Driving around Nantucket with a friend last week, Kyle Shepard received a call from Matt Sherman, a regional scout for the Chicago Cubs, covering New England and Eastern Canada.
He offered Shepard a free agent contract to play baseball professionally with one of the oldest organizations in the game.
“When I saw who was calling I kind of had an idea what it might be about,” said Shepard, a 21-year-old left-handed pitcher from Boxford who is coming off a nice bounceback season as a senior at Stonehill.
“I was pretty excited. Matt told me they were really interested in signing me, and we got things done pretty quickly.”
“It's always been a goal of mine to be a professional baseball player.”
The previous week, the 6-foot-1 Shepard stood by his computer watching names flash past him on the third day of the Major League Baseball entry draft. After being in contact with scouts from the Braves, Orioles, and Cubs organizations, he felt that there was a good chance that he would be drafted.
Far from being dismayed, Shepard went about his business, where most others in his shoes might not.
“I told my dad beforehand that I'm not going to get over-excited about things,” said the level-headed Shepard. “I was a little disappointed that I wasn't picked, but I was over it quickly and knew I would just return next year and have a better chance.”
He was content because he already had a plan in place: Stay sharp over the summer while hurling for the North Shore Navigators of the Futures Collegiate Baseball League, return to Stonehill, and improve his draft stock.
At Masconomet Regional, Shepard excelled both on the hill and as an outfielder.
He went 7-1 as a senior and earned Cape Ann League all-star honors after helping lead the Chieftains to an 18-6 record and a Division 1 North championship.
Then he joined his older brother, Brendan — another solid two-way player — at Stonehill.
In his freshman season, Shepard made only three appearances, going 1-0 with a save and six strikeouts in four innings of work.
Then he felt a pop in his arm, a torn ligament in his left elbow, precipitating Tommy John surgery and a red-shirt sophomore season.
Upon his return for his junior year, and wanting to ease his arm back, Shepard only played in the field, a season in which head coach Patrick Boen called him “arguably one of the best outfielders in the Northeast-10 [Conference].”
But Shepard was determined to return to the mound and follow the career path of Brendan, who was drafted by the Red Sox in the 28th round in the 2011 draft and is now pitching in the Gulf Coast League with the Boston organization. He was the first Stonehill player to be drafted by a Major League club.
This season, as a senior, Kyle was back on the hill, throwing to his younger brother, Colin , a sophomore catcher who had transferred to Stonehill from Division 1 Bryant.
That comfort, coupled with the hard work of pitching coach Nick SantaBarbara , had Shepard clicking his fastball in the low 90s as he mowed down 53 batters in 49⅔ innings, compiling a 4-2 record with a 4.17 earned run average.
“I took a couple of extra months to get ready,” said Shepard. “I wanted to devote myself to pitching and it really paid off for me.”
Shepard went about his business and continued to get stronger
“The potential that Kyle has, considering he hasn’t been a pitcher for almost four years now, was what opened up the scouts’ eyes,” said Boen. “Once you could see Kyle getting comfortable on the mound, the scouts saw a left-handed pitcher with the right length and body type and a fastball consistently hitting 89-91 after not pitching for four years. It really opened up their eyes to what he could down the road.”
Four days after receiving that phone call from Sherman, Shepard was at the Cubs spring training facility in Mesa, Ariz., filling out paperwork and going through testing from team doctors.
As he waited to officially begin his professional baseball career in the rookie-level Arizona League, he had that same calm demeanor that allowed him to sit through three days of a draft in which he was not selected.
Once again, Kyle Shepard has a plan: Continue to improve, take it one day at a time, and enjoy the ride.