The business of selling sports teams is a long, tedious process — moving at a glacial pace that fans can’t always appreciate.

At least, it normally is. The Orioles’ sale to David Rubenstein and his group is reportedly moving swiftly.

Major League Baseball Commissioner Rob Manfred told reporters on Thursday that the league would like to get the deal done “as soon as we can.” That involves a vetting process and reviewing reams of documents, but it’s possible that a deal unveiled Jan. 30 will be wrapped up in time for opening day March 28.

There are a few reasons Major League Baseball would like an owner like Rubenstein, who is extremely wealthy, has funded civic causes and rubs elbows with many others who own franchises. But the speed of the sale might also have to do with the league’s decadeslong grudges with the Angelos family, which at various times has been a stubborn voice of dissent and sometimes one of the MLB’s eyesores. It’s important to note, under the terms of the sale, the Angelos family will still be major investors in the team, but Rubenstein will make all the franchise’s major decisions as the control person.

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For those who need to brush up, here’s a history of MLB’s issues with the Angelos family during their three decades of stewardship in Baltimore:

Siding against owners during the 1994 strike

Arguably, Peter Angelos’ biggest stand against other owners was a courageous display of rectitude. Players went on strike in August 1994, leading to the eventual cancellation of the World Series. Before the 1995 season, Angelos was the only owner who refused to back teams with replacement players.

“There is no substitute for major league ballplayers,” Angelos told the New York Times in 1995. “Anyone who contends that is deceiving himself.”

While Angelos is now well known as one of Baltimore’s wealthiest citizens, he has blue-collar roots and frequently represented trade unions in his law career. It was not in his makeup to side against the players’ union. Although his decision was met with 92% approval locally, according to a poll Angelos commissioned, it rankled owners who were facing considerable financial losses from the work stoppage.

A factor in Angelos’ thinking was Cal Ripken Jr.’s impending eclipse of Lou Gehrig’s consecutive-games-played streak. If Angelos had agreed to field replacement players for games, The Streak would have come to an ignominious ending just months shy of the record. As fans warmed up to baseball again in 1995, Ripken’s 2,131st straight game is often credited with revitalizing the sport after the stoppage — the league probably owed Angelos thanks for that, though some owners refused to speak with him for some time afterward.

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Opposing the Expos’ relocation and creating MASN

If there’s something that stands out from Peter Angelos’ tenure, he was never afraid to be the odd man out. The other notable time when he was the lone dissenting voice came when the league voted to move the Montreal Expos to Washington, D.C., 29-1.

Angelos negotiated a lucrative deal by creating the Mid-Atlantic Sports Network and controlling the Washington Nationals’ broadcast rights in perpetuity, which has led to court tussles over just how much MASN has owed the Nationals. The Orioles controlling the Nationals’ broadcast rights has recently held up the sale of the team, as a potential new owner would likely want more clarity and control over MASN’s future (Rubenstein’s group is acquiring MASN as part of the deal, but any changes to the network or its rights are unclear).

Essentially, Peter Angelos finagled a rights deal unique to American sports that has become an MLB headache. It’s hard to fault Angelos for protecting his franchise and his family’s bottom line, but surely there’s no love lost with the league for being the odd man out 20 years ago.

The odor of losing seasons

Even the most ardent fan can admit that the game has changed drastically since the Orioles’ heyday, when they could hold on to homegrown talent for pennies on the dollar. But, as much as free agency and uber-rich rival franchises have hurt the Orioles’ competitiveness in the last few decades, the Angelos family has had a hand in it as well.

Since 1993 when Peter Angelos acquired the team, the Orioles have had 20 losing seasons while making the playoffs only six times. The worst of these stretches was from 1998 to 2011, when Baltimore never reached the playoffs. Success at the beginning of the Angelos era quickly petered out, with lost seasons at the end of Ripken’s career, along with more than a decade of diminishing returns amid widespread reports of Angelos’ meddling with the team.

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The Orioles’ worst seasons of late were a product of a tanking strategy, and frankly if you look at the team and the farm system now under Mike Elias, it worked. But rosters that lose by design are still generally odious to the leagues, who don’t enjoy rupturing the illusion that every team has the same opportunity to succeed.

Bottom line: The Orioles have not been to the World Series since 1983 and have seen a lot more meaningless seasons than meaningful ones in the interim. Until recently, it felt like Angelos’ stewardship was not marching the franchise toward its championship goals.

Lease labor pains

(l) Orioles CEO John Angelos and (r) Maryland Gov. Wes Moore
Orioles CEO John Angelos (left) and Maryland Gov. Wes Moore. (Ulysses Muñoz/Getty Images, The Baltimore Banner)

Although Camden Yards is under contract for the foreseeable future, it took a lot of heartache to get there — heartache that probably wasn’t necessary for a few reasons.

The $600 million in state bonds made for as competitive a package as any market of Baltimore’s size is putting forward to fund baseball stadium projects. But John Angelos sought more, specifically development deals that dragged out the process for the better part of a year. Even with a great relationship with Gov. Wes Moore, Angelos didn’t make much progress on the development front (discussions were kicked down the road in the new lease) and didn’t attend the lease signing in person.

There has been plenty of academic work to suggest public funding of sports teams and their stadiums is not a good investment, and leagues are image-conscious of their owners turning their noses up at substantial subsidies. Although Angelos said he was never going to relocate the team, the implication that the state bond money — which the Ravens quickly accepted and applied to their own stadium upgrades — wasn’t enough for him to get a deal done seems unflattering for MLB’s optics.

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Unnecessary commentator drama

Kevin Tehansky holds a sign in support of broadcaster Kevin Brown at Oriole Park at Camden Yards during a game in August. (Julio Cortez/AP)

From the start, the suspension of play-by-play announcer Kevin Brown seemed petty and avoidable, making it all the more remarkable just how much negative attention it brought the franchise. When it came out that Brown had been taken off MASN broadcasts for reciting a basic fact perceived as critical of the team, it drew widespread condemnation on broadcasts throughout MLB and in news and sports in general.

It’s not the first time the Orioles have sparked strange controversies with the voice of the team. Jon Miller was run out by Peter Angelos, reportedly because he wanted someone who would “bleed orange and black” (and Miller did, for the San Francisco Giants for much of his Hall of Fame career). The Orioles made a controversial decision not to bring back popular play-by-play man Gary Thorne after the 2020 season.

Especially when teams are hot, fans tend to associate highlights with the voices describing the action — and at the moment he was taken off the air Brown was, for many fans, the voice of the rebuild and synonymous with the team’s most exciting season in years. The weirdness of allowing a petty qualm about a team statistic blunt the enthusiasm around the franchise was an unforced error by ownership and a reminder of how much meddling has gone on in the broadcast booth over the last few decades.

Kyle joined The Baltimore Banner in 2023 as a sports columnist. He previously covered the L.A. Lakers for The Orange County Register and myriad sports at The Salt Lake Tribune. He’s a Mt. Hebron High and University of Maryland alum.

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