You've got to know when to hold 'em, know when to fold'em, know when to walk away, and when not to bite on an aging player coming off a career year.  Here are five winners and five losers from the winter meetings in Indianapolis.

Winners

Baltimore Orioles

Kevin Millwood and $3 million for Chris Ray and a Rule 5 draft pick.  I'm not the biggest Millwood fan around, but are you kidding me?  This guy has averaged 190 innings per season over the past 11 years and a career ERA just a hair over 4.00.  People talk about the leadership he'll bring to a young rotation, which could indeed prove significant.  But he may also put together one of the best performances by an Orioles pitcher in the past decade.  I realize that's not saying a whole lot, but it's certainly worth $9 million and Chris Ray.

Although I like the move from Baltimore's perspective, I do not hate it from the Rangers'.  They sold Millwood after he greatly overachieved and immediately replaced him with the high-risk, high-reward Rich Harden.  Chris Ray has exhibited the unsettling trend of getting worse every year he has been in the majors, but Ben Snyder was probably the best player taken in the Rule 5 draft. The Texas bullpen unquestionably improved, the rotation may have improved pending Harden's health, and their financial ledger remains unchanged.  Not too shabby.

Chicago White Sox

If this were 2002, the White Sox would be clear favorites for the World Series, what with Andruw Jones, Omar Vizquel, and Mark Kotsay all on the squad.  Eight years later, that trio is more likely to provide comic relief than actual production.  J.J. Putz, however, could provide very real relief for an already impressive pitching staff.

Just two years ago, Putz had the best season of any major league reliever.  For the Sox to get him for $3 million - half of his 2009 salary - is a coup, particularly given the contracts some other lesser relievers received (more on that in the Losers section).  Between Bobby Jenks, Matt Thornton, and J.J. Putz, the Sox have three legitimate closers on the roster, plus Scott Linebrink is a damn impressive fourth option in a bullpen.  This could well be the best pen in the majors right now.

Detroit Tigers

Amid all of the hoopla over the Tigers trading a 30-homer, 20-stolen base player and one who had a 3.62 ERA in 214 innings last year, few people bothered to mention that neither Curtis Granderson nor Edwin Jackson are actually very good players.  Granderson had an OPS+ of 100 last year, always strikes out way too often, and is useless against left-handed pitching, as evidenced by his career .614 OPS against southpaws.  If not for his excellent defense and the fact that the Yankees gave up very little to get him, New York would appear on the Losers list.  Edwin Jackson is not only a huge injury risk next season based on his mid-90s fastball, 6.14 September ERA, and abusive workload, but he only had a fielding independent ERA of 4.34 in his supposed breakout 2009 season.

Austin Jackson is your typical overrated Yankees prospect, but he can likely approach a 100 OPS+, play solid defense, and even hit a left-handed pitcher once in a while.  Phil Coke is a serviceable southpaw, Daniel Schlereth is an unproven southpaw with huge upside, and Max Scherzer is one of the best young pitchers in the game.  Considering that the Tigers saved around $10 million, improved their roster for 2010, and swapped players approaching free agency for ones they can control for many years, this one mega-trade easily makes Detroit the biggest winners of the winter meetings.

Marco Scutaro

Okay, okay, he signed with the Red Sox just prior to the winter meetings, but he merits a mention.  Here's a 34-year old utility infielder who has never made more than $1.55 million in a single season.  He enjoys a breakout offensive season and somehow becomes a Type-A free agent, meaning that whoever signs him must part with a first- or second-round pick in next year's draft.  Scutaro still got a two-year, $12.5 million contract from the Boston Red Sox that even includes a dual option for 2012. 

I don't consider this a terrible move for the Red Sox.  A) Although Scutaro's offense last year was clearly a fluke, he could still put up good numbers aided by Fenway Park.  B) Scutaro is an excellent defender, which combined with even mediocre offense could still give the BoSox their best shortstop performance since the days of Nomar Garciaparra. C) Scutaro could be a complete bust and barely dent Boston's resources.  But for this former undrafted free agent, this is a terrific story, and it's hard not to cheer for him.

Washington Nationals

When the founders of Baseball Evolution took in a Washington Nationals game last summer, we were rather amused to find that Josh Willingham, Nyjer Morgan, and Tyler Clippard were their most heavily marketed players at the time.  Obviously, Adam Dunn's regular 400+ foot bombs need no marketing, Ryan Zimmerman may be a star in the making, and Stephen Strasburg will soon be the biggest thing in DC not named Obama, but there's no question that this new franchise can use a name player for a draw.

Enter Ivan Rodriguez.  I-Rod's days of not embarrassing himself at the plate are long since gone, and it's rarely a good idea to sign a 38-year old catcher to a two-year deal.   Nevertheless, he gives the Nationals leadership, marketability, and still one of the best defensive backstops in the game for just $3 million per season.  Pudge has a long history of spinning poor teams into good ones, and I wouldn't bet against that happening in Washington.

Losers

Arizona Diamondbacks

We covered a lot of this in the Tigers section, but the D-backs swapped out a phenom in Max Scherzer along with the second-best pitching prospect in their organization in Daniel Schlereth for two arms with huge question marks dangling on them.  Some say that Scherzer couldn't go deep into ballgames and was an injury waiting to happen, but his BAA was .228 in the 5th inning, .234 in the 6th, and .200 in the 7th last year.  Oh, and his FIP was 3.90, nearly half a run better than Jackson's.  And he's younger and under team control for much longer.

Granted, Ian Kennedy's 19-6 record, 1.95 ERA, and 10 K/9 in his minor league career are mighty impressive, but he still hasn't proven that he is more than a Quadruple-A pitcher.  And since he is coming off an injury himself, the reason behind dealing Scherzer becomes even more muddled.

Chicago Cubs

The Cubs are graded as losers because their position weakens every day they do not trade Milton Bradley.  There is no team out there that cannot live without Milton Bradley, whereas the Cubs simply cannot live with him.  The fact that no deal got done in Indy exposes Jim Hendry's lie that a half dozen teams are even interested in Bradley.  Also, without knowing exactly what bad contract the Cubs will have to assume in return for Bradley, they cannot really act on other trade or free agent avenues.

I hate to say this because it is such an annoyingly popular sentiment, but the Cubs should really consider bringing Mark DeRosa back into the fold.  His two best positions - second base and right field - are the Cubs' two weakest positions at the moment.  The acquisition of DeRosa would not preclude the Cubs from taking on another bad position player contract, because DeRosa can always shift to accommodate someone.  If they don't make a move now, they may well be stuck with the dregs of the free agent market once they finally deal or release Milton Bradley.

Houston Astros

What more can we say about Ed Wade?  He just threw $15 million at a merely serviceable reliever (Brandon Lyon, 3-years) and $4.5 million at a soon-to-be 35-year old third baseman with a career OBP of .293 (Pedro Feliz).  They also traded three prospects for Matt Lindstrom, who throws very hard, but isn't very good.  It seems to me that if you are a team coming off a 74-win season, you might want to trade for prospects, particularly when the free agents you bring in aren't any better than the ones you are losing (Jose Valverde, Miguel Tejada, LaTroy Hawkins, etc.).

There's no reason to believe that the Astros can't be the worst team in the National League next year.  If that happens, it may finally be enough to get Ed Wade fired, which would be the first step of a long process in rebuilding this once-proud franchise.

Milwaukee Brewers

I've averaged eight wins, 22 starts, 130 innings, and a 4.16 ERA over the past six seasons, and I turned 33 in August.  Who am I?  Randy Wolf, the deserving recipient of a three-year, $29.75 million contract, of course!  The one positive about Wolf is that his career year may not have been a product of Dodger Stadium, as he went 7-4 with a 2.78 ERA on the road.

I'm a career backup catcher who turns 39 in April and has a career .251 batting average.  Who am I?  Greg Zaun, the man making more than $2 million next season as the Brewers' starting catcher!  The one positive about Zaun is that he has hit better later in his career than he did when he was young, but he is a defensive liability that somehow hasn't played for a playoff team since 1997.  Expect that streak to continue in 2010. 

St. Louis Cardinals

Yes, a whopping fourth team in the NL Central that grades out a loser.  The Cardinals are losing a mob of free agents this winter, so clearly they needed to make several additions to offset their losses.  Committing $7.5 million (up to $9M with performance bonuses) to one erratic pitcher should not have been in the cards.  Sure, Dave Duncan can likely get the most out of Brad Penny, but what a waste of Dave Duncan!  Why not use him to resurrect a more affordable veteran pitcher or two?

This is a team that currently has no fifth starter, no left fielder, no third baseman, and an outfielder playing second base.  If this team wants to repeat as NL Central champs, they're going to need to spend some dough, because there is absolutely no help in their farm system.  Putting most of their eggs in a broken basket doesn't seem like such a hot idea.