Stottlemyre was originally drafted by the New York Yankees in the 5th round of the 1983 amateur draft, but did not sign. He attended Yakima Valley Community College, and in 1985 he played collegiate summer baseball with the Harwich Mariners of the Cape Cod Baseball League. He was drafted by the St. Louis Cardinals in the 1st round (1st pick) of the 1985 amateur draft (January Secondary), but he did not sign again.

The Toronto Blue Jays selected him out of UNLV as the third overall pick in the 1985 MLB draft and he signed with them on August 12, 1985. He spent seven seasons with the Blue Jays, helping them win the 1992 & 1993 World Series. His best season came in 1991, when he recorded 15 wins, pitched 219 innings with an E.R.A. of 3.78.

Stottlemyre is married with five children. He is the son of Mel Stottlemyre, former New York Yankees pitcher. His brother Mel Stottlemyre Jr. also pitched in the major leagues for the Kansas City Royals in 1990, and is currently the pitching coach for the Miami Marlins.

On February 20, 1994, Stottlemyre and Blue Jays teammate Dave Stewart were both arrested in Dunedin, Florida, for battery on a law enforcement officer and resisting arrest after an argument arose between Stewart, who was accompanied by Stottlemyre, at a night club, reportedly over Stewart’s refusal to pay a $3 cover fee.

Stottlemyre signed with the Oakland Athletics for the 1995 season. He was traded to the Cardinals prior to the 1996 season where he put up respectable numbers for nearly three seasons. On July 31, 1998 (trade deadline day) the Cardinals traded him along with Royce Clayton to the Texas Rangers in exchange for Darren Oliver, Fernando Tatis and a player to be named later (Mark Little). Stottlemyre could not replicate the success he previously had and retired as a member of the Arizona Diamondbacks in 2002.

Stottlemyre became interested in the stock market soon after receiving his signing bonus with the Blue Jays. He hired long-time family friend Frank Aiello to manage his portfolio, where Aiello purchased shares in Pepsi prior to a 3:1 stock split. After he was placed on the disabled list for the Arizona Diamondbacks in 2000, Stottlemyre began to get “really serious about trading”.

After retiring from baseball in 2002, Stottlemyre became a stock market analyst for Merrill Lynch. Realizing that he was a better trader than investor, he began day trading and cites the mentorship of Joe Donohue and Brian Shannon with his success. Later, he followed his dream of founding a hedge fund.

As of 2010, Stottlemyre is a member of ACN Inc., operating a network within the multilevel marketing company selling telecommunications, energy, banking, and other services. He is now a Platinum Regional Vice President of the company.