CHICAGO -- Two fewer wins. That's all that stands between the White Sox and Andrew Benintendi, the run-producing outfielder who MLBPipeline.com now ranks as the top prospect in baseball, a pure hitter who could be their Kristopher Bryant, their Carlos Correa.
Benintendi was coveted by the White Sox scouting staff long before his power surge that helped the Arkansas Razorbacks reach the 2015 College World Series. The better he hit, the more they feared they might lose him to a team with a higher pick. And sure enough, they did.
The Red Sox -- riding a crazy elevator of championships and last-place finishes -- took Benintendi with the seventh pick of the 2015 Draft, one before the White Sox. It's easy to forget now, but Boston won only 71 games in '14, the year after it celebrated its third World Series triumph in a decade; the woebegone White Sox, most recently in the postseason in 2008, finished '14 with 73 wins behind American League Rookie of the Year Award winner Jose Abreu.
That's water under the bridge. And it's too early to rule on how Carson Fulmer, the White Sox pick of that 2015 Draft, will pan out. But looking at the past, it's worth considering that the White Sox are taking two risks by holding onto Jose Quintana, who is lingering on the market, for the first half of the upcoming season.
The first is that Quintana's run of excellence will end with an injury, damaging his trade value. The second is that he'll pitch too well, keeping the White Sox in the middle of the pack for too long and hurting their position in the 2018 Draft.
That could be a big one for the White Sox, indeed.
Here's a road map that reveals how two painful seasons could be all Rick Hahn needs to get the South Siders back into the thick of things in the AL Central.
1. Trade Quintana before Opening Day
Hahn struck gold with his Chris Sale and Adam Eaton trades, landing impact bats in Yoan Moncada (MLBPipeline.com's No. 2 overall prospect) and 20-year-old center fielder Luis Alexander Basabe; possible front-line starters in Lucas Giolito (No. 12), Michael Kopech (No. 16) and Reynaldo Lopez (No. 46), among other pieces.

The White Sox general manager has been discussing Quintana trades nonstop since then, but he hasn't been able to duplicate the Sale/Eaton deals, as the Astros have refused to deal outfielder Kyle Tucker (Pipeline's No. 35 overall prospect) and the Dodgers have said no to all discussions involving Cody Bellinger (No. 13). Hahn is correct that he doesn't have to trade Quintana, but he'd be smart to take the best offer that's been on the table.
2. Add a big-time amateur bat
With the exception of Moncada, the White Sox big acquisitions this offseason were young arms. So with the 11th overall pick in the Draft, they should take one of a few exciting college hitters. Louisville first baseman Brendan McKay (MLBPipeline.com's seventh-ranked Draft prospect), Virginia first baseman Pavin Smith (No. 14) or Florida catcher J.J. Schwarz (No. 19) are advanced hitters who could be in the Majors in just a couple of years. The White Sox also should be very active at the international signing period -- when 11 of the other 29 teams are facing signing penalties -- targeting top talents like Cuban outfielder Luis Robert.
3. Be aggressive at the Trade Deadline
If they haven't already been traded, Todd Frazier, Player Page for David Robertson and Melky Cabrera could bring a nice return. Ditto recent free-agent signing Derek Holland, if Don Cooper is able to help him develop the consistency he's lacked through his career (62-50 with a 4.35 ERA over 985 innings).
4. Keeping adding kids as the advanced prospects arrive
Next offseason might be the time to consider dealing Abreu and Nate Jones, although only if the deals are right. They could be contributing players on the bounce-back team in 2019. With the roster cleaned out, the White Sox should be able to target positions of need and accumulate options through waiver claims and the signing of Minor League free agents.

The hope is that Carlos Rodon has hit his stride by 2018 and that Tim Anderson and Moncada are establishing themselves as a top up-the-middle combination. Prospects like reliever Nick Burdi, utility man Nick Delmonico and Adam Engel are earning their spots on a roster that is headed by the young rotation that includes Giolito, Fulmer, Lopez and Kopech.
5. Open up the wallet after 2018
Baseball is two years away from an epic free-agent class. The White Sox should be in great shape to participate heavily, especially if players like Moncada, Giolito, Kopech, Anderson, Rodon, Fulmer and a half-dozen acquired during 2017 and '18 have created a belief that the club is on its way to sustained success.
Manny Machado, Bryce Harper, Clayton Kershaw (assuming he uses his opt-out clause), Zach Britton and Andrew Miller head the class, which could also include Josh Donaldson, Daniel Murphy, Adam Jones, Andrew McCutchen, Hunter Pence and Jean Segura, among dozens of others. Imagine if the White Sox could start to cherry-pick other top free agents, like the Cubs did after they had assembled their young core.
Does this sound like a fever dream? Maybe, but who expected so many of the Red Sox's and Nationals' top prospects to be heading to Glendale, Ariz., for spring camp?
Two fewer wins in 2014 and Benintendi would have been there, too.