The Detroit Tigers have a few success stories to their name when it comes to first-round draft picks: Kirk Gibson and Justin Verlander immediately spring to mind, one as a member of the most recent World Series team in 1984 and the other as a lock for the Hall of Fame. More recently, Spencer Torkelson and Riley Greene were back-to-back first-rounders in 2019 and 2020 and have already displayed some flashes of brilliance in their young careers.
You can look all over the internet for debates about which draft class is the absolute best. 2009 (featuring Mike Trout, Paul Goldschmidt, and Nolan Arenado among many others) and 2011 (Francisco Lindor, Gerrit Cole, and George Springer) rank among them as modern examples, but if we look a little further back to 2006, there are a couple of guaranteed Hall of Famers who went in the first round.
That year, the Tigers had sixth pick and the Dodgers had the seventh. The Tigers chose Andrew Miller, a bust with Detroit who went on to be a two-time All-Star and ALCS MVP with Cleveland. The Dodgers chose Clayton Kershaw, who needs no introduction.
Andy McCullough of The Athletic, who wrote a biography of Kershaw (entitled The Last of His Kind) releasing on May 7, released an excerpt in the wake of Kershaw's re-signing with the Dodgers (subscription required). In it, he details the nerves surrounding the Dodgers seventh-place pick and the threat the Tigers posed to them as they equivocated between Miller and Kershaw.
New book details how Detroit Tigers could've chosen Clayton Kershaw in the 2006 draft
McCullough quotes then-Tigers GM Dave Dombrowski: "If Andrew Miller wouldn’t have been there, Clayton Kershaw wouldn’t have been a Dodger," which makes everything just that much more tragic. By the end of his career, Miller was no slouch, but he sort of was with the Tigers. He only pitched for Detroit for a season and some change before being traded to the Marlins. That trade, of course, netted the Tigers their own future Hall of Famer in Miguel Cabrera, so this is far from a total loss.
Kershaw didn't have the same growing pains as Miller; to this day, his worst ERA year was his rookie season, and he just hasn't slowed down from there. The entire course of Tigers history could've been changed with Kershaw in the Old English D (a 2012 rotation that featured Kershaw, Verlander, Max Scherzer, and Rick Porcello?), but alas. Kershaw is headed back to the Dodgers for his 17th season and we can only wonder what could've been.