After over a century of losing, the North Side of Chicago finally has something to be excited for. Over the past couple of seasons, Theo Epstein and Co. have been working to build the next powerhouse in baseball. While on the surface it may seem he hasn’t done much yet, a talented pool of prospects are on their way up to The Show. Players like Kris Bryant and Addison Russell lead that charge and now with some recent acquisitions, the Cubs are now even closer to contending.

In the biggest signing of the offseason so far, the Cubs inked Jon Lester to a six-year, $155 million deal with a $25 million option for a 7th year and a $30 million signing bonus. At $25.8 million a year, Lester becomes the 2nd highest pitcher paid pitcher annually. What a deal. It’s clear how good Lester is. With a career 116-67 record, a 3.48 ERA, and 1.28 WHIP, he is one of baseball’s better pitchers. Not only is he an ace in the regular season, he is one of baseball’s best postseason pitchers around. In 14 games, he boasts a 2.57 ERA with a minuscule 1.07 WHIP. Plus there’s those two World Series rings.

His newest batterymate will be Miguel Montero, who the Cubs just acquired from the D-Backs. Montero, once an All-Star, is a career .264 hitter with a very strong .342 OBP. Just a couple of years ago, Montero was one of the best catchers in baseball. From 2011-2012, the left-handed hitter averaged a .284 AVG, 16 HR, 87 RBI, 30 doubles, and a .372 OBP. Since 2012, he has come back down to earth, just hitting .237 since then. While his bat has been suspect as of late, he is known as a very strong defender behind home plate and is an excellent pitch framer. He is due $40 million over the next three seasons.

Lastly, the Cubs just brought back right-hander Jason Hammel, who pitched brilliantly during his time in Chicago. While he has been a below-average starter in the Majors for most of his career, he thrived with the Cubs, going 8-5 with a 2.98 ERA in 17 starts with them in 2014. With that being said, he does have a career 4.60 ERA and has never won more than 10 games in a season, but he might have found his niche with the North Siders.

Lester is a huge addition for the Cubs moving forward. Montero and Hammel are also solid upgrades at their positions. They will certainly help this team. With that being said, it’s important to look at this from a different perspective. The Cubs finished 73-89 last season, 16 games under .500. That is quite a few games to make up. I’m not going to compare these two, but hear me out; Lester fills the shoes of last year’s Samardzija and Hammel. I know, Lester is better than the two of them, but during their time with the Cubs last season, Samardzija and Hammel were very, very good. Extremely underrated. Their two performances outweigh what Lester can do on his own. With Samardzija gone and that the likelihood of Hammel repeating last year is slim, Lester is, for a lack of a better term, a filler.

Let’s not forget, Samardzija went 2-7 with the Cubs last year with a 2.83 ERA. Hammel went 8-5 with a 2.98 ERA. Put the two together and you get 34 starts, 216.2 IP, and a 2.91 ERA. Really good. You also get a 9-12 record. Why is that? While the Cubs didn’t have a dominant rotation, they weren’t too shabby either. On the other hand, they had one of the worst offenses in baseball. They finished 26th in runs scored, 27th in average, and 28th in OBP. I’m sorry, but Jon Lester won’t help in those categories. If all things remain equal offensively and you get 34 starts (career high), 216.2 IP (2nd highest), and a 2.91 ERA (2nd best) from Lester, you are back to square one. And no offense to Lester, but that’s asking for a lot. He has thrown the 5th most pitches since 2008 and he isn’t getting any younger.

Now don’t get me wrong. The Lester signing for the Cubs is a great deal for both sides. But, hold off on the 2015 World Series predictions. The Cubs now have an ace, but there are a lot of question marks after that. Jake Arieta was very good last season and Kyle Hendricks had a nice run with the Cubs as well. Can they continue that performance? Even after those questions marks, they still have Edwin Jackson, who had a 6.33 ERA last season. Lester certainly helps, but there’s still a lot of work to do.

The X-factor for the Cubs will be this offense. Unless they make a big play for Justin Upton or another superstar (which certainly could happen), they are relying on Rizzo and their core group of prospects to lead the offense. Rizzo is a superstar and will continue to rake at Wrigley. He is a great baseball player. Starlin Castro has proved to be a very good Major League hitter. After that, the question marks remain. This team will rely on the production of Javier Baez, Jorge Soler, and Arismendy Alcantara. In the 24 games Soler played, he hit .292 with five HR, 20 RBI, .330 OBP, and a .573 slugging percentage. Very good numbers, but can he continue that success? As for Baez and Alcantara, they definitely had their struggles at the big league level. Alcantara hit .205 with a .254 OBP in 70 games and struck out 93 times in 278 AB. Baez hit only hit .169 with a .227 OBP in 52 games and struck out 95 times in only 213 AB. That’s pretty bad.

I realize Baez was/is one of the top prospects in baseball, but he is striking out at a very alarming rate. Prospects with high strikeout rates are very difficult to project, because they have gone so far with their specific swing. Baez has dominated with his long swing for so long, why would he ever change it when he was soaring through their system? Unfortunately when he got to the Majors, that swing caught up to him. Sure, he has a ton of pop. Sure, he can hit quite a few 450-foot bombs. But will he be the next Mark Reynolds?

The nice thing for the Cubs is this – let’s say Baez is a total bust. We find out in 3-4 years he flames out and has a hard time finding a job. Very hypothetical but roll with me here. Their prospect pool is loaded. I haven’t even begun talking about Kris Bryant or Addison Russell yet. If Baez is a total dud, it isn’t the end of the world for this team. They have a lot of other talent coming up through the ranks. I will be honest with you, I don’t think Baez is “all that”. I don’t think he will be a superstar like many predict.

On the other hand, there’s Kris Bryant. .325 AVG, 43 HR, 110 RBI, 34 doubles, 15 stolen bases, .438 OBP last season in Double and Triple-A. Out of this world numbers. This kid is and will be the real deal. No ifs, ands, or buts. He was the Minor League Player of the Year. Just the year before, he was the College Baseball News Player of the Year. The only other player to ever do that was Alex Gordon and he has panned out just fine. It will be interesting to see what the Cubs do with Bryant to start 2015. Luis Valbuena, who is not a superstar by any means, did put a solid campaign together for the Cubs in 2014. He hit .249 with 16 HR, 51 RBI, 33 doubles, four triples, and a .341 OBP. I know Bryant will eventually surpass him on the depth chart, but it is all a matter of when.

If you thought Bryant was the Cubs’ only top prospect, you are wrong. In comes Addison Russell, the shortstop acquired from the Oakland A’s in the Jeff Samardzija trade last season. Russell, who will turn 21 in January, is another one of the top prospects in all of baseball. The former 1st round pick out of Pace High School (FL) is a career .300 hitter in 233 minor league games. Scouts believe he could hit between 25-30 home runs a year at the Major League level and be a Gold Glove shortstop as well.1 On top of that, he has plus speed and could steal around 20 bases a year as well. Not bad for a guy who can’t legally go to bars yet.

So, what’s next for this team? Obviously Theo and Co. aren’t done wheeling and dealing yet. By adding Joe Maddon and Jon Lester this offseason, this team is expected, and will have a lot of pressure, to compete in 2015. No more “next season” for the Cubs. The clock has begun to tick. The Cubs must make a splash somewhere else this offseason. Lester is a big move, but they cannot stop there. Like I mentioned earlier, their rotation is, in essence, back to where it was last year. Their young bats (Baez, Soler, Alcantara, Bryant) have to step up and become the difference makers they are expected to be.

Let me put my GM hat on for a minute. Starlin Castro is under one of the prettiest contracts in baseball. He is only due $43 million for the next five years, with a $16 million club option for the 6th. Even though he is pretty poor at shortstop, his bat is very valuable. Especially at only $8.6 million for the next five years. His name has been rumored in many different trade possibilities, but I don’t see it happening. With that kind of contract, he is extremely valuable. He hit .292 last season with 14 HR, 65 RBI, 33 doubles, and a .339 OBP. Also, he will only be 25 once the season starts. No need to trade a guy with that type of team control and those numbers.

That leads me to the logjam they have at the 2B/SS position. Castro, Baez, Russell. Basically, someone has to go. At least eventually. I don’t think the Cubs want to move Castro and after acquiring Russell in a trade last year, I feel like they are very high on him as well. We end up with Javier Baez, the odd man out. It’s worth noting that Theo Epstein was not the one to draft Baez. He came into the picture later that year. I point that out because there is no emotional attachment between him and Baez.

What I’m getting at is they should trade Javier Baez. Sell high on one of the top prospects in the league. I think Addison Russell is a much more impressive prospect than Baez and also projects to be an everyday shortstop. You package Baez, his ridiculously long swing, his extremely high strikeout rate, and his poor defense for let’s say a Cole Hamels or Justin Upton. Now we’re talking. Russell, when the time is right, can come up and take over at shortstop and Castro moves over to 2B. In the mean time, Tommy La Stella plays 2B for the Cubs. It all makes sense.

All I know is that Theo isn’t done. He plays in one of the toughest divisions in baseball and even with the moves the Cubs have made, they still finish 3rd in that division. They need to make another move or two and then have Kris Bryant make his way to the Hall of Fame (I kid). But seriously, this team isn’t great. Yet. But they are getting pretty damn close.