I am going to start this off by saying this is strictly a hypothetical scenario as I don't think the White Sox will ever want to trade Sale. I had a joking back-and-forth with noted Pirates blogger Brian McElhinny on Twitter today when he accidentally typed 'sale' instead of 'sell' and I jokingly asked if he was hinting at a Chris Sale trade.
That got me to wondering if a Chris Sale trade would even make sense for the Pirates to do. Assuming that the White Sox would be crazy enough to deal Chris Sale let's take a look at what the Pirates would have to give up in order to get him and how he would fit on the Pirates' roster
The White Sox have a fairly weak farm system, with only two prospects on MLB.com's top 100 list. They have needs in the outfield, at catcher and for pitching. The Sox would most likely want three of the Pirate's top five prospects. I think the White Sox would want number one Pirates' prospect Tyler Glasnow, number two Austin Meadows and number five Reese McGuire. Glasnow is ranked number 10 on the top 100 list and the number two ranked right handed pitching prospect. Glasnow would immediately become the White Sox number one prospect and will most likely make his major league debut in 2016. Meadows in the Pirates' top ranked position player and in the number 20 overall and number four outfield prospect. Meadows would become the White Sox top position prospect. Finally, McGuire is the fourth ranked catcher prospect and would be the White Sox fifth best prospect behind Glasnow, Meadows, pitcher Carson Fulmer and shortstop Tim Anderson.
In recent years Pittsburgh has shown a reluctance to trade away prospects for big league talent, but I think their farm system could survive losing these three prospects. The Pirates have more top pitching prospects in Jameson Taillon (#4 Pirates, #54 overall) and Nick Kingham (#12 Pirates). They have outfield prospects behind Meadows in Harold Ramirez (#6 Pirates) and Willy Garcia (#13 Pirates). And they have Elias Diaz, the number 6 ranked catcher prospect and number eight ranked Pirates Prospect to fill in for McGuire.
Some might see this as giving up too much for one player, but the Pirates would still get to keep firstbase prospect Josh Bell, shortstop Alen Hanson and the previously mentioned Taillon to keep the farm system strong.
On to how Sale would fit with the Pirates' roster, let's start with payroll. Sale's current contract has him signed through the 2019 season with club options in 2018-19. Sale stands to make $9.15, $12, $12.5 and $15 million during those years. That makes him the third highest paid player in 2016 and 2017, the second highest paid in 2018 and the highest paid currently under contract in 2019. Sale's contract would also push the Pirates' up to about $95 million, which would move them above the Oakland A's with the 23rd highest payroll. The team would also most likely receive a compensation draft pick in 2020 if they don;t resign Sale and he signs somewhere else, which he probably would.
Sale would join Gerrit Cole and Francisco Liriano at the top of the Pirates' rotation to make a deadly trio. Cole (19 wins, 2.60 ERA, 208 innings, 202 strikeouts), Liriano (12 wins, 3.38 ERA, 186.2 innings, 205 strikeouts) and Sale (13 wins, 3.41 ERA 208.2 innings, 274 strikeouts) would make arguably the best trio of starting pitchers in the league, and realistically carry the team to possibly a division title. The downside is that would put four lefties in the Pirates' starting rotation with Liriano, Sale, John Niese and Jeff Locke.
In conclusion Sale would be an outstanding addition to a Pirates' starting rotation that is full of question marks. However, the Pirates' would have to give up three of their best prospects and tie up a large portion of their payroll just for one player. The White Sox would also have to basically give up on winning in 2016 and be willing to bet on a couple of prospects for the future. I don't think this trade could ever happen and I don't even think it should. The Pirates would have to give up too much in terms of prospects and payroll for only four years of Chris Sale.
