Chicago White Sox: 3 wild trade packages with Chicago Cubs

CHICAGO, IL - May 18: David Robertson of the Chicago Cubs pitches in a game against the Pittsburgh Pirates at Wrigley Field on May 18, 2022 in Chicago, Illinois. (Photo by Matt Dirksen/Getty Images)
CHICAGO, IL - May 18: David Robertson of the Chicago Cubs pitches in a game against the Pittsburgh Pirates at Wrigley Field on May 18, 2022 in Chicago, Illinois. (Photo by Matt Dirksen/Getty Images)
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The Chicago Cubs and Chicago White Sox have made a few different trades over the last five years or so. Some have worked out for our Sox and some have not. It is fair to assume that each team would be cautious about making another one but it could be on the table.

The reason that it could happen is the state of each team. The White Sox are trying to revive their season in order to make it into the playoffs. It has been a tough start but you never know what happens in the second half.

The Cubs are one of the worst teams in the league and are only going to get worse when they sell off all their assets. They have a lot of players at the top of their roster that contenders might want for the playoff chase.

If the Chicago Cubs and Chicago White Sox came together for another trade, it might look something like this:

The Chicago White Sox could try and land an old friend in a deal with the Cubs.

The Chicago White Sox once had David Robertson on their team. He was their closer in a time when they were trying to win but failed to be a very good team. He has since bounced around but is now having a really good year with the Chicago Cubs.

The Cubs are likely going to maximize his value and get something for him while they can. If it is a low-risk type of trade, the White Sox would be smart to do with it. Micker Adolfo (13th ranked prospect in the organization) and Jason Bilous (16th in the organization) would be a solid package for both sides in a deal like this.

Adolfo would probably be able to finally get his chance in Major League Baseball which would be amazing to see. Robertson certainly wouldn’t be the closer on the White Sox but he would be a great arm to add to the bullpen. It is something to think about.

(Photo by Chase Agnello-Dean/Getty Images)
(Photo by Chase Agnello-Dean/Getty Images) /

Ian Happ is someone that makes a lot of sense for the Chicago White Sox.

Of all the players that the Chicago Cubs are going to be selling, Ian Happ is probably the one that makes the most sense for the Chicago White Sox. There are a lot of extremely injury-prone outfielders on this team so Ian Happ would be perfect at this point.

He can play all three outfield positions if needed which would be extremely nice for the White Sox. It isn’t like this is some bench utility piece either. He is just getting back from the All-Star Game where he played for the National League All-Stars.

Happ would come to the White Sox and make an immediate impact. He would gel so nicely in this lineup as they try to get really hot offensively down the stretch. It is a no-brainer for Rick Hahn to call the Cubs and see what it would take for them to get Happ.

It isn’t like they are getting the farm from any team for Happ but they could get some really good players. Romy Gonzalez is someone that has made his Major League debut and has been really good in the minors this year. Adding Kade McClure along with him could get the deal done but even if it takes more, the White Sox should consider it.

(Photo by Maddie Malhotra/Boston Red Sox/Getty Images)
(Photo by Maddie Malhotra/Boston Red Sox/Getty Images) /

The Chicago White Sox could certainly use a big-time home run hitter right now.

The Chicago White Sox are one of two teams (the very lowly Detroit Tigers are the other) that have 70 percent or more of their hits as singles. They have a lot of very talented offensive players but they haven’t been hitting the ball over the fence enough.

They haven’t even been hitting enough extra-base hits so far this season. One player that might be able to help them with that is Patrick Wisdom of the Chicago Cubs. He isn’t good at a lot but he is really good at hitting the baseball for power.

If you put him on this team that is loaded with good contact hitters, they would certainly score a lot more runs. He would be going from a hitter-friendly park in Wrigley Field to another one in Guaranteed Rate Field as well which would help.

To get their hands on Wisdom, they would need to trade some good prospects but they wouldn’t need to break the bank to acquire a player over 30. Sean Burke and Jonathan Stiever are both pitchers that could be considered by the Cubs in a trade like this as they need more pitching prospects.

It isn’t a guarantee that they trade Wisdom as he is still under team control but it would be smart to sell him while he is a very good home run hitter. As soon as that part of his game starts to decline, he won’t be very valuable anymore. If the Cubs decide to move on from any of these guys, the White Sox should be involved.

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