Entering last offseason, the Orioles were at a crossroads. New club president Andy MacPhail decided an overhaul was needed.
MacPhail upgraded the young talent base by dealing Miguel Tejada and Erik Bedard for 10 players, including six who received time with the big league club this year.
This was supposed to be a season in which the club evaluated what it had in its system. Unfortunately for the organization, the majority of young players either failed the test or received an incomplete grade.
Because of elbow problems, starter Adam Loewen will never pitch again. Garrett Olson, Radhames Liz and Brian Burres struggled in their opportunities. Infielders Luis Hernandez and Freddie Bynum washed out and were removed from the 40-man roster. And corner infielder Scott Moore slid down the depth chart after an injury-riddled minor league season.
Instead of filling some glaring holes, the Orioles might have created more unanswered questions heading into this winter.
Consider that eight Orioles had at least 450 at-bats in 2008 and only two are younger than 30. Of the other six, one is a free agent this winter (Kevin Millar) and four others (Brian Roberts, Melvin Mora, Aubrey Huff and Ramon Hernandez) are eligible for free agency after 2009.
Furthermore, Jeremy Guthrie is the only starting pitcher who can be confidently put into next year's rotation and the club's four best relievers have dealt with injuries.
So there are plenty of issues MacPhail will have to address this winter. Here are 10 of the most pressing.
What happens with Roberts?
The team's leadoff hitter and spark plug had another highly productive season and certainly will draw significant interest as a free agent after 2009. An Oriole his entire career, Roberts has said publicly that he loves playing in Baltimore, but you have to wonder whether the continual losing has punched his ticket for free agency.
"I have a contract for next year, so the only way [he's elsewhere in 2009] is if they do something," Roberts said. "I don't really have any control over that."
The Orioles will make a run at an extension with him this offseason, and if one can't be reached, he likely will be traded in the spring or at least by the end of July.
Will Markakis sign an extension?
This is probably the club's most important issue this winter, even bigger than keeping Roberts. Nick Markakis, 24, is clearly the team's best all-around player and its most concrete building block. He isn't a free agent until after the 2011 season, but this offseason is critical for extension talks.
If nothing gets done before Opening Day 2009, it wouldn't be surprising if his camp tabled talks and gambled on his health and talent for the next two seasons. The Orioles will need to pony up handsomely to get a long-term deal done with Markakis, but they know what he means to the organization, so expect them to make a legitimate offer.
Will the O's be players in free agency?
Despite being in continual rebuilding mode, the Orioles never fully strip down to the bare essentials. And this offseason likely will be no different. It's an intriguing and top-heavy free-agent class, and MacPhail has said that if a player can help the Orioles now and in the future, he'll be aggressive, even if the next couple of seasons don't project to be competitive ones. The main priority will be the rotation.
"We need to improve our starting pitching. No. 1," Orioles manager Dave Trembley said. "Our starting pitching needs to get better."
Who will be their top hitting target?
The Orioles' two biggest offensive needs are at shortstop and first base, especially since Millar could go elsewhere in 2009. There are multiple free-agent shortstop options, led by Orlando Cabrera of the Chicago White Sox. But there's no question the Orioles' No. 1 target will be Los Angeles Angels first baseman and Mount St. Joseph graduate Mark Teixeira. He is a top-five free agent and probably the only one who would consider coming here. The Orioles might not meet his asking price - certainly a $100 million-plus deal - but they'll kick the tires on the hometown hero.
Who will be their top pitching target?
The Orioles need at least three new starters, not just one, so they might seek a few lesser alternatives instead of one big name. Milwaukee's CC Sabathia leads a class that also includes Ben Sheets, his Brewers teammate; the Chicago Cubs' Ryan Dempster; and potentially Toronto Blue Jays right-hander A.J. Burnett.
Burnett has $24 million left on a deal with the Blue Jays but can opt out this winter. And with a tremendous second half, it's likely he will - and then command at least a four-year deal. The Orioles have a chance at Burnett because he makes his offseason home in Monkton. He's likely the only highly coveted free-agent pitcher who would seriously consider the Orioles.
What becomes of Cabrera?
After a poor second half that ended with a trip to the disabled list, Daniel Cabrera is eligible for arbitration this winter. The way the system works, the right-hander will command between $3 million and $5 million. It's possible the Orioles will decide that the investment isn't worth the pain of waiting for his development and will not tender him a contract.
Who will play shortstop?
It has been a revolving door since the Tejada trade. The club likes what it saw defensively from Juan Castro, but the light-hitting veteran is, at best, a fallback plan. Orlando Cabrera is the most intriguing, but Rafael Furcal and possibly Edgar Renteria will be available. Also, several players who have previously interested the Orioles - Adam Everett, David Eckstein, Cesar Izturis and Felipe Lopez - are options.
"Juan has done a good job for us filling in and being a productive defensive player," MacPhail said. "But quite honestly, his age would preclude him from being a long-term solution at that position. We're definitely going to have to look there."
Who will catch?
Hernandez has a year left on his contract and hit enough in the second half to perhaps create trade value this winter, which would open up a spot for top prospect Matt Wieters. The Orioles likely will pursue trade partners for Hernandez but might keep him around at least until next season's July 31 deadline.
"It's one of those things you'll know a lot more about in spring training," MacPhail said about Wieters' immediate future. "It's a pleasant thing to contemplate, but we really have other things that we need to do. Certainly [Wieters] has not demonstrated any difficulty going through the minor leagues, but he still has only one year of pro experience."
Are there other trade chips?
Mora would generate some interest, but he would be selective in lifting his no-trade contract. Huff had a great season and will be on the block, but he's viewed primarily as a designated hitter, which limits his suitors. Closer George Sherrill could be available if the team is confident that Chris Ray can bounce back from 2007 Tommy John elbow surgery.
What about the bullpen?
For the first time in three years, the Orioles are somewhat comfortable with their bullpen - which could be fairly deep if Ray, Sherrill, Jim Johnson and Matt Albers are healthy. Left-hander Jamie Walker was a colossal disappointment this season but is signed through 2009 and likely will get a chance to rebound.
"I always think you're going to look to improve it," Trembley said. "Our concern is those guys being healthy in spring training."