Craig resisted jumping to major junior hockey in order to get a chance to earn an all expense paid scholarship from a major US hockey college. After two strong seasons with the BCJHL Abbortsford Flyers, the scholarship offers came pouring in for the 1982-83 season. Redmond finally decided to head to the University of Denver of the WCHA.
Redmond had an incredible rookie season in Denver, turning many heads - especially those of National Hockey League scouts. He had a 16 goals, 38 assists and 54 points in 34 collegiate showdowns. He showed great offensive ability, suggesting to some that he could become one of the elite offensive rearguards down the road.
After the Kings drafted Redmond so high, he decided to put school on the backburner and give a professional hockey career a full shot. He dropped out of school in order to skate with Dave King's Canadian national team. Not only was it a great opportunity because it was an Olympic year, but it was a great chance to improve his game. King was notorious for his defensive hockey, something Redmond was not known for. Redmond and the Kings felt it would best if he apprenticed under King's watchful eye for the year.
Redmond had a decent year and made the Olympic team. He scored twice in 7 games in Sarajevo, but the Canadians failed to medal.
Redmond made the jump to the NHL in 1984-85. He had a nice rookie season, scoring 6 goals and 39 points. He was by no means dominant but for a NHL rookie defenseman he was a serviceable player, particularly on a bad Kings team.
However Redmond's career would turn downwards in his sophomore season in 1985-86. Craig had a real tough year that year, collecting just 24 points but also struggling defensively, finishing with a bad -34. The LA Kings failed to make the playoffs, and Craig used the opportunity to return to the international game, playing 10 games for Canada in the World Championships.
1986-87 was even worse for Craig. Because of a serious knee injury, Craig only appeared in 16 contests. He looked better in those games than he had in the previous year, scoring 1 goal and 8 points and improving his +/- to -1. However the knee injury took a lot out of Redmond.
1987-88 was a weird year for Craig. Obviously relations between Craig and the Kings had soured. Craig had recovered from his knee injury and started his comeback. But after just two games, the Kings wanted to demote Craig to the minor leagues, which was a move Redmond was not prepared to do. The Monarchs were forced to suspend Redmond when he refused to report to New Haven. Redmond instead demanded a trade.
The trade never came all season long. Teams were weary of Craig's knee, as well as his on-ice shortcomings. He had failed to establish himself as an offensive presence at the elite level. His defensive play was poor, and like many young defensemen, he was prone to making costly errors in his own zone. He also lacked any physical game, and had trouble with NHL power forwards. Add that to the fact that he missed basically two years of development due to the knee injury and his subsequent hold out, it was a very long 1987-88 season for Craig.
Craig's trade came in the summer of 1988. He was traded from Los Angeles to Edmonton just two days after the two teams got together to make the biggest trade in NHL history - sending the great Wayne Gretzky to Hollywood. Essentially Redmond was part of the package that came to Edmonton in exchange for Gretzky, even though it took a couple of days later for the two to come to terms. The Oilers agreed to send John Miner, a minor league defensemen, to LA on August 10 1988.
Redmond did play in Edmonton for 21 games in the 1988-89 season, but it was a round about arrival to the Alberta capital. After training camp, the Oilers had to expose Redmond in the pre-season waiver draft, and the New York Rangers quickly grabbed the smooth skater. He was immediately sent to the minor leagues, and he did report. He spent the month of October playing 10 games back in Denver, with the IHL Rangers, and picked up 13 points, all assists.
After the quick start, the Rangers recalled Redmond at the end of the month as an emergency injury replacement, except he never did get into a game. Once the injury situation eased up the Rangers had to put Redmond on waivers again in order for him to go back to Denver. The Oilers took the opportunity to grab him back.
The Oilers, looking for a true offensive defenseman ever since the departure of Paul Coffey, gave Redmond a good look. In 21 games Redmond was given some good powerplay time, scoring 3 times and adding 10 points. However he was, as always, an adventure at even strength as his -10 attests. The Oilers demoted Redmond to their farm team in Cape Breton for the second half of the year, where Craig played well.
Frustrated with the way his career had been going and the way NHL teams had dismissed him, Craig walked away from the game before the 1989-90 season started. Perhaps looking for some closure, Craig made a comeback 5 years later, spending the 1995-96 season split between the AHL Cape Breton Oilers and the IHL Atlanta Knights.
All said, Craig was a first round draft bust who played in 191 games, scoring 16 goals, 68 assists and 84 points. He got into only 3 playoff games, scoring 1 goal.