Pittsburgh Pirates: Best Picks From Each of the First 10 Rounds

Round 8: Tim Wakefield

Tim Wakefield was an 8th round pick in the 1988 draft. Wakefield started his career as a light-hitting utility infielder before making his transition to the mound. Wakefield used his knuckleball to carve out a nineteen-year, 200-win career. However, the start of his career was a bit rocky, to say the least.

In Wakefield’s rookie season with the Pirates, the right-hander put up a 2.15 ERA, 3.27 FIP, and 1.21 WHIP through 92 innings during the 1992 season. He finished third in National League Rookie of the Year voting behind Eric Karros and Moises Alou. But after heavily struggling in 1993 and then missing 1994 due to injury, things weren’t looking so good for the right-hander.

The Boston Red Sox would then take a chance on him, where he would spend the next 19 years of his career and where he tossed 3006 of his 3226.1 innings. Overall, Wakefield put up a 4.41 ERA, 4.72 FIP, and 1.35 WHIP. Like most knuckleball pitchers, he didn’t have the best peripherals. Wakefield had just a 1.2 HR/9 rate, 15.5% strikeout rate, and 8.6% walk rate. But overall, he was an above-average run preventer, having a 105 ERA+.

Along with 200 career wins, Wakefield also finished third place in Cy Young voting in 1995 and won two World Series. The first was in 2004 and the second was in 2007. He made his first all-star game at 42-years-old in 2009, alongside Jonathan Papelbon, Kevin Youkilis, and Dustin Pedroia, who represented the Boston Red Sox during that year’s Mid-Summer Classic.