Jeff Chiu/Associated Press

Madison Bumgarner is reportedly looking to get paid in a big way this winter.

According to Bob Nightengale of USA Today, "teams are being told" that the veteran starting pitcher is looking for a five-year deal totaling $100 million or more in free agency.

Whether Bumgarner receives that level of compensation—or should get paid in such a major way—is a fascinating conversation. 

One one hand, Bumgarner is a postseason legend who has a career 8-3 record in October baseball with a 2.11 ERA, 0.90 WHIP and 87 strikeouts in 102.1 innings (14 starts). He was a key factor in the Giants winning three titles between 2010-14. 

He also had a solid 2019 season, finishing 9-9 with a 3.90 ERA, 1.13 WHIP and 203 strikeouts in 207.2 innings. 

But there are risks to committing five years to Bumgarner.

He's already 30, for one, and will turn 31 on Aug. 1. He only made 38 starts between the 2017-18 seasons due to injuries. His 2.5 WAR was 31st among National League pitchers this past season, trailing fellow free agent Hyun-Jin Ryu (5.1) and ZacK Wheeler (3.5), who recently signed a five-year, $118 million deal with the Philadelphia Phillies.

Ryu has had his own durability issues, but he may also come as a cheaper option for teams seeking pitchers in the tier below the top names (Gerrit Cole, Stephen Strasburg). And many teams may choose to bypass the bidding for the top starting pitchers altogether, given the level of money that is expected to be handed out:

That could make the market for players like Bumgarner more vibrant, especially after Wheeler's lucrative deal. Bumgarner may come with obvious risks—and some teams may drop out altogether if he insists on five years—but it isn't out of the question that a team desperate for pitching could splash the cash and years to acquire his services in this market.