The first time Rich Hill signed a contract with the Red Sox, Theo Epstein led the front office.

That was in June 2010. He became a free agent in November 2010, and re-signed with Boston a month later. The same thing happened the following December. He became a free agent on the 12th, and re-signed on the 13th.

Between February and March 2014, the Sox signed him twice. They signed him again in August 2014. And in December 2021. And finally, 10 days ago, they signed him for what Baseball-Reference lists as the 10th time (minor- and Major-League contracts).

Hill was Red Sox teammates with Craig Breslow and Andrew Bailey on the 2011 Red Sox. Breslow is now the fifth head of Red Sox baseball operations to sign Hill to a contract, and when the Sox called Hill up from Triple-A on Tuesday, Bailey became his pitching coach.

After 19 seasons, Hill opted to remain unsigned heading into 2024. He spent the summer with his family and coached his son’s Little League team. But he’d always planned on pitching later in the season, and made sure he was ready for that opportunity.

“Kind of a great summer,” Hill said as he stood in the Red Sox clubhouse on Tuesday afternoon. “Putting in the work and time and effort throughout the entire summer has obviously come to this point where we’re at today.”

“He was very diligent the last few months about his craft,” said manager Alex Cora. “No doubt about him, that physically, he’s going to be okay.”

Hill last pitched in a Major League game for the San Diego Padres last October 1, but even one two-inning appearance in Triple-A Worcester, the veteran southpaw felt confident he could contribute in Boston.

“I think the way the ball is coming out of my hand,” he said. “I know it was a couple of innings in Worcester, but I think the way the hitters were reacting and the way the ball was breaking, the life on the fastball, the execution… everything was checking a lot of boxes.”

Asked how they envision Hill’s role, Cora said, “He’s willing to do anything. We know he can get lefties out… We’ll use him the right way.”

“Go out there and compete and make pitches and get outs and play with a relentless attitude,” Hill said. “In any role at any time.”

Playing close to home factored into Hill’s decision to re-sign with the Red Sox, as did the fact that the team is in the Wild Card hunt. Now in his 20th MLB season, the Milton, Mass. native has never won a World Series. He became a free agent after the 2012 Red Sox season, thereby missing the ’13 championship, then faced them in the Fall Classic as a member of the Los Angeles Dodgers in 2018. The Dodgers won the 2020 World Series, the season after he signed with the Minnesota Twins.

Hill was in Cooperstown, New York with his Little Leaguers when he re-signed with the Red Sox.

“Keep your fingers on top, throw the ball downhill, work over the rubber, take a deep breath,” he joked, when asked if the kids gave him any advice.

A summer in Little League rejuvenated the lefty, who will turn 45 in March.

“Being around the kids this summer and them, just the love that they have for the game of baseball,” Hill said. “I wouldn’t be doing this if I didn’t love, love to play the game. And I also wouldn’t be doing it if I didn’t think that I had ability to continue to go out there and compete, and not only compete, but also contribute in a positive way to a Major League clubhouse.

“Watching those kids play, and day in and day out the way they would go about their business, although it might have been at a Little League level, it’s still the same joy and the passion, the ups and the downs that we experience here in the big leagues.”