The Cubs are reaching a crucial point in their contention timeline. While the Major League club's window for another World Series trophy is open, the expiration date for the core group that has powered this impressive era on the North Side could be in the not-too-distant future.

Barring contract extensions -- which certainly cannot be ruled out -- the likes of Kris Bryant, Javier Báez, Anthony Rizzo and others could hit free agency by the 2022 or '23 seasons. The rotation will look different even before then. That makes this an important phase of drafting and developing for the Cubs, who want to sustain their big league success for as long as possible.

"We're well, well past the point of still congratulating ourselves and being happy about [past Draft success]," said Jason McLeod, the Cubs' senior vice president of player development and amateur scouting. "We need to be better. Obviously, with where were are with the timeframe of the Major League club, we know we need to infuse more talent both out of the Draft and internationally."

That process continues tonight.

The 2019 Draft takes place tonight through Wednesday, beginning with tonight's Draft preview show on MLB Network and MLB.com at 5 CT. MLB Network will broadcast the first 41 picks (Round 1 and Competitive Balance Round A), while MLB.com will stream all 78 picks on Day 1. MLB.com will also provide live pick-by-pick coverage of Rounds 3-10 on Day 2, beginning with a preview show at 12:30 p.m. ET. Then, Rounds 11-40 can be heard live on MLB.com on Day 3, beginning at noon ET.

Go to MLB.com/Draft to see the Top 200 Prospects list, mock drafts from MLB Pipeline analysts Jim Callis and Jonathan Mayo, the complete order of selection and more. And follow @MLBDraft on Twitter to see what Draft hopefuls, clubs and experts are saying.

Here’s how the Draft is shaping up for the Cubs, whose first selection is the 27th overall pick.

In about 50 words:

Past Draft successes have helped fuel the last four years, which include four playoff berths, three division titles, one World Series crown and more than 96 wins per season on average. As a result, the Cubs have adjusted to life late in the first round.

What they’re saying:

"When you're picking near the top or in the Top 10, like we did those first couple of years, you can really hone in your looks on a very select few players that you feel you're going to have a good chance at.

"At the same time, the work's still the same. I think you get a pretty decent feel throughout the spring, looking at the organization picking in front of you and historically what type of players that they like, and that year's talent pool. So, we still get a decent idea. I'd say maybe it's a pool of five players, let's say, at pick 27 that we have a pretty good idea we'll be selecting from. And then we do the appropriate work-up as if we were picking in the Top 10." -- McLeod

Who might they take?

Chicago's success with collegiate position players at the top of its Draft is no secret. For example, last year Chicago had the 24th pick and used it on Stanford shortstop Nico Hoerner. That explains why most mock Drafts have the Cubs picking a college hitter with their top overall pick. Both Jonathan Mayo and Jim Callis of MLB.com have pegged Texas A&M shortstop Braden Shewmake as a player who fits the mold for the North Siders. Mayo named Tulane third baseman Kody Hoese as an option in a recent mock, while Callis also listed North Carolina first baseman Michael Busch as a possibility in another mock.

Money matters:

Under the Collective Bargaining Agreement, each team has an allotted bonus pool equal to the sum of the values of that club's selections in the first 10 rounds of the Draft. The more picks a team has, and the earlier it picks, the larger the pool. The signing bonuses for a team's selections in the first 10 rounds, plus any bonus greater than $125,000 for a player taken after the 10th round, will apply toward the bonus-pool total.

Any team going up to five percent over its allotted pool will be taxed at a 75-percent rate on the overage. A team that overspends by 5-10 percent gets a 75-percent tax plus the loss of a first-round pick. A team that goes 10-15 percent over its pool amount will be hit with a 100-percent penalty on the overage and the loss of a first- and second-round pick. Any overage of 15 percent or more gets a 100-percent tax plus the loss of first-round picks in the next two Drafts.

This year, the Cubs have a pool of $5,826,900 to spend in the first 10 rounds, including $2,570,100 to spend on their first selection.

Shopping list:

Pitching, pitching, pitching. It has been and continues to be one of the main criticisms facing the Cubs during Theo Epstein's tenure as president of baseball operations. The Cubs built their core through position players, but they have yet to develop an impact pitcher out of an MLB Draft class. That need at the MLB level have mostly been filled via free agency and trades. The organization is excited about some of the arms currently climbing up the system, but adding more pitching depth remains a focus for the club. McLeod noted that this year's Draft class is weak on the college pitching front compared to previous years.

"I wouldn't say we're going to go in saying it's got to be a pitcher in the first round," McLeod said. "The way information has changed over the last couple of years, with all the clubs having more pitch data, using a lot more video, using a lot more metrics, certainly it helps. It changes the process of how you're evaluating players a little bit. But, organizationally, we know that we still, with pitching -- it's still an area of emphasis for us. But, as we approach the Draft, especially in the first round, obviously we're always going to get the most impact that we can out of that first pick."

Trend watch:

As noted, the Cubs have relied heavily upon college players in recent year. Chicago took outfielder Albert Almora Jr. as a prep star in 2012, but have been college-focused ever since at the top of the Draft. Including 2012, which was Epstein's first year at the helm, the Cubs have taken 78.1 percent college players within the Draft's first 10 rounds. Last year, though, Chicago did nab two high schoolers (Cole Roederer and Brennen Davis) in the second round.

"We're not wedded to a college player," McLeod said. "The last couple years, it's been a college guy that's been there. But, there have been high school players that we had right there with Nico and others that we've taken. It just so happened that the college guy is the one that fell in our lap."

The recent top picks:

2018: Nico Hoerner, SS (Double-A Tennessee; currently on the injured list with a wrist injury)
2017: Brendon Little, LHP (extended spring camp)
2016: No first-round or second-round picks
2015: Ian Happ, OF (Triple-A Iowa)
2014: Kyle Schwarber, OF (Cubs)