The Cubs face an often overlooked extra obstacle in acquiring Paul Skenes‌

Because the Pittsburgh Pirates are both a ridiculous organization that never really tries to win and because they have one of the best pitchers in baseball, most people around the sport, including those associated with the Chicago Cubs, believe that sooner or later, the budding superstar pitcher will be traded. If and when he does, North Sider fans would love to see him call Wrigley home. Unfortunately, while it's highly unlikely Skenes gets traded any time soon, it's even more unlikely that he'll ever get traded from the Pirates to the Cubs.

The Pittsburgh front office and ownership are already deeply unpopular. That tends to happen when a franchise constantly trades away its best players, rarely, if ever, competes for a playoff spot, let alone a pennant, and, these days, doesn't even have that many good players despite acquiring every other team's prospects year in and year out.

If the Pirates think the chants from their own fanbase to "sell the team" are loud now, imagine the volume if Paul Skenes was somehow dealt to the Chicago Cubs in 2025, 2026, or even 2035.

Paul Skenes probably isn't going to another NL Central team in a trade

While baseball is different from what it was a few decades ago, when an inter-divisional trade was simply unheard of they're still rare, especially when such a trade would benefit one of the divisional foes as much as acquiring Paul Skenes for as long as it would considering how young the hurler is.

Even if the Cubs could come up with what will be an incredible asking price, even if they were willing to part with some variations of a package that includes top prospects like Matt Shaw, Cade Horton, Owen Caissie, Kevin Alcantara, and Moises Ballesteros, the Pirates would look almost anywhere else first.

It's not outrageous to think that the Pirates would turn a deal down even if the Chicago Cubs were willing to part with several of their best young players with an offer that any other team would jump at. That's the extra obstacle the Wrigley Field denizens face that most other clubs don't need to worry about. But there's always a chance they could outbid everyone once Skenes becomes a free agent.