MLB Expert projects what an Ian Happ contract extension would be for Cubs

Feb 27, 2023; Mesa, Arizona, USA;  Chicago Cubs left fielder Ian Happ (8) flies out in the first
Feb 27, 2023; Mesa, Arizona, USA; Chicago Cubs left fielder Ian Happ (8) flies out in the first / Matt Kartozian-USA TODAY Sports

Chicago Cubs all-star left fielder Ian Happ is entering his contract year as he will be a free agent next offseason and despite the Cubs saying at every stop this past offseason that they would like to sign Happ to an extension, it would appear that the Gold Glove outfielder will reach free agency next offseason.

Happ testing the free-agent market has always made the most sense for the player. With Manny Machado's recent contract extension with the San Diego Padres, Happ is in line to potentially be the best true position player on the market next winter. Shohei Ohtani is also scheduled to be a free agent but is in a class of his own.

The five-year, $75 million contract that free-agent outfielder Andrew Benintendi signed with the Chicago White Sox this offseason has always seemed to be the starting point for Happ in regard to his next contract.

However, that was not the comparison that Tim Britton had in his latest piece for The Athletic when he projected what a Happ extension may look like for the Cubs. Instead, Britton believes Nick Castellanos' five-year, $100 million contract with the Philadelphia Phillies may be the better example.

"Happ is a better corner outfielder than Castellanos, but it’s become tougher to squint to see him playing much time in center anymore. So let’s set Happ’s free-agent years a touch below Castellanos’ open-market deal to about $18 million per season. Add on the salary for this year, and you can get a six-year, $100 million deal."

Tim Britton via The Athletic

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Six years for $100MM seems like the most realistic extension for Happ and Cubs given the market inflation that Major League Baseball saw this past offseason. However, that market inflation is the very reason why Happ is likely to avoid signing an extension before reaching free agency. If Happ is able to put together another All-Star season in 2023, there is no question that his price will only go up, and that has always seemed to be the likely conclusion to his current contract status. The Cubs missed their window to sign Happ to a team-friendly extension and they will likely need to overpay next winter if they want to keep their left fielder.