While Marc-Edouard Vlasic kept the number 44 under lock and key with the San Jose Sharks for nearly two decades, shortly after he departed the organization, a new face took over.

The Sharks acquired Kiefer Sherwood from the Vancouver Canuck on January 19, 2026 for a pair of second round draft picks and defenseman Cole Clayton. Less than two month later, the Sharks signed the veteran winger to a five-year contract with an average annual value of $5.75 million to retain his services for the foreseeable future. With that being said, things weren't always this smooth for Sherwood, as he had to overcome massive odds to ever be seen as a legitimate NHL prospect.

As an undrafted player, Sherwood's NHL journey began alongside his younger brother Kole when the duo were invited to attend development camp with their hometown team, the Columbus Blue Jackets in 2015.

After showing off what they could do at development camp, the Blue Jackets offered Kole Sherwood an entry-level contract while letting Kiefer return to Miami University for the 2015-16 season.

Kiefer would go on to earn an entry-level contract of his own toward the tail end of the 2018-19 season with the Anaheim Ducks, but after two seasons split between the NHL and their American Hockey League affiliate, the San Diego Gulls, the Ducks opted not to extend a qualifying offer to Sherwood, allowing him to become an unrestricted free agent.

Sherwood then joined the Colorado Avalanche for the 2020-21 season, where he again found himself stuck between the NHL and AHL. The same was true for the 2021-22 campaign, but he spent the majority of that season with the Colorado Eagles.

After another tweener season during the 2022-23 season, this time with the Nashville Predators, Sherwood finally got his first opportunity to stick in the NHL on a full-time basis during the 2023-24 season. In 68 games, he scored 10 goals and added 17 assists, attracting the interest of the Vancouver Canucks.

During his first season north of the border, Sherwood scored a career-high 19 goals and 40 points in 78 games. He then scored 17 goals and 23 points with the Canucks to start the 2025-26 season before he was traded to San Jose.

Compared to most 31-year-old NHLers, Sherwood has less of a proven track record as he prepares for his first full season in the Bay Area. With that being said, sometimes all late bloomers need is a true opportunity, and that appears to have been the case with Kiefer Sherwood.

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