It’s never easy to replace a General Manager, but given the current state of the Baltimore Orioles, I feel that it’s even more difficult usual. Don’t get me wrong, if Dan Duquette ends up becoming the Blue Jays CEO, his successor in Baltimore will be taking over an incredibly talented roster managed by one of the game’s best skippers, but there are a number of really important decisions he’ll be tasked with answering.

Such as:

1. Steve Pearce’s Arbitration Case

The O’s (and MLB Trade Rumors) have valued Steve Pearce‘s services at $2 million. Pearce filed for $5.4 million. That’s an enormous gap when it comes to arbitration cases, which means the two sides are likely headed for a hearing.

What are Pearce’s services worth to the Orioles? Last season he was second on the roster in WAR, 4.9, behind only face of the franchise Adam Jones. Is that repeatable? Or was it a fluke?

2. Chris Davis And Matt Wieters’ Future

Two more of Scott Boras’ clients are scheduled to hit the open market after the 2015 season. I’m talking of course about first baseman Chris Davis and catcher Matt Wieters. Both guys are coming off shortened seasons (adderall suspension for Davis, Tommy John surgery for Wieters) and will be highly motivated by an upcoming big pay day, but will either player be willing to sign an extension in season?

If history is any indicator, they’ll both wait for free agency — that’s what Boras advises to his clients.

If the Orioles are unable to re-sign Davis and Wieters, would they be better off moving one or both of them at the trade deadline? It’s a difficult decision to make for any GM, especially a new one who could be forced to answer that question in the midst of a playoff run.

3. Speaking Of Free Agents…

This winter, the Orioles had it easy. Nick Markakis, Nelson Cruz and Andrew Miller all hit the open market and found better deals elsewhere. Delmon Young re-signed.

Next offseason could be an entirely different story. Here are the players that are scheduled to become free agents after this season:

Not only are Chris Davis and Matt Wieters’ futures in question, but so too are the players listed above. An incoming GM would be tasked with determining the value of each player and deciding whether the Orioles should sign long-term, trade and let ’em walk.

4. Extension Candidates

Dan Duquette has invested in extensions with Adam Jones and J.J. Hardy during his tenure so far with the Orioles. If he leaves, his replacement will have decide which players the team should continue to grow around.

Chris Tillman is coming off his second straight 200+ inning season, pitching to a 3.34 ERA in 34 starts. The 26 year old is first year arbitration eligible next winter and under team control through 2018. Should the O’s look to buy out his arbitration years and sign him long-term?

What about Manny Machado? Sure, the kid is coming off his second knee surgery in two years, but when he’s on the field he’s proven to be a difference maker. He’s one of the game’s best defenders and was a 6.3 WAR player in 156 games for the Orioles in 2013. Are the Birds comfortable enough about his health to begin contract negotiations?

5. The Ever Changing AL East

No list of challenges for an Orioles GM would be complete without mentioning the AL East.

The last place Boston Red Sox have retooled this winter adding Pablo Sandoval, Hanley Ramirez, Rick Porcello, Wade Miley and Justin Masterson. I still think a top tier starter is on the way too.

The Yankees plucked away Andrew Miller acquired Nathan Eovaldi and Didi Gregorius and just last week were discussing the possibility of adding another starter.

How about the Toronto Blue Jays? They’ve brought in Russell Martin, Michael Saunders and Josh Donaldson. The Jays are also in pursuit of a closer to shore up the bullpen.

I hope Dan Duquette is the guy here in Baltimore for at least the four years remaining on his contract, but every indication is that Toronto isn’t going to let up until he’s north of the border calling the shots at the Rogers Centre. If a the Birds are forced to find a replacement, I hope he’s ready to answer these tough questions.

Featured Image Credit: Keith Allison