The Chicago Cubs have done it. We have finally left the all-familiar friend zone of free agency, wherein every girl used to flirt but never commit.

King Theo and his merry band of brothers finally scored the hottest girl at the party, and hopefully all her friends flock behind her. Everything I’ve penned below you’re probably already aware of, but as a lifelong Chicago Cubs fan I just had to express my excitement through words.

It’s only December 11th, but waking up yesterday morning had more of that December 25th type of feel. In what may go down as the most influential free agent signing the organization has ever seen, the Cubs made right by inking two-time World Series champion Jon Lester to a six-year, $155 million contract that could potentially be worth up to $170 million.

That’s a massive contract only justified by how monumental of a day it was for the Cubs.

Nearly simultaneously, the Cubs were executing a trade that nabbed them a great two-way player in catcher Miguel Montero, on top of returning Jason Hammel to the rotation two days prior.

This effectively speeds up the front office’s plan by a year or two and is a big hint that the front office deems the Cubs ‘ready to win now.’

The farm system, as we all know, is loaded with a bevy of talented bats ready to break into majors this year or next. But the Cubs were low on pitching and needed a vast upgrade that would bump Jake Arrieta down to the two hole in the rotation. With plenty of options this offseason, Theo set his sights on the number one option, Jon Lester.

Jon Lester is coming off the best season of his career, so Epstein and the Cubs knew it would require a big-time offer to dispel the recency bias that gives teams like Boston and San Francisco (the last two World Series champs) an advantage. Lester has connections to both Chicago and Boston so it was no surprise his decision ultimately came down to those two.

However, the signal it sent to the North Side of Chicago and its faithful fans was much larger than the amount of cash coming out of the Ricketts’ pockets.

What Jed Hoyer and Theo Epstein did was brilliant. If they happened to have missed out on Jon Lester, Cub fans would have come back to reality. Everyone would patted them on the back and told them thanks for trying, we can hold on another year.

With the Cubs not really expecting to compete for a pennant, nobody would have batted an eye and people would have watched the 2015 in anticipation for next offseason’s crop of marquee free agent pitchers.

It would have eased Wrigleyville into the 2015 season, knowing the front office is serious about this team and they are on the precipice of winning.

But that was all if we lost the Lester sweepstakes.

The Cubs took advantage of a situation that they would have never even been in until Boston played their cards so damn bad. It was basically public knowledge that Jon Lester was seeking more than five years and $100 million. He openly said it last season, and admitted that he was more than willing to take a hometown discount if it fit within his initial parameters.

Boston responded with a lowball offer of four-years, $70 million and Lester cut off all negotiations.

His eventual signing in Chicago has vaulted the Cubs into Plan A-plus mode. With the addition of Lester, the pitching staff is almost set with Arrieta, Hammel, and any combination of Kyle Hendricks, Travis Wood, or Tsuyoshi Wada bringing up the rear.

Look for this move to start a domino effect. Obviously, the teams who came up empty in the Lester stakes are already running to their Plan B faster than a freshman sorority girl to free alcohol at a frat house.

Had they missed out on Lester you would have seen the Cubs take a more cautious approach. No overspending or pressing the issue. No chasing big name players because they were not needed at this point in the rebuilding process. Although the Cubs have no plans on spending anything near to another $100+ million dollar contract, I wouldn’t be surprised to see a couple more “role players” added. Players who could end up playing a big part in 2015.

Another thing this should tell you is that come July, the Chicago Cubs will actually be buyers at the deadline. No more wondering if your favorite player is going to be on the market. If we can be in the thick of a very tough Central Division race, that’s when Theo does Theo.

I also wouldn’t dismiss a trade, either this offseason or early on, that will send either Starlin Castro or Javier Baez out and send top pitching back. It’s no secret that we are loaded in the middle infield, so keep an eye on that the next couple of months and early into next season.

The talk is that the Cubs are looking to add a guy who can be a great fit in the clubhouse, like outfielder Jonny Gomes- a former favorite of manager Joe Maddon. They already got their left-handed hitting catcher in Montero, and after watching Theo in his days with Boston, when he decides to go for it he doesn’t fuck around.

We are obviously all in this season and for many years to come. With the Cardinals being the Cardinals and the Southside having an exciting offseason as well, the Cubs are ready to renew rivalries and take the 2015 season by storm.

Sit back, grab an Old-Style, and get ready for the 2015 baseball season. It’s going to be a fun one.

(Featured Image courtesy of Keith Allison)