Hutchinson started practicing football late in his life as a freshman in Torrey Pines High School. He was a two-year starter at outside linebacker that switched to quarterback as a senior, to take advantage of his mobility and arm strength. Even though he led a run oriented Wing T Offense, he recorded a 50% completion average, 1,441 passing yards and 8 touchdowns.
He was a rare two-sport standout, that also showed the talent to play professional baseball after his fastball was clocked at 94-mph. As a senior, he finished with an 11–0 record, a 1.20 earned-run average, 116 strikeouts and earned the Gatorade National Baseball Player-of-the-Year award. In school, he was a straight-A student and his college entrance exam score ranked among the top 10% in the country.
After choosing Stanford University over professional baseball, he was redshirted in football. The next year, he was named the starting quarterback over senior Tim Carey. He started slowly, but improved enough to lead his team to a 38–0 win over Michigan State and be named the MVP of the 1996 Sun Bowl.
In two seasons as a quarterback, he threw for 4,235 yards, 20 touchdowns and 22 interceptions in 23 starts. Scouts considered him to be a potential first-round draft choice in the NFL.
His development in football came without the benefit of spring practice, because he also was a starting pitcher for the Stanford Cardinal baseball team. He had a 7–2 record, with a 3.51 earned-run average as a freshman. The next year as the No. 2 pitcher, his 8–3 record and 110 strikeouts, helped the team reach the 1997 College World Series.
In 1998, he left school with two seasons of eligibility remaining, in order to play professional baseball with the St. Louis Cardinals.
Although Hutchinson had signed a letter of intent to attend Stanford University and was asking for a $1.5 million signing bonus' (at the time one of the biggest bonus ever by a draftee), he was still the 26th selection in the first round, after being drafted by the Atlanta Braves in the 1995 Major League Baseball Draft. He eventually decided to attend college, even after the Braves met most of his demands.
Hutchinson was selected in the second round (48th overall ) of the 1998 Major League Baseball Draft by the St. Louis Cardinals. He signed a four-year, $3.5 million contract ($2.4 million signing bonus and a $1.1 million four-year guaranteed contract) to forgo the NFL and play exclusively baseball. He began his minor league playing career with the Triple-A Memphis Redbirds.
Hutchinson pitched in the Major Leagues in three games, all in relief, for the St. Louis Cardinals during the 2001 season. He did not fare well, giving up 16 baserunners (nine hits, six walks, and one hit batsman) and 11 earned runs in just four total innings. His MLB career totals include an 0–0 record, two strikeouts (Ben Petrick and Denny Neagle), and an ERA of 24.75.
Struggling after a stint in minor league baseball, Hutchinson decided to focus on professional football and held an open workout in 2002 that was attended by three teams (Dallas, Chicago and Kansas City). Expecting that he could regain his football form, the Dallas Cowboys won a bidding war for his services, signing him as an undrafted free agent to a contract that included a $3.1 million bonus, three years guaranteed at $5 million and a no-baseball clause.
As a 25-year-old rookie, Hutchinson was named the starter after a struggling Quincy Carter lost to the Arizona Cardinals and engaged in a heated sideline argument with Dallas Cowboys owner and general manager Jerry Jones. Hutchinson's first start was the 17–14 loss to the Seattle Seahawks where Emmitt Smith broke the NFL all-time rushing record. His best game came against the Jacksonville Jaguars in a 21–19 victory, when he passed for 301 yards (most yards by a rookie since Troy Aikman in 1989) and 2 touchdowns. He finished with nine starts, completing 127 out of 250 attempts for 1,555 yards, 7 touchdowns passes, 8 interceptions and set an NFL rookie record by throwing 95 straight passes without an interception. A record broken by Carson Wentz at 134 then by Dak Prescott at 176 in 2016.
In 2003, with the arrival of new head coach Bill Parcells, all positions were opened to competition, and Hutchinson became involved in a highly publicized quarterback controversy, when he and Carter competed for a roster spot in the 2002 edition of Hard Knocks, an HBO series that covers the training camp of an NFL team. Carter eventually regained the starting role, bringing stability to the quarterback position and leading the team to a 10–6 record and a playoff appearance.
The Cowboys group of quarterbacks in the 2004 offseason had expanded with the trade for yet another former baseball player (Drew Henson) and the acquisition of Vinny Testaverde off waivers, who was later named the starter after Carter was released under unclear circumstances. Hutchinson was waived on July 27.
He left with a 2–7 record, 128 completions out of 252 attempts, 1,563 passing yards, 7 touchdown passes and 8 interceptions. He also became part of a succession of short-tenured quarterbacks following the retirement of Aikman, that included Carter, Randall Cunningham, Testaverde, Drew Bledsoe, Anthony Wright, Ryan Leaf, Henson and Clint Stoerner.
In 2004, the Cowboys allocated Hutchinson to the Rhein Fire of NFL Europe, so he could work on his accuracy and mechanics. He played inconsistently before suffering a right throwing shoulder injury toward the end of the season and would lose nearly a month rehabilitating it back to health.
On September 29, 2004, Hutchinson was signed as a free agent by the Chicago Bears, after Rex Grossman suffered a season-ending knee injury in the third game of the season, reuniting with quarterback coach Wade Wilson who also held that position with the Cowboys. He would become the fourth quarterback that year to start for the team, after Jonathan Quinn and Craig Krenzel were ineffective in their appearances.
Grossman was the projected starter entering the 2005 season, until suffering a broken ankle in preseason. Although Hutchinson was initially named the starter, he was eventually replaced in favor of rookie Kyle Orton, after he had poor preseason performances and the decision to sign Jeff Blake to be the backup. Following his demotion, he was released on August 31.
Hutchinson lives with his wife, and his son. His wife is the sister of baseball player Todd Walker. His father Lloyd was an outfielder in the Philadelphia Phillies' farm system and his brother Trevor was a pitcher in the Florida Marlins organization.