I don’t think he’s prepared by life experience and training to be the frontman and a spokesperson.”

Angelos declined numerous requests over the past several months to be interviewed for this article, and did not respond to specific questions sent via texts and emails.

His leadership role is perhaps one he was never meant to have, or was trained for by his father.

“Peter didn’t delegate well,” said Kenneth Feinberg, a lawyer and mediator who oversaw the 9/11 victims fund and a close friend of the Angelos family. “I told Peter for a number of years you have to know how to pass the baton to the sons. You have to have the transition plan in place.

“He didn’t provide a clear blueprint.”

Instead, when Peter Angelos could no longer handle his many-tentacled business interests, his family ended up in a bruising legal battle. Louis Angelos, 54, an attorney who has been managing his father’s law firm, sued his older brother and mother Georgia in June 2022, saying John made a power grab for the team and other assets, rather than abiding by their ailing father’s desire that they work jointly to manage them. Georgia, 81, countersued Lou, but the cases were settled in February under terms that remain secret.

It was Baltimore’s own “Succession” drama, the offspring at war, struggling to prove worthy of the inheritance. Like the HBO show’s aging magnate Logan Roy, Peter Angelos built his own fortune, starting a firm shortly after graduating from night law school in 1961 that ultimately won billions of dollars on behalf of those harmed by asbestos and tobacco. Like Kendall Roy, John Angelos’ prominence derives from being his father’s son, inheriting a platform he would not have otherwise.

Although Peter’s wife has claimed he never intended for the family to remain in the baseball business, John promotes big ideas for the Orioles and the city and believes he can guide the team effectively and avoid the upheaval of an ownership change. He has sought to broaden his influence well beyond baseball and, like a public official, often talks of helping redevelop the city’s downtown and uplifting Baltimore’s youth through social programs.

“Like his father, John has a deep and abiding commitment to the Orioles and the city,” said Alan Rifkin, an adjunct sports law professor and former Orioles attorney.

The tensions with his father, according to Louis Angelos’ suit, stemmed from John’s failure to pass the bar and join the legal profession that Peter considered his highest calling.

The family dynamic led to what one former team employee described as “constant power struggles” between the two, with John assigning something, only for Peter to overrule him.

Things came to a head in 2009, the suit said, when John stormed out of a meeting and the club’s day-to-day operations over his father’s refusal to consider spring training sites in Arizona, which Peter thought was too inaccessible for the fan base.

But by 2017, his health failing, according to the suit, the elder Angelos asked his prodigal son to return to the ballclub.

‘Will to win’

For all their differences, there are those who see a through line from Peter to John.

Peter grew up in Highlandtown, the son of a Greek immigrant tavern owner, attended the public Patterson Park High School and learned to box in the old Baltimore Athletic Association.

John grew up in Roland Park, the son of a successful attorney, and attended the private Gilman prep school where he won state titles in wrestling.

Their shared combativeness came to define them into adulthood.

When John Angelos derailed a January event with Baltimore Mayor Brandon Scott to argue with a reporter who asked about his family’s legal battle, it came as no surprise to at least one former wrestling teammate, who remembered him as intensely driven, “a super hardnose, tough-ass Greek kid.”

“His competitiveness and will to win stood out,” said another former Gilman wrestler, Henry Franklin.

The event, meant to herald the Orioles’ $5 million donation to the CollegeBound Foundation, turned into something of a harangue with Angelos telling the reporter it would be inappropriate to ask about team finances on Martin Luther King Jr. Day and to “get some perspective on life.”

In the end, he might have defeated himself, promising to open the team’s finances to the news media “next week,” something that not only he hasn’t fulfilled, but that continually gets thrown back at him.

Former teammates remember bonding with him over the agony of making weight for matches — he competed at 107 and 115 pounds — and say he had friendships beyond the team.

Classmate Steve Ciccarone described him as “a generous guy, a feisty athlete and very fun to be with.” He recalled the friends celebrating graduation by piling into a car for a raucous weekend at a farm on the Eastern Shore, and sharing “an awesome meal” at Shane’s, the fancy Haussner-esque restaurant in Timonium that Peter Angelos owned at the time.

John Angelos went on to Duke University, where a freshman directory showed him to be interested in politics and softball, and he graduated in 1989. He received a law degree from the University of Baltimore Law School.

Despite his status as the owner’s son and a team official, he was not “one of these blue-blood Baltimore people who didn’t interact with people outside their bubble,” said Cristen Pascucci, a friend of more than 20 years.

Pascucci, who previously worked in public affairs and now is a Kentucky-based activist for women’s maternity rights, said she and Angelos met through their overlapping social circles. While they didn’t date, she said they bonded over a shared love of classic and independent movies and the diversity of Baltimore’s neighborhoods.

But he also always has been exceedingly private, Pascucci said, and indeed, other friends did not return calls seeking comment.

In fact, Pascucci said, he is so protective of his private life, she didn’t learn he had gotten married until afterward.

Angelos is married to Margaret Valentine, who had been a singer-songwriter. While he often describes himself as a lifelong Baltimore resident, he and Margaret owned a couple of homes in her native Saratoga Springs, New York, before moving to the Nashville, Tennessee, area as her musical focus shifted from performance to management. When in Baltimore, they live in a harborside condo.

A longtime music fan, John Angelos has added musical programming to Camden Yards, a turnaround from his father, who questioned whether concerts made economic sense and didn’t want to let the ballpark “become some kind of honky tonk for various and sundry rock ‘n’ roll bands.”

In February at spring training, music was the first thing that came to mind when he described how his duties directed him away from the field.

”First, I have to do the concerts,” Angelos said. “Then, we have to do the PPP,” referring to the public-private partnership with the state, including the lease on Oriole Park. “And we’ve got to perform as these guys are performing on the field, meaning Brandon [Hyde, the Orioles’ manager] and Mike [Elias] and the team and the players.”

Palace intrigue

Shortly after the purchase of the Orioles, Peter Angelos brought both sons into the front office. Unsurprisingly, some of the baseball pros bristled over the perceived nepotism and that “the boys,” as they were known, seemingly had more influence with “the old man” than they did.

It was a tumultuous time both within the Warehouse and beyond. There was much palace intrigue, and a string of managers and executives passed through a seemingly revolving door.

Baseball players went on strike in 1994, and Peter Angelos, ever the champion of union workers whether they toiled in steel mills, shipyards or the baseball diamond, refused to go along with MLB’s plan to use replacement players.

Long-term, it was unclear what he envisioned for the team, or his family’s role in it.

Marty Conway, a former MLB and Orioles marketing executive whose tenure in Baltimore preceded the 1993 purchase of the team, said it was commonly known “within the baseball community” that Peter never intended for his sons to succeed him.

In her lawsuit, Georgia Angelos claimed her husband thought the team should be sold after his death, although he left the decision up to her. But John has asserted himself as the team’s leader at least for now, and in 2020, Major League Baseball team owners approved him as the Orioles’ “control person,” the executive responsible for the team.

Peter Angelos said early in his ownership of the team that he would rather his sons went on to do “more important” work as lawyers, as baseball was just “fun and games.”

Perhaps he had a change of heart in the intervening years, as both sons remained involved in various capacities, interviewing candidates for top jobs and handling myriad details involved in the complex organization.

For all the internal drama, there were high points for the team, from Cal Ripken Jr. breaking Lou Gehrig’s streak when he played his 2,131st consecutive game in 1995 to the O’s historic game in Cuba in 1999, the first American team to play in the country since Fidel Castro’s communist revolution.

By then, John Angelos, who had held the title of “chairman’s representative,” also had been named the team’s executive vice president, making him the number three in the organization.

Rick Schaeffer, Baltimore-based attorney who was instrumental in getting his friend Peter Angelos interested in playing in Cuba, said he sensed John’s “fealty” to his father.

“Basically, he really did just want to help his dad do something he wanted to do, something nobody else had done,” Schaeffer said of the Cuba trip.

In 2005, the Mid-Atlantic Sports Network, or MASN, was created in the wake of the Montreal Expos relocating to Washington as the Nationals and cutting into the Orioles’ historic market. John became CEO of the network, which broadcasts both teams’ games.

His work on the financial side of baseball has led him to bemoan, repeatedly and at great length, how difficult it is, relative to the NFL, for small-market teams like the Orioles to compete against larger, richer franchises.

These days, now firmly in charge, John Angelos reminds some of the mercurial father with whom he once tangled.

According to his brother’s lawsuit and those familiar with Peter Angelos’ businesses, he has let go several staff members and associates loyal to his father and sought to put his own stamp on operations — changing, for example, accountants and vendors.

They point to the August suspension of affable MASN broadcaster Kevin Brown, reportedly for citing team-provided statistics about the O’s previous struggles, which roiled the sports talk world for days without official comment from the team.

The incident drew comparisons to how the much admired play-by-play announcer Jon Miller was let go in 1996, with Peter Angelos saying he thought an O’s broadcaster should “bleed” for the team.

Then there was last week’s midgame announcement that the team and the State of Maryland had agreed to a deal keeping the Orioles at Camden Yards for at least 30 years.

The deal, widely misinterpreted as a new lease or extension of the one expiring Dec. 31, blindsided members of Orioles staff. The team had no official release prepared. A spokeswoman, contacted after the fact, said she only could “confirm the accuracy” of the announcement.

The next morning, the state and the team clarified the deal was a nonbinding memorandum of understanding, laying out possible terms.

Like father, like son

Much as his father was close to political figures, so too has John Angelos developed friendships with their successors. Scott, often in brightly colored team gear, is a frequent guest in the Camden Yards owner’s box, which offers an expansive view of the field below.

There, guests that have included politicians, lobbyists, public relations consultants and media members mingle in a setting that, except for the hot dogs, popcorn and baseball game playing out front, could be a reception in Annapolis or Washington.

Angelos, usually dressed casually, moves around the two-level suite, chatting with VIPs, and not generally engaging in fist-pumping or other displays of fan support.

Angelos has nurtured a friendship with the governor, who gushes about the Orioles and has referenced the Orioles’ winning ways in his political fundraising appeals. Moore and Angelos appeared together on the videoboard last week, celebrating what proved to be a step toward a new lease. Six innings later, the Orioles clinched the AL East, their third division title in the Angelos family’s three decades owning the team.

Emails, obtained by The Baltimore Sun under a public records request, show a warm relationship, with the two discussing the possibility of meeting up on Martha’s Vineyard over the summer, and the buzz surrounding the young team.

“Yesterday was extraordinary, and I am so excited to have you as not just a friend, but a partner in this work,” Moore wrote Angelos after throwing out the ceremonial first pitch of the home opener against the New York Yankees in April.

Moore featured Angelos in his 2020 book with former Sun reporter Erica L. Green, “Five Days: The Fiery Reckoning of an American City,” about the unrest following the police-custody death of Freddie Gray. Moore was among those taken with Angelos’ 21-tweet thread April 25, 2015, after growing protests downtown over Gray’s death caused traffic congestion around Camden Yards.

Angelos called it an “inconvenience at a ball game irrelevant in light of the needless suffering government is inflicting upon ordinary Americans,” and going on lengthily about how the unrest in Baltimore stemmed from the economic devastation brought on by a “political elite” that sent jobs abroad.

It was virtually unprecedented for a pro sports exec to speak out that way, but par for the Angelos family’s politically progressive course. Peter Angelos is a onetime Baltimore City Council member who subsequently ran unsuccessfully for council president and, on the city’s first racially integrated ticket, for mayor.

While he has not run for office, a poll of unknown provenance floated John Angelos’ name earlier this year as a candidate for U.S. Senate.

The friendship between Angelos and Moore will surely be tested in the coming months as they endeavor to turn the memorandum of understanding into a final lease before the current one expires Dec. 31.

Moore has been key in the lease negotiations, supporting Angelos’ vision of redeveloping the area around the ballpark into a live-work-play district akin to The Battery, the Atlanta Braves’ suburban home that the two visited earlier this year.

Angelos said in February that he hoped to deliver a new agreement as an “All-Star break gift,” but that time frame came and went much like his January promise to open the team books “next week.” A second self-imposed deadline to discuss the team’s financials “before spring training is over” similarly passed despite Angelos declaring, “When I say something … I’m gonna do it. I’m not gonna say it and walk away from it.”

Conway, the marketing executive, called these “unforced errors.”

“It’s kind of an undisciplined thing that I think, when you look at it, comes from not being in the spotlight on a regular basis and not understanding that your words have meaning beyond the venue that you’re in,” he said.

Angelos unnecessarily raised issues that fans otherwise would not worry about, Conway said.

“They don’t really care about the lease unless it’s not being signed,” he said. “They don’t really care about the profitability of the team unless there’s some question about it.”

Until a lease is signed, fans are left to fret over the team’s future.

In late summer of 2022, Kelso said he let John Angelos know the NFL’s Ravens were close to updating their lease. According to Kelso, Angelos — who has a penchant for arriving late for meetings and scheduled calls — said he would send over an Orioles term sheet in the next week. The document, a precursor to a lease, never arrived.

While it is rare for MLB teams to relocate, Louis Angelos’ suit suggested his brother’s consolidation of control could allow him to move the Orioles, perhaps to his adopted city of Nashville, which is among the cities hankering for a team.

That is something that neither John Angelos, nor the fans, the city, state or MLB say they want.

For now, the family appears to be in an unloading mode, with parts of Peter Angelos’ extensive real estate portfolio having been sold or on the market, and the law firm under conservatorship, which could lead to a sale. In this year’s team media guide, Louis Angelos’ name and photo, which used to run alongside that of his father and brother, didn’t appear on the partnership group’s page.

The family, meanwhile, retreated back behind the wall of privacy they assiduously maintained before the lawsuits aired their bitter quarrels.

Some close to the family shudder to think how the family patriarch would have reacted to all this, the sheer rage that erupted as the suits were being litigated, the lingering wounds between the once-close brothers.

“I’ve found over the years the most difficult disputes to resolve are those involving family,” said Feinberg, the mediator.

He added, though, that no one should underestimate Georgia Angelos’ ability to repair the damage.

“She’s formidable,” Feinberg said, “and she loves her sons.”

While comparisons are inevitable, John Angelos doesn’t say much publicly about his father, neither to acknowledge the shoulders he stands on, nor to highlight his different approach.

But, like his father, he doesn’t lack confidence or the belief that he should be in charge for a long time.

“I’m here for the long haul,” John Angelos said in February. “There is absolutely no plan to change the partnership group or to change the managing partnership structure that we have.

“I think we want to see this through.”

Baltimore Sun reporter Hayes Gardner contributed to this article.

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