Cubs pitcher Ryan Rolison followed a long and winding road back to the big leagues

Rolison lived the ups and downs of a Major League Baseball player.

Cubs relief pitcher Ryan Rolison throws during a game against the Dodgers on Friday, April 24, 2026, in Los Angeles.

Cubs relief pitcher Ryan Rolison throws during a game against the Dodgers on Friday, April 24, 2026, in Los Angeles.

Ryan Sun/AP

SAN DIEGO — Fifty days in the life of a pro baseball player. Fasten your seat belt — and ask yourself after-ward how glamorous this life is.

Nov. 18: Left-hander Ryan Roli-son, a 2018 first-round draft pick of the Rockies who had one big-league win to his name after eight seasons in their organization, was removed from their 40-man roster. The move wasn’t unexpected. Rolison, 28, said he was informed a couple of days earlier.

Nov. 19: “Not 12 hours later, the Rockies called me back and said the Braves have traded for me,” Roli-son said. Officially, it went in the books as a cash transaction.

“Being from Tennessee,” he said, “a lot of people, my family and close friends, are Braves fans. Everybody’s fired up.”

Dec. 12: “Two weeks go by, and the Braves called and said, ‘We need to make a move.’ So I was on waivers again and got picked up the next day by the White Sox.”

Dec. 23, 2025: “I was on the roster a couple of weeks, and the White Sox call me on December 23rd and take me off the roster.” Merry Christmas, Ryan.

Dec. 24 to Jan. 6: Rolison was a man without a team. The new year began in limbo.

Jan. 7: Rolison and his fiancee, Lauren Hoselton, were on a plane to Chicago, to be married three days later at the University Club. Rolison had been awaiting a call to find out if he’d been claimed on waivers by another team. In the air, there was no cell phone service. They didn’t get the news until landing.

“I get claimed by the Cubs,” Rolison said. “It was a cool way to start off the weekend. My wife’s from Bloomington, and Chicago’s our favor-ite city.”

April 14: Rolison was promoted from Triple-A Iowa to the big leagues after right-hander reliever Ethan Roberts cut a finger on his pitching hand. He joined the Cubs in Philadelphia, pitching a mop-up inning in a 10-4 win over the Phillies. He then sat and waited for 10 days.

Last Friday: Lefty reliever Caleb Thielbar went on the 15-day injured list with a strained hamstring. The Cubs, on the road with a tired bullpen, trailed the Dodgers 4-0 after five. Manager Craig Counsell summoned Rolison to pitch the sixth. Then the seventh. Then the eighth.

The Cubs rallied. Alex Bregman hit a tying home run in the eighth. Dansby Swanson followed with a two-run homer in the ninth to win it. The winning pitcher: Rolison, for just his second big-league victory.

“Ryan Rolison, to me, is the story of the game,’’ a grateful Counsell said. “He hasn’t pitched [in 10 days] and gives an effort like that, three innings. I’m not sure he ever pitched three innings in a bigger game, and goes through the Dodger lineup. That was really impressive.”

The moment was a long time coming. Rolison had been shagging in the outfield one day in 2021 in the minors when a line drive he didn’t see struck him in his pitching hand, fracturing his middle finger and sidelining him for three months. He has had two shoulder surgeries, with rehab lasting 2 ½ years. He has had an appendectomy.

Then you have that incredible Friday night in front of 53,000 people at Dodger Stadium.

“You can easily get frustrated when you look at the guys you were drafted with and see their paths to the big leagues,” Rolison said. “For a long time, I think that just ate me up, being injured. But I finally came to terms with [the idea that] everyone’s got their own path.

“So it’s like trusting and staying patient. There’s a lot of times I could have laid down and quit . . . but I kept going. I kept sticking with the process, and it’s paid off.

“It’s special. I love it here.”

The Cubs can’t piece together an active roster with tin cans and string for too long. We’ll see whether winning a series in Milwaukee — to complete a 6-1 road trip — buoys them for a bit longer.
President Jed Hoyer and the front office moved to add healthy pitching in the wake of more injuries. With a trade and a waiver claim, the Cubs benefitted from the first attempts at finding fill-ins.
The Cubs took two of three from the division-leading Brewers, but they’re focus at the moment is on surviving a rash of pitching injuries more than it is on the rival that’s always standing in their way.

Gordon Edes

Gordon Edes

Chicago Sun-TimesSports contributor

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