Investing big money in free agent pitchers can be a risky proposition. Some guys break down as they get older, others seemingly fall apart the moment the ink on their contract is dry.

But some arms are worth the money, and Gerrit Cole is Exhibit A for how a big deal can pay off.

The New York Yankees’ ace won his first career Cy Young Award on Wednesday, earning the American League honor unanimously to beat out Minnesota’s Sonny Gray and Toronto’s Kevin Gausman. It’s the latest highlight for the big right-hander, who has been everything the Yankees could have hoped for since signing a nine-year, $324 million deal ahead of the 2020 season — the largest contract for a pitcher in MLB history.

Other than a brief two-week stretch in 2021 when he was sidelined with COVID-19, Cole has made every start for New York through his first four seasons, posting a 3.08 ERA with 816 strikeouts over 664 innings. His 17.8 wins above replacement is second only to Philadelphia’s Zack Wheeler (19.6) over that span, and this season he captured his first Cy Young Award after leading the league in innings (209), ERA (2.63), pitcher WAR (7.4) and WHIP (0.981) while ranking third in strikeouts (222).

Yes, Cole did last only two innings against the Red Sox in the 2021 Wild Card Game, but outside of that he’s also come through in the playoffs, posting a 3.49 ERA in seven postseason starts with New York. Obviously this year the Yankees had a lot of problems, but Cole wasn’t one of them.

Hopefully the Red Sox have taken note.

This offseason the Red Sox have indicated they plan to improve their starting rotation, and while there are plenty of enticing arms available, they aren’t going to come cheap. The 25-year-old Japanese superstar Yoshinobu Yamamoto will likely command a deal well north of $200 million, and any other established MLB starter — including National League Cy Young winner Blake Snell — will cost a lot of either money or prospect capital, possibly both.

MLB notes: The Red Sox need starting pitching, and there will be plenty available this offseason

Making that kind of investment in a pitcher hasn’t always worked out for Boston. Chris Sale’s five-year, $145 million extension has been a bust, and David Price barely made it halfway through his seven-year, $217 million deal, the largest in club history for a pitcher. You don’t have to look hard for other recent examples of big deals that have gone sideways.

But that risk comes with the potential for a big reward, and if the Red Sox hope to turn things around they’ll have to take the plunge, extend themselves and bring in an arm strong enough to carry the load.