Rick Porcello
This one might raise a few eyebrows given those who are now known to have been left off of this list, but hear me out. Rick Porcello came over in the Yoenis Cespedes trade in 2015 (in effect, Jon Lester begat Rick Porcello by way of Cespedes). The Red Sox immediately signed him to a four-year extension before he’d even thrown a single pitch and while he’d been good in Detroit, we had no idea why they jumped the gun.
From 2015 to 2019, Porcello was the most reliable and durable pitcher the Red Sox had, routinely making 28 or more starts in each of those seasons. He seemed to fall prey to the “even year curse” where he pitched well in even-numbered years and poorly in odd-numbered years. Luckily, two of those even-numbered years coincided with great success.
His 2016 season (22-4, 3.15 ERA, 189 K, 1.009 WHIP) won him the American League Cy Young Award. In 2018, he went 17-7 with a 4.28 ERA and 190 strikeouts in helping the team win the World Series. His one glaring flaw was his propensity to give up home runs and he even led the league in homers given up in 2017 with 38 of them.
For his entire Red Sox career, Porcello went 73-55 with a 4.50 ERA, and 852 strikeouts in 964 innings. While Chris Sale and David Price may have been better pure pitchers, Porcello was durable, a bulldog on the mound, and delivered in plenty of big spots himself. He deserves to be on this list.