The Chicago Cubs are struggling and most definitely not looking like a team likely to make a deep playoff run.
These things come in waves, though. The baseball season is long and there are always ebbs and flows in momentum. However, the team;s recent run of losing four of their last five is coming at the absolute worst moment as the red-hot Milwaukee Brewers have overtaken them for first place in the NL Central Division.
Despite everything good and borderline magical the Cubs have going for them, their weaknesses and liabilities are screaming to be heard as the season advances.
By all accounts, those screaming foibles are currently being addressed by Cubs president of baseball operations Jed Hoyer via the trade market, prior to the July 31 trade deadline.
Multiple trade deadline pickups by the Chicago Cubs?

ESPN MLB insider Jesse Rogers, in a Friday appearance on the Waddle and Silvy Show, says that Hoyer has multiple irons in the fire when it comes to deadline deals to fill roster holes. He also asserts that the Cubs may end up with a haul of acquisitions beyond what many have anticipated.
Per Rogers:
“What I know is that Jed is trying hard…I think it’s all going to happen, or most of it, for the Cubs in the last 72 hours…I think they’re looking for a backup outfielder, especially in center, maybe that third baseman and a pitcher or two. So, I think there are still three or four additions, whether one of them goes to the minors or not remains to be seen, but I think all of that is going to happen late…I think he wants to try to get a pitcher before the week starts, it’s just been really difficult sledding so far. Tons of competition…Pitching is a priority, but [Eugenio] Suarez is definitely in the mix.”
Three or four pickups by the deadline would be tremendous, considering the team’s clearly established needs.
Rotation and bullpen needs

First and foremost among the Cubs’ needs, as Rogers affirmed, is pitching.
A starting pitcher is a must. Actually, two starting pitchers would be ideal as the team would do well to add a high-end rotation piece as well as a back-of-rotation inning eater. Rumored names have popped up all over the place, but a team-controlled Edward Cabrera from the Miami Marlins and the rental ground ball specialist Adrian Houser from the White Sox (who befuddled the Cubs on Friday) would be outstanding acquisitions.
Over the last month or so, the relief corps has also become a Cubs pitching concern. The formerly overachieving bullpen, which once ranked among the very best, has come crashing hard down to earth. Since July 1, per Marquee Sports Network, the Cubs pen has ranked next to last in all of baseball with a 6.31 ERA. As a result, relief help also has to be put on Hoyer’s deadline shopping list.
The healthy, productive return of Jameson Taillon and Javier Assad should help the team’s pitching overall, but that help would come a little bit down the road. The Cubs need help right now and they need sure things (or as close to sure things as possible in baseball).
Outfield and third base

Outfield help is also a clear need as the season pushes on and the current three starters– Ian Happ, Pete Crow-Armstrong, and Kyle Tucker– start to show signs of wear and tear. A dedicated fourth outfielder should’ve been on the roster from day one.
At third base, there was persistent talk about Matt Shaw’s failures at the plate and the need for a replacement. Since coming back from the All-Star break, however, the rookie is batting .500 with 3 home runs and 6 RBIs. His defensive play has also been stellar. Unless they can get Eugenio Suarez from the Arizona Diamondbacks on a sweetheart of a deal, the Cubs may be fine with letting Shaw stay put and maybe just adding a third base-capable bench upgrade.
Minnesota Twins switch-hitter Willi Castro, who can play all three outfield positions, as well as third base, second base, and shortstop, would be an ideal jack of all trades to cover all of the Cubs’ remaining position player needs.
Things should get interesting as the trade deadline approaches. The Cubs’ postseason viability may depend on the moves made.
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