Who's in charge of rebuilding the Orioles at the trade deadline?

GM Dan Duquette and manager Buck Showalter are the O's brain trust -- for now. AP Photo/Elise Amendola

THE ALL-STAR GAME hasn't even arrived, and the Baltimore Orioles are already 33½ games out of first place in the American League East. But that mind-bending reality can't convey the magnitude of the challenge at Camden Yards, where the outlook is so bleak, even a recent Halfway to Christmas promotion and a "Buck Snowalter" snow globe giveaway couldn't provide a reprieve.

The Orioles are 31-82 since the start of last September. They still owe more than $100 million to Chris Davis, a 32-year-old erstwhile slugger with a .489 OPS and a minus-2.3 WAR. The team's new free-agent pitching additions are 5-23 with a combined 6.14 ERA. And several familiar faces, from the star infielder and face-of-the-franchise outfielder to the manager and general manager, are in the waning months of their contracts.

The time has come for some hard decisions. As the Orioles try to spin Manny Machado, Adam Jones, Zach Britton and other impact veterans into long-term assets that could accelerate a rebuild and chart the course of the franchise into the 2020s, some crucial questions must be addressed:

  1. What changes will be made in the next few weeks?

  2. Who will be making them?

  3. Who will be around after the 2018 season to clean up the mess?

As the Orioles determine who stays and who goes before the July 31 non-waiver trade deadline, the intrigue is compounded by the unsettled status of general manager Dan Duquette and manager Buck Showalter. They join a clubhouse full of players who are trying to stay engaged while a team that began the season with hopes of wild-card contention, at the very least, watches the New York Yankees and Boston Red Sox ascend to a different stratosphere.

"It's hard not to think about, especially when you keep hearing, 'What are the Orioles going to do at the deadline?'" Britton said. "I know people are like, 'Just focus on baseball.' But you're human. You've got families and friends who are like, 'What's going on? Where are you going to be?' When you're winning, you're just focused on one thing. When you're losing and you have so many guys who could be free agents, from management to players, your mind drifts and wanders a bit into areas it shouldn't."

The Orioles are a textbook case of a competitive window slamming shut and sentiment taking a backseat to economic reality. The Pittsburgh Pirates faced a similar situation when they traded Andrew McCutchen and Gerrit Cole during the offseason. But at least GM Neal Huntington was around to handle the fallout and manager Clint Hurdle was in the dugout to try to meld the pieces into a cohesive unit. Regardless of how Pittsburgh fans feel about that leadership tandem, there's something to be said for stability and accountability in decision-making.

Duquette, the man entrusted with doing the outreach and fielding the offers, could be gone in four months. Showalter, who has been making out lineup cards at Camden Yards since 2010, could join him. Against that unsettled backdrop, vice president of baseball operations Brady Anderson is taking on various unspecified roles within the organization. Brothers John and Louis Angelos will be entrusted with making the big calls amid the declining health of their 89-year-old father, Peter, and ongoing litigation with the Washington Nationals over the MASN television rights fee dispute.

By any definition of "rebuild," that isn't an optimal scenario.

"Invariably, whoever gets the job might not like the package they got back for Manny," a National League personnel man said. "So right off the bat, you have this excuse for a new person to say, 'We traded a commodity and didn't get enough back, in my opinion.' That puts you behind the eight ball. And you also have to wonder: Are the sons going to run the team like their father did? For a lot of his reign, to be honest, it wasn't good. I think those are all valid questions."

AS THE ORIOLES navigate the challenge of balancing short-term action with long-range planning, where are they headed organizationally? Here's where things stand at the moment, according to multiple sources interviewed by ESPN.com:

• Barring a surprise or a change of heart, Showalter and Duquette appear safe for the rest of the season. John and Louis Angelos value the contributions the two men have made to the franchise, and they're determined not to act impulsively to satisfy the talk-radio masses. Things are ugly now, but sports fans in Baltimore will turn their attention to the Ravens soon enough. Anger will turn to apathy, if it hasn't already, and the brothers can take stock at the end of the season and chart a course amid calmer circumstances.

• Any and all options are on the table. That includes bringing back both Duquette and Showalter or cutting ties with both and starting from scratch. The Orioles have also discussed the possibility of bringing in a "consultant-type" person to assist Duquette and strengthen the front-office team.

• As Ken Rosenthal of the Athletic reported, the Orioles recently spoke with former Los Angeles Dodgers GM Ned Colletti. Multiple sources described the discussion as more a professional courtesy than an actual job interview. But it did provide a glimpse into where the Orioles might be going.

"As long as the Angelos name is attached to it, you know you're going to have to run the team not the way you want to run it but the way someone else thinks it should be run," a personnel man said. That's the general industry perception under the Angelos regime. So the Orioles could be looking at a field of former GMs who are either out of the game or working in different front-office positions and might be willing to accept a leadership role with less authority.

Colletti, Jim Hendry, Dan O'Dowd, Wayne Krivsky, Dan Evans and Larry Beinfest are among the former GMs who could fit the profile. It's worth noting that Duquette had been out of MLB since 2002 and had been running a baseball academy in Massachusetts for nine years when Peter Angelos hired him to run the Orioles in 2011.

• In his expanded role, Louis Angelos attends quarterly owners meetings and keeps an eye on industry trends and the operating models of other franchises. The Orioles have watched the dynamics in Minnesota, where the Twins have gone with a two-pronged decision-making tandem of Derek Falvey and Thad Levine, and in Philadelphia, where Andy MacPhail and a band of former Baltimore front-office execs have helped the Phillies return to contention with a focus on analytics.

Still, there's skepticism in the industry as to whether the Orioles would hire a rising, young executive with an analytics background and give him the power to make sweeping changes. "That seems out of their wheelhouse,'' one big-league executive said. The Orioles' relationship with the commissioner's office is also strained because of the MASN dispute, so it's unlikely the Angelos brothers will be picking up the phone and bouncing ideas off Rob Manfred anytime soon.

• The Orioles could carve out a more expanded role for farm director Brian Graham or make a play for Ned Rice, who left Baltimore to work with Matt Klentak in Philadelphia's front office in 2016 after 11 years in the Orioles organization.

• On the manager front, Jon Heyman of Fancred recently mentioned Rick Dempsey, Mike Bordick and Billy Ripken as potential options if Showalter goes. A source said the Orioles were merely spitballing those names and none has been approached or is under active consideration. Of the three, Bordick would be the most plausible candidate, if he decided he was interested.

Amid the flurry of speculation and what-ifs, both Showalter and Duquette have publicly stated that they would like to stay and try to turn things around.

"My heart is in Baltimore," Duquette said. "We've tried to put a competitive team on the field every day."

Showalter, similarly, told ESPN.com that he would be comfortable staying even if the Orioles decide to tear things down and resign themselves to playing kids and losing lots of games over the next few years. He knows the drill from his previous career stops with the Yankees, Rangers and Diamondbacks.

"I've done that my whole life," Showalter said. "That's fun, especially in-game -- as long as everybody is pulling on the same rope and has an understanding of what you're doing and how you're going to do it. I'm not saying it's easier or necessarily simpler, but it's not as much of a moving target.

"I love Baltimore. It's been great to me and my family, but I also have a lot of respect for the Angelos family, and it's their decision. I always take a job like it's my last job. I'm not coveting anything but to try and figure out a way to get us back on track. You don't do anything in survival mode. You have to do what is best for the long term."

In nine seasons with the Orioles, Showalter has worked to shed his reputation as a micromanager who eventually wears out his welcome with a team. But things have gotten progressively worse since his fateful decision to pitch Ubaldo Jimenez rather than Britton in the 2016 wild-card loss to Toronto, and now ownership has to decide if his message still resonates in the clubhouse. At various points in his tenure, Showalter has been mentioned as a potential GM candidate. But that speculation appears to have passed.

"I have a lot of respect for things I haven't done," Showalter said. "I'm not going to go try to land a plane. I haven't been a pilot, so I'm not going to go up in the cockpit and try to tell him how to do that. I'm not going to go into surgery and tell a doctor how to stitch something. I have a lot of respect for that job. I've been fortunate to be around a lot of good general managers, including Dan. I'm just focused on what we have to get done here, short term and long term, wherever life and the game take me.

"I understand we haven't been [good] the last two years. I understand how this works. But I love working with these guys, and I love being around them. Times like this are what separates you. I'm not going to quit talking to somebody, whether it's the media or whatever. There are no sides. If something is forcing you to pick a side, then you need to walk away from it. There are no sides. There never have been."

THE ANGELOS BROTHERS do not give interviews, and Anderson has tried to maintain a low profile, so the Orioles are not exactly adept at delivering a cohesive message. Inevitably, the silence from the top leaves the organization rife for industry rumor and long-standing perceptions. Two of the most prevalent: The Orioles' structure is a recipe for inertia as decisions move up the chain, and free-agent signings and trades are always harder for the O's to consummate because of the exacting nature of their "Navy SEAL" physicals.

"There are 30 ownership groups, and they all have their quirks," the GM for another MLB club said. "I think some things are overblown. But I do think there's something to be said for the ominous nature of their medical reviews. It's like, 'There's no way we're getting this guy to the Orioles.' If your guy sneezes, you're like, 'Oh my god, we can write them off.' That's the bigger complication."

Any discussion of the Orioles' decision-making process must take into account the disparate personalities involved and a hierarchy that is, at the very least, unorthodox.

The relationship between Showalter and Duquette has typically alternated between businesslike and frosty. One talent evaluator recalls how scouts would sit in the stands during batting practice, watch the two men stand side-by-side with arms folded and wonder who might say something first.

In a perfect world, Brady Anderson would be a perfect buffer. He is bright, well-read, engaging and inquisitive in a Gabe Kapler sort of way. Anderson has an interest in everything from analytics to nutrition to numerous other innovations to improve player performance, and he has maintained a workable rapport with both Showalter and Duquette.

"I've always had a constructive relationship with Brady," Duquette said. "He's passionate about the Orioles, and he's passionate about a couple of areas in particular where he does a good job."

The question is: Which areas? Anderson is a confidant of ownership, but he also has an office adjacent to the weight room and works out with the players. He's involved in player evaluations and contract negotiations, but he isn't in a position where he's publicly accountable for decisions or has to answer to the media for them.

The Orioles have a structure in place in which Duquette is entrusted with negotiating deals. But Anderson flew to Texas to negotiate with Andrew Cashner during the offseason, and he has been involved in discussions with Alex Cobb, Chris Tillman and other Orioles. Two sources cited examples of players or agents reaching out to Anderson when they thought Duquette was taking too tough a stance in contract talks. The blurred lines can reflect the lack of a unified front and pose a temptation for players and/or agents to try to do an "end around" and circumvent the process.

People close to the Orioles also cite Anderson's desire to get the absolute most out of players -- whether it's through one-on-one work with Chris Davis or a budding prospect on the farm. While Anderson's passion is admirable and his interest in player performance is heartfelt and real, he runs the risk of intruding on the coaches' territory.

"Brady lives and breathes it," one Orioles official said. "He wants to make every guy a cause. He'll see a kid in A-ball and say, 'I can make him better.' That's great from an organizational standpoint. He wants to work with the development people. He'll set up the tee and engage in a dialogue. But you're going to ruffle feathers because you're asking people to do things a little bit differently."

THE 2018 SEASON in Baltimore, while relentlessly depressing, obscures a recent stretch of winning unlike anything the city had seen in a while. After 14 straight years without a postseason appearance, the Orioles began a run of three playoff appearances in five seasons from 2012 to 2016. Duquette and Showalter took a team that hadn't reached October since the days of Rafael Palmeiro and Mike Mussina and led it to an average of 89 wins a year during that span.

But the model was unsustainable. The farm system, while improving, has consistently rated poorly in recent years, and the Orioles have had a hard time producing front-line pitching. Kevin Gausman and Dylan Bundy have performed more like middle- or back-end-of-the-rotation types than stars, and Hunter Harvey, another big prospect, has yet to fulfill his potential because of a series of injuries.

The organization's forays into free agency have not gone well. Ubaldo Jimenez's $50 million deal was a fiasco, and the Orioles hit a trifecta of despair this spring when they spent a combined $76 million in free agency for Cobb, Cashner and Tillman. Those moves added $22 million in 2018 salary obligations to a team that's playing .282 baseball.

Need reason to feel worse? Jake Arrieta blossomed into a Cy Young winner after leaving Baltimore. Zach Davies -- traded for Gerardo Parra -- won 17 games with Milwaukee last year, and Josh Hader -- traded for Bud Norris -- has blossomed into baseball's premier bullpen strikeout machine with the Brewers.

Sources say Duquette has grown increasingly frustrated with some of the limitations and organizational decisions that have hamstrung him in recent years. Peter Angelos drove the decisions to sign Chris Davis to a $161 million deal and re-sign Mark Trumbo to a $37.5 million extension in January 2017. The 2018 Orioles lack speed, they rank third in the American League in strikeouts, and they're last among MLB clubs with minus-81 defensive runs saved.

The O's operate with one of the smallest scouting and analytics contingents in the majors, and they've done next to nothing in the international realm. In 2011, Duquette brought in longtime international scouting guru Fred Ferreira, aka "the shark of the Caribbean," to mine Latin America for the Orioles. But the Angelos family was too skeptical of Ferreira and his scouts to invest any money in bonuses, and the team allowed Ferreira's contract to lapse over the winter. While Louis and John Angelos are committed to spending more money internationally, the process will take time, and the Orioles are clearly behind the curve.

As Duquette waits for Baltimore ownership to determine his status, it's with the knowledge that the Toronto Blue Jays wanted to hire him as their club president and CEO in 2015. But Peter Angelos refused to let Duquette out of his contract, and the Jays hired Cleveland's Mark Shapiro to fill the position.

"I don't think it's easy to be Dan with the Orioles," a person familiar with the Orioles' front-office dynamic said. "I don't think he has a lot of flexibility to do the things he wants to do, but that's partially his fault too. He's not a communicator. It's the general manager's job to make sure everybody internally is on the same page with what's going on, from ownership down to the people that work for you. That's not really Dan's strength."

THE ORIOLES HAVE a distinct pecking order of assets to sell between now and the July 31 non-waiver deadline. It's headed by Machado, a three-time All-Star whose next team will be just a pit stop to a massive, nine-figure deal. He's enough of a potential stretch run presence that the Dodgers, Cubs, Diamondbacks, Phillies and Indians are among the contenders jockeying for 2.5 months of his services.

Jones is a franchise favorite who is climbing the ranks of organizational greats. But he has the right to veto any trade because of his 10-and-5 service-time status, and his defensive metrics aren't helping his appeal to suitors. Jones has tallied minus-40 defensive runs saved over the past three years, according to Baseball Info Solutions, and he ranks 34th among MLB center fielders this year with minus-18 DRS. In light of Jones' contract leverage, moving him might be a challenge.

Baltimore's bullpen picture continues to evolve -- and not necessarily in a good way. Veteran Darren O'Day is off the market after season-ending hamstring surgery. Britton, who came perilously close to being traded to Houston at the 2017 deadline, has a 5.59 ERA in 10 appearances since his return from Achilles tendon surgery. Brad Brach is an attractive option, but he has a 1.67 WHIP and doesn't necessarily stand out in a market loaded with relief arms.

If the Orioles want to think bold, they could try to move Gausman or infielder Jonathan Schoop. But it would be a classic case of selling low on Schoop, who's hitting .202 with a .596 OPS.

If the situation seems too daunting for comfort, the Orioles can take heart in the example set by the 2015 Philadelphia Phillies. General manager Ruben Amaro entered the season in lame-duck mode, but he made a series of trades to inject some promising young talent into the system. Over a seven-month span, Amaro sent Jimmy Rollins to the Dodgers for Zach Eflin, traded Jonathan Papelbon to Washington for Pivetta and dealt Cole Hamels to Texas for a package that included Jorge Alfaro, Nick Williams and Jerad Eickhoff.

On Sept. 10, 2015 -- six weeks after the Hamels deal -- the Phillies fired Amaro. He has since moved on to coach first base for the Red Sox and Mets, and he says the string of deals was possible because he stayed focused on the job and didn't worry about his future.

"I always felt throughout my tenure, regardless of whether I was going to be there or not, I wanted to make sure I was going to leave the organization in a better place," Amaro said. "It wasn't my job to stop doing my job. It was my job to continue doing my job until they told me not to do it anymore."

That same mantra applies to Duquette, who will keep plugging away amid a season that has been an ordeal from the first pitch.

"The direction of the club is pretty clear," Duquette said. "We're not in the pennant race. To me, it's always a question of, 'Are you going to try to win today or get better for tomorrow?' The organization had a competitive window, and now the window is changing. The job is pretty straightforward at this time of year: to move your veteran players and acquire younger players to help you get more competitive for your next campaigns."

Amid the nightly beatdowns, Showalter will keep making out lineup cards and Duquette will continue to field phone calls, and they'll leave the final call on their professional futures to ownership. It's all about survival in this lost season for the Orioles.