Offseason preview: 10 Orioles storylines to watch

Kurkjian predicts Orioles will lose Wieters, Davis (0:32)

Tim Kurkjian joins the Dan Le Batard Show to discuss what he expects to happen with the Baltimore Orioles this offseason. (0:32)

Baltimore Orioles fans don't need a Farmers' Almanac to tell them that winter in Charm City could feel especially cold this year. For the first time since 2011, the Birds failed to finish with a winning record. Now they're faced with the prospect of free agency robbing them of several big-name players who've been instrumental in the club's recent renaissance. Stock up on the firewood and hot chocolate, Baltimore -- it could be a long three months. Here are 10 things to watch for during the deep freeze:

1. Crush cashing in: Timing is everything. After an awful 2014 season that ended with him getting suspended for Adderall use, Chris Davis bounced back big time in 2015. The slugging first baseman -- who's now a free agent -- raised his OPS by 219 points, and his 47 home runs were most in the majors. It's the second time in three years he has led the league, and now he's set to cash in. As popular as Crush is in B-more, it's hard to imagine the O's letting him walk. Then again, given his price tag ($20 million a year isn't out of the question) and the Birds' frugality (their richest contract ever was $85 million for Adam Jones), it's even harder to imagine them keeping him.

2. Payday for O'Day: Last offseason, the Orioles lost Andrew Miller because other teams (i.e. the Yankees) were willing to pay the standout lefty reliever closer money. History might repeat itself this year with Darren O'Day. Although the 33-year old righty isn't quite the dominant force that Miller is, he has become one of the game's top setup men. This year, the submariner finished with a 1.52 ERA and was a first-time All-Star. He's also fantastic in the clubhouse. He'll no doubt draw lots of interest from potential suitors, including the Nationals, who have major bullpen issues and are geographically desirable for O'Day, whose wife is a Fox News correspondent based in D.C.

3. Wieters could end offer o-fer: Since 2012, when the qualifying offer was instituted as part of the new collective bargaining agreement, every one of the 34 players who received one has rejected it. Of the record 20 players who got qualifying offers this year, Matt Wieters is as good a bet as any to accept. His return to the field following 2014 Tommy John surgery was less than stellar. Taking the one-year, $15.8 million deal that accompanies a QO would give the 29-year old catcher a chance to regain some value before hitting the open market again after the 2016 season. That said, despite the health concerns and the down year, he's still the cream of this year's catcher crop. Wieters has until Friday to decide on the O's offer.

4. Weighin' Wei-Yin's worth: Since coming over from Taiwan, Wei-Yin Chen has been Baltimore's most consistent starter. As much sense as it makes to sign the 30-year old lefty, the Orioles have never been big players in the free-agent pitching market. The richest contract they've ever awarded a hurler is the $50 million over four years that they gave Ubaldo Jimenez two years ago. And it's not as if that has worked out super-dee super. Between that and the need to budget for a potential run at Davis, it wouldn't be a surprise to see Chen, who's repped by Scott Boras and could command a deal similar to one that Jimenez got, fly the Birds' coup.

5. The not big four: Aside from the quartet of big fish the Orioles stand to lose, Gerardo Parra and Steve Pearce are also free agents. Pearce had a down year marred by injury and Parra underwhelmed after coming over from Milwaukee in a deadline deal, so the price tag on both should be manageable for Baltimore. Buck Showalter loves the flexibility afforded him by Pearce, a first baseman/outfielder who even started 16 games at second base last season. Despite Parra's inconsistency after joining the American League, he's a two-time Gold Glove outfielder with decent pop and plate discipline. It wouldn't be a surprise to see either -- or both -- of these guys back in black and orange.

6. Lacking at leadoff: Baltimore hasn't had a legit everyday leadoff hitter since Brian Roberts in 2009. Manny Machado was the team's most productive 1-hole hitter last season, but the Birds need him hitting third, where he belongs. And if Nolan Reimold's a leadoff man, then I'm Steven Matz's long-lost brother (for the record, I am not related to the Mets' hurler). Denard Span and Dexter Fowler are the best leadoff options available. Even though Span has health issues and Fowler whiffed 154 times last year, either would be a huge upgrade for an O's squad that, since the start of the 2010 season, ranks next-to-last in the American League in walks. Neither will come cheap.

7. Pay to play: Baltimore's $119 million payroll last season ranked 13th in the majors. Over the last three years, their average payroll of $106 million ranks 14th. So it's not as if they don't spend. They just don't spend what Orioles fans think they should -- or could. With a successful regional sports network like MASN, it seems as if owner Peter Angelos should have deeper pockets than he appears to. With Davis hanging in the balance, maybe this is the year that Angelos finally plumps up the payroll.

8. Same page for Buck and Duke: Last offseason, it looked as if GM Dan Duquette might be headed to Toronto. Instead, he stayed put. Since then, there have been rumblings that Duquette and Showalter, who won executive of the year and manager of the year, respectively, in 2014, have been butting heads. If the Orioles are going to get what they need this offseason -- and to be clear, they need plenty -- the powers that be must work in concert.

9. In search of starting pitching: The performance by Baltimore starters in the second half of 2014 -- which helped propel the team to the American League Championship Series -- seemed a little too good to be true. And last season proved that it was. The Birds' rotation finished 2015 with a 4.52 ERA, second-worst in the American League. Jimenez was inconsistent. Miguel Gonzalez was injured and ineffective. Kevin Gausman was young and still is. Chris Tillman is a middle-of-the-rotation guy being asked to do front-of-the-rotation work. Chen might be gone. Thanks to deadline deals that cost the O's top prospects like Eduardo Rodriguez and Zach Davies, the Birds had to rely on stopgaps like Mike Wright and Tyler Wilson, both of whom weren't ready and might never be. All of which is to say, if the Orioles are going to compete in 2016, they'll either need to pony up for a top-tier free-agent starter, or get lucky with a second-tier signing. Or both.

10. Young guns not firing: Dylan Bundy was the No. 4 overall pick in 2011. Hunter Harvey was the 22nd overall pick in 2013. Both were considered can't-miss pitching prospects, but injuries have limited them to a combined 282 innings as pros. Even worse, Harvey was shut down in September with elbow pain, and Bundy, who had Tommy John surgery in 2013, was scratched from a scheduled Arizona Fall League start on Monday because of right elbow tightness. If his and Harvey's health issues persist, it will only add to what's already likely to be a winter of discontent for O's fans.