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A Few Thoughts About The Meaning Of Jon Lester

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In advance of the news conference introducing Jon Lester as the newest Chicago Cub, here's how it feels.

Anthony Gruppuso-USA TODAY Sports

At 1 p.m. CT Monday afternoon, lefthanded pitcher Jon Lester will step before a microphone at Spiaggia Restaurant on Michigan Avenue and speak his first words to the media as a member of the Chicago Cubs.

Think about that location for a moment. Spiggia, an upscale Italian restaurant. Compare that to the Cubby Bear, where Joe Maddon was introduced as Cubs manager a month ago. With Wrigley Field unavailable for news conferences due to construction, the Cubs are having to get creative with news-conference venues.

It likely doesn't mean anything in particular that the man who has signed the biggest-dollar contract in Cubs history is being introduced at a restaurant where, if you were so inclined, you could order a free-range veal chop with rutabaga, radish, apple, hazelnut and coriander that'll set you back $68. (Link opens .pdf)

But the fact that the Chicago Cubs have opened up their wallets and sprung for not only a top-priced, top-of-the-rotation free-agent pitcher, but a catcher to go along with him and hints that more spending is coming puts the team in a far different mindset than they've been over the last three years.

Some of you think that I'm against what Theo Epstein has done to revamp the farm system of the Cubs since he's been here. That's simply false. It was clear that housecleaning was needed after the collapse of the 2007-08 division champions and some failed attempts to patch them by Jim Hendry while the pipeline of young talent collapsed. In fact, I'll say here and now that Theo has done a fine job of drafting and evaluating young talent. The three years' worth of drafts under Theo (and the prize left to him by Hendry, Javier Baez) has begun to bear fruit, with Baez, Arismendy Alcantara (another Hendry holdover) and Jorge Soler making their big-league debuts last year and all having some success, and Kris Bryant next in line to show up at Wrigley Field shortly after the 2015 season begins.

There was a time when people would ask me when the Cubs would contend again, and my stock answer was "2018." That was the way the timetable appeared to me when guys like Justin Germano and Jason Berken were starting some Cubs games, Rule 5 picks were being wasted on the likes of Lendy Castillo, and the dour Dale Sveum was managing the club.

But 2014 represented a turning point, not just on the field but when Maddon was providentially dropped into the Cubs' laps. The hire of Maddon, to me, was a signal that the Cubs were going to be serious about competing not in 2018, but three years earlier.

We all know about the intrigues and back-and-forths that led to the reports last week that Lester had been signed. He chose the Cubs over:

  • His former team, with which he had longterm pleasant associations, a history of winning and a place his family liked
  • A team that has won three World Series in the last five years and offered him the hope of more such events
  • And, a team that seemingly was willing to throw untold sums of money at him, grabbing him no matter the cost

The Cubs beat out the Red Sox, Giants and Dodgers and got Lester to come to Chicago. Yes, the money certainly was competitive, but the prior relationship between Theo and Lester and the chance to create something historic in Chicago apparently won out and has brought Lester to the Cubs for the next six, maybe seven years. By the end of the contract, it might be seen as an albatross.

I said this often about the eight-year deal Alfonso Soriano signed in November 2006, and it applies to Lester's contract as well: If Lester helps lead the Cubs to a World Series win in the first two or three years of this deal, not one of us will care about the rest of it.

Of course, Lester can't do this himself. He's a starting pitcher who will have an impact on 32, maybe 33 games a season, about 20 percent of the schedule. But the team put together by Theo & Co. is clearly designed to contend in 2015. But beyond 2015, the organization Theo & Co. has amassed over the last three seasons ought to be able to be right there with the best teams in baseball for many, many years going forward.

For that, I'm glad. The last three years contained a lot of pain for Cubs fans watching the major-league team. I've said here on a number of occasions that I'm not a fan of the Iowa Cubs, the Tennessee Smokies, or the various other lower-level franchises, some of whose locations will change in 2015. That doesn't mean I haven't been interested in the players that are beginning to filter into Wrigley Field from those levels. At last, last year some of the fruits of those "waves" of talent began to arrive in the big leagues and more will come this year and in future years.

The rebuild -- or, actually, "build," because the Cubs farm system has never had the talent level it does now -- continues. But the signing of Jon Lester announces to the baseball world that the Chicago Cubs are ready to compete for a playoff spot. Now.

For which I couldn't be happier. It's a great time to be a Cubs fan. Can't wait for spring training and Opening Day. I'll have more here after the news conference.