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(Yahoo!) New Chicago Cubs manager Joe Maddon is the most popular man at these MLB Winter Meetings. Jon Lester is the most talked-about free agent at the meetings. They combined in spectacular fashion Tuesday night when we learned the Cubs had signed Lester for six years and $155 million.

Shortly after, Maddon — used to the cost-effective strategies of his old gig with the Tampa Bay Rays — felt like he'd just struck it rich.

“It’s not often you get to win the lottery,” Maddon said in front of a throng of reporters in the lobby of the Manchester Grand Hyatt. “We won the baseball lottery so far this year. Now it’s up to us to put it into effect."


That last part is key. Now it's time to produce. We're about four months away from baseball games actually being played, but the pressure is already on for the Cubs. It's one thing to win the offseason — ask the Toronto Blue Jays or Texas Rangers of the past couple years — it's another thing entirely to actually win games.

But the Cubs' plan is coming together. They brought Maddon in to manage after he opted out of his contract with the Tampa Bay Rays. They traded for catcher Miguel Montero earlier Tuesday. Then they signed Lester, the second-biggest fish on the free-agent market behind Max Scherzer. All the while, back in Chicago, the first phase of the Wrigley Field renovation is going on. It's quite fitting. Makeovers everywhere.

As enamoring as it all is, let's remember these Cubs aren't a team needing one last piece to get over the hump. They finished 73-89 in 2014, last in the NL Central. It was the same story the two years before that, just with higher loss totals. 

That's all in the past now. The North Side is waking up Wednesday in the future.

Many of the young prospects the Cubs had stockpiled arrived in the big leagues last year, players such as Javier Baez and Jorge Soler. Slugger Kris Bryant is on the way next year. Addison Russell is still coming too. Anthony Rizzo had a 32-homer breakout season in 2014. They've got Jake Arrieta and Kyle Hendricks in their rotation to go along with Lester. Yes, things are falling into place.

“This definitely propels us into Plan A, which is kind of neat,” Maddon said. “It’s a big day for us, moving forward. It really brings a lot of different factors together. It’s very exciting.”

The Cubs would still be well served to add another quality starting pitcher. But whether they do or not, the expectations have been raised and they're not going back down. The Cubs aren't lovable losers anymore. Now they're expected win.

Nobody needs to remind Maddon or Lester or anybody wearing blue in Chicago of the stakes. The Cubs haven't won a World Series since 1908. It's unfair to expect that in 2015. Their offense is still too young. But they've got Lester for six years, Maddon for five and all those prospects maturing before our eyes.

The Cubs have their marching orders. Go forth and win. Disappointment won't be accepted anymore.

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