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Winter meetings winners (Windy City) and losers (defending champs)

Winners (Cubs, White Sox) and losers (Giants, Orioles) from a very busy winter meetings.

In many ways, an insane week of winter meetings in San Diego leaves us with more questions than answers. Is this just the beginning of the madness in Hollywood? Are the Phillies finally ready for a complete dismantling? Are the White Sox the most improved team in Chicago — and in all of baseball? Has Andrew Friedman lost his mind?

Yes, it’s true: This was one of the craziest and most compelling winter meetings in recent memory. A team that began the offseason at 40-1 to win the 2015 World Series moved, in a matter of hours, to among the Vegas favorites, at 12-1. A team that won 94 games and finished with the fourth best record in baseball in 2014 was the most aggressive team of the week and will be barely recognizable in 2015. A team that won 73 games last season and began the week as an afterthought improved itself more than any other club.

But the Cubs, Dodgers and White Sox aren't the only teams that made noise this week, and the offseason is far from over. A pair of aces remain on the free agent market and there are still big chips that could be dealt, including an ace in Philly (Cole Hamels to the Dodgers?) and an All-Star slugger in Atlanta (is Justin Upton bound for Seattle?).

While a few teams took big steps forward, others did what a record-number of players did this past season: struck out. Herewith, the biggest winners and losers of the 2014 winter meetings:

WINNER: The city of Chicago

Three Strikes: Aggressive White Sox are offseason's biggest surprise

The most improved team so far this offseason is from the Windy City, but it’s not the club from the North Side. After a fourth-place finish in the AL Central in which they posted the second worst run differential in the league, the White Sox turned themselves into a contender with a flurry of shrewd moves by general manager Rick Hahn, the man who struck a pair of smart deals a year ago by signing Cuban defector Jose Abreu to power the middle of the team's lineup and trading for outfielder Adam Eaton. The White Sox looked like they were possibly a few seasons away from contending, but maybe Hahn sensed an opportunity in the AL Central after the Tigers limped into the offseason looking more vulnerable than they have in years, and the Royals will take a step back if, as expected, they lose ace James Shields in free agency.

Jeff Samardzija, acquired in a trade with the A's, turns 30 in January, but he doesn’t carry the typical mileage of a pitcher his age — as a football star at Notre Dame, he didn’t have the workload of a typical collegiate pitcher, and he didn't even throw 140 innings as a professional until two years ago. He was an ace caliber pitcher in 2014, and it wouldn’t be terribly shocking if he and lefthander Chris Sale emerged as the most dominant starting duo in the AL next year. Chicago's bullpen has been a disaster, so overpaying for closer David Robertson — who got four years and $46 million — makes a lot of sense. With Sale and Abreu in their primes, the White Sox believe they can win now. And in this age of the 10-team playoff format, that’s not delusional — even for a team coming off a 73-win season.

Speaking of 73-win teams: Across town, the Cubs' last-place finish in 2014 offered slivers of hope as their talented core of young position players came of age. Rising stars Javier Baez, Anthony Rizzo and Jorge Soler made the team much more entertaining than a losing club should be, and minor league home run king Kris Bryant announced himself as the best prospect in the game. The Cubs took a big step forward with last month's hiring of manager Joe Maddon, then went out earlier this week and acquired the underrated Miguel Montero at catcher. Still, the roster was starved for top-end pitching — that is, until they went out and landed Jon Lester.

World Series hope abounds, and more lessons from winter meetings

This game-changing moment for the franchise was long expected as it attempts to transition from rebuilding mode to win-now mode. Lester, a three-time All-Star coming off a season with a career high 155 ERA+, is much more than a one-year upgrade. In fact, with his cutter and a move to the National League, Lester should be a beast for years to come in Chicago. As for 2015, the Cubs are still one elite pitcher from being a true contender in the NL Central, where the Cardinals and Pirates remain the teams to beat. The Cubs might very well wait until the trade deadline, or next winter, to add that next key arm, though they have the money to land Shields, and with their surplus of dazzling young hitters, they could also swing a trade for an ace like Hamels. In other words, Theo Epstein and Co. are only getting started.

It’s official: The Cubs are the most fascinating team in baseball.

Free agent tracker: Keep up to date with the latest moves

LOSER: Giants

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After missing out on Lester, the defending World Series champions could go hard after Shields — the righthander would be a perfect fit in AT&T Park — though they still probably need two starting pitchers to replace Jake Peavy and Ryan Vogelsong in the rotation, and they still need a third baseman and a big bat to replace Pablo Sandoval in the lineup. Their big rivals down the California coast in Los Angeles, meanwhile, have been on a rampage that’s positioning them to contend in 2015 and well beyond. The offseason is still far from over, but San Francisco has to be disappointed about its week in San Diego.

WINNER: Next year's free-agent starters

Winter meetings roundup: Tigers get Cespedes, Marlins snag Latos

With Lester off the market, all eyes are on Max Scherzer, who turned down $144 million a year ago in what’s now looking like a brilliant gamble. Scherzer is reportedly seeking a $200 million deal, and the righthander who began this offseason as the best pitcher on the market might be in position to get it. The price on elite starting pitching has been set with the Cubs’ $155 million contract with Lester, and the big winners from that deal aren’t limited to this winter’s remaining crop of free agents. Consider the impressive group of starters set to hit the market after the 2015 season: Johnny Cueto, David Price and Jordan Zimmermann, all of whom just saw their asking prices go up like the Endurance spacecraft heading toward a wormhole.

LOSER: Royals

Billy Butler is gone and they're unlikely to pay James Shields what it would take to keep him. Kansas City brought in Kendrys Morales, who slugged .338 last season, to bat in the middle of its order. The Royals are competing in a division that’s only getting better with the hungry Tigers, the rising White Sox and the now quietly improved Indians and Twins. Kansas City's magical October ride seems like a while ago, doesn't it?

WINNER: Dodgers

Matt Kemp trade a sign that even Dodgers are playing by new rules

Are they better? Who knows? What's clear is this: Los Angeles added depth, defense and financial flexibility — and did so without trading away any of its top prospects. When they’re healthy, Matt Kemp and Hanley Ramirez are two of the best hitters on the planet, but even now that they're gone, the Dodgers are in a better position than they were a week ago. The organization is more financially streamlined, and top prospects Joc Pederson and Corey Seager now have a clear path to everyday jobs. After winning 94 games in 2014, L.A. will have a new centerfielder (likely Pederson), second baseman (Howie Kendrick, acquired in a trade with the Angels), shortstop (Jimmy Rollins, who came over from the Phillies, will hold down the job until Seager is ready) and No. 4 starter (Brandon McCarthy). That’s how things stand today — and it’s still just December.

LOSER: Orioles

New front office puts its stamp on Dodgers with flurry of acquisitions

Baltimore won 96 games last season and took the AL East by 12 games, but after losing Nelson Cruz, Nick Markakis and Andrew Miller in free agency, its biggest moves this week were adding righthanded pitchers Jason Garcia and Logan Verrett from the Rule 5 draft. GM Dan Duquette always seems to find a way to unearth value in the market, and there’s still time, but the Orioles have a lot of work to do to position themselves in a division where the Red Sox (who have added Ramirez and Sandoval to their lineup and Wade Miley, Justin Masterson and Rick Porcello to their rotation) and Blue Jays (who signed catcher Russell Martin and traded for third baseman Josh Donaldson) have improved notably this offseason.

WINNER: Marlins

You can argue that giving up pitcher Andrew Heaney, a top-10 pick in 2012, and infielder/outfielder Enrique Hernandez was too much for second baseman Dee Gordon, and you wouldn’t be wrong. The Dodgers sold high on Gordon, an All-Star last year whose performance fell off notably in the second half, and it’s not clear that his addition alone makes Miami better. The acquisition of Mat Latos, however, does make the Fish dangerous in the NL East. Remember, this was a team that wasn’t far from contention last season, sitting just 4 1/2 games out of a wild-card spot when Giancarlo Stanton went down with a season-ending injury in mid-September.

By the end of next season, Miami's rotation could have a top three of Jose Fernandez (slated to return from Tommy John surgery in July), Latos and Henderson Alvarez. In the final weeks of September, as the 2015 races are heating up, that could be one of the best 1-2-3 combinations in the league.