Column: It’s Ian Happ’s year to deal with free-agency questions. Will the Chicago Cubs reach an extension this time?

Anthony Rizzo, Kris Bryant and Javier Báez spent the first half of the 2021 season answering questions about their uncertain futures as Chicago Cubs.

Last year Willson Contreras was the man of the hour, handling questions over and over again about his impending free agency and the possibility of being traded.

Now it’s Ian Happ’s turn.

The switch-hitting Cubs left fielder enters his walk year off a career-best season in which he made his first All-Star team and won his first Gold Glove. He is popular with fans — albeit not on the same scale as Rizzo, Bryant, Báez and Contreras — and has a good relationship with Cubs Chairman Tom Ricketts.

It would seem likely the Cubs would be interested in signing Happ to a long-term deal, but the same could be said for the other four players who are currently playing elsewhere. And no prominent Cub has signed an extension since Kyle Hendricks in 2019.

Ricketts and Happ had a conversation at Cubs camp Monday, but whether that suggests an extension is on the way is anyone’s guess.

Ricketts said Monday he would leave those kinds of decisions up to President Jed Hoyer.

“Obviously we have a couple guys we’d love to extend, but if it doesn’t work out, that’s OK too,” Ricketts said. “I appreciate that they would rather test the market. It’s up to Jed, but it’d be great. Not only some of the guys that we’d consider extending, we know them as players, but also as people and the kind of people you want to be around and want in the clubhouse.”

Who are those two guys?

“Ask Jed,” he said with a grin.

Happ definitely was one, and Nico Hoerner is likely the other. Hoyer wouldn’t talk about extension discussions, but now would be the time to get something done.

“My preference is not to get into (talks) toward the end of spring training and get to a place where I feel like it’s affecting the preparation and mentality for the season,” Hoyer said. “I do think that has happened, and I’ve seen it happen before. That’s something we’re aware of. We’ve talked to both camps about that. But the conversations are good.”

The fact the Cubs expect to contend changes the dynamics a bit after they entered 2021 and ‘22 with little hope of winning the division. Contreras and Happ were rumored to be trade bait last July and memorably hugged in the dugout after the last game at Wrigley Field before the trade deadline. Happ was emotional about a nice gesture from the left-field bleacher bums, who autographed a ball for him in case it was his final home game as a Cub.

When neither one wound up traded, Happ jokingly blamed the media.

“All those stories and the cameras the last couple days at Wrigley, it’s all on you guys,” he said.

Asked this week at camp if he’s ready to go through the same kind of media focus this summer, Happ went into prevent-defense mode.

“Long way away,” he said. “We’ll figure it out when we get there.”

But after watching what Rizzo, Bryant, Báez and Contreras went through, he has to be ready for the possibility of being dealt at the deadline if he’s not signed by then.

“Every experience prepares you,” he said. “It prepared you for last year by watching guys that went through it in ‘21. It’s part of the game and you don’t really know how you are going to feel until you go through something like that.

“But once you’ve been through it a couple times, you have an understanding for it.”

Would he ever talk directly to Ricketts, or does he prefer to leave everything to his agent?

“That’s something that, uh … however they want to deal with it,” he said.

Happ clearly didn’t want to discuss his future at the start of spring training, and who could blame him? He has made it clear he wants to stay, just as Rizzo, Bryant, Báez and Contreras did.

But Happ also knows that not talking about it won’t end speculation on whether he’ll re-sign or arguments over how much he would command as a free agent.

According to FanGraphs, Happ ranked third among left fielders last year with a 3.5 WAR, behind the Houston Astros’ Yordan Álvarez (6.6) and the Cleveland Guardians’ Steven Kwan (4.4). Just behind him was the New York Yankees’ Andrew Benintendi (2.8), who signed a five-year, $75 million deal with the White Sox.

Happ and Benintendi are both 28 and have had similar career paths. The Boston Red Sox selected Benintendi with the No. 7 pick in the 2015 draft, and the Cubs chose Happ two picks later. Happ has 104 career home runs and a .798 OPS, while Benintendi has 73 homers and a .782 OPS. Happ is a better defensive player, ranking sixth among all outfielders last season with 14 defensive runs saved.

But Benintendi signed the biggest free-agent deal in White Sox history, while Happ won’t come close to Jason Heyward’s Cubs-record eight-year, $184 million contract.

If he has a season comparable to 2022, Happ should expect to exceed Benintendi’s deal. If he has a drop-off, it’s anyone’s guess.

Either way, the clock is ticking.

And Wrigley’s left-field bleacher bums might want to practice their autographs, just in case.