A Cubs-Pirates trade to send Jameson Taillon back where it all began

A month ago, it was obvious that the Chicago Cubs would be buyers at the trade deadline. They had an incredible pitching staff and were in firm control of a wild card spot. Since then, they've fallen apart and could be conservative sellers in the next couple of weeks.

A month ago, it was obvious that the Pittsburgh Pirates would be selling on all of their expiring contracts and continuing to rebuild through the farm system. Now, there's a chance that the Pirates will conservatively buy some controllable options at the deadline.

Today, these two teams have potentially switched roles. This is the exact reason that teams wait until the deadline to make most of their deals.

These two teams could come together to meet both needs in a deal to send Jameson Taillon back to Pittsburgh, where he was drafted 14 years ago.

A Pirates-Cubs trade to send Jameson Taillon back to Pittsburgh

Taillon spent the first four years of his big-league career in Pittsburgh before he ended up with the Yankees and eventually the Cubs. The righty signed a four-year, $68 million deal with Chicago before the 2023 season. He's still owed north of $40 million on his deal.

Projecting a deal for a player with a contract like Jameson Taillon's is especially complicated. There is usually a good idea about a player's value in a trade when they're on an expiring contract or they have arbitration years left. With this deal, it's hard to project because I can't give an accurate guess as to how much of his contract the Pirates would be willing to take on.

If the Pirates take on more of his contract, they would give up less prospect capital. If the Cubs eat the entire contract, the Pirates would have to give up more. This deal is assuming the Cubs will eat about half the contract, forcing the Pirates to pay the other half.

Hunter Barco and Patrick Reilly are two of the better performing prospects in the Pirates system this year. They are both incredibly talented and have shown successful ways of attacking hitters, Reilly doing so with an explosive fastball and Barco having a bit more pitchability in his arsenal. Both project to continue up the minor leagues with success.

Delgado is quite the prospect in his own regard. He's a projectable, 20-year-old switch hitting infielder that has shown the ability to hit in the lower levels of the minor leagues. He would be a valuable prospect in any system.

The Pirates need one more starter to finish out their rotation for the next few years. With the way that Taillon has thrown this year, bringing him home to Pittsburgh as they try to put together a lineup to hit for him, would be a Hollywood story.