His older brother, 22-year-old Matthew Winckowski, had just died of an accidental drug overdose.
“He was two months away from graduating with a Commercial Arts degree,” Winckowski explained. “He was trying to start his own clothing line.”
Casey and Matthew were tight knit, so the sudden loss of his only sibling struck the former’s heart right to the core.
“We were real close,” Winckowski said. “We did everything together. He was at the City League Championship game (a 4-3 league winner for Clay at Fifth-Third Field).”
It was a sudden, jolting downturn for Winckowski at a time when he was coming off a brilliant prep baseball career at Clay, and had an exciting future of college ball on deck at Owens Community College.
“It was hard because he passed away two weeks before we were scheduled to leave for our spring trip,” he said. “I was thinking about not playing the season.”
His new teammates, a number of them former local adversaries on the diamond, and his family encouraged him to move forward.
“My family reminded me that Matt would have wanted me to play,” said Winckowski, “and our team had his initials embroidered on our hats.”
The advice proved to be rewarding.
Winckowski wound up pitching eight innings and hitting a national 12th best .491 in 53 at-bats while playing third base in 23 games for Owens. The Express steamed to the Ohio Community College Athletic Conference title at 14-2, with a sparkling 31-6-1 overall record last spring.
“Matt was at every game watching over me,” Winckowski said. “I had one of the best first years I could have asked for.”
Winckowski followed his solid freshman college season by playing for the summer federation wood bat baseball Ohio Monarchs Gold in the City of Toledo Federation League.
Winckowski’s collegiate success, and the presence of victory, followed him through June and July.
He played in left for the Monarchs and hit .336 in a team-high 128 at-bats, clubbing two homers and driving in 28 runs.
The Monarchs won the league and earned the bid right to play host in the 2008 National Amateur Baseball Federation College Wood Bat World Series played August 7-11 at Ned Skeldon Stadium in Maumee, University of Toledo Scott Park, and Bowman Field and Joe E. Brown Field in Toledo.
After losing one of three games in pool A, the Monarchs reeled off a seemingly destined run from the quarterfinals to the NABF CWS championship, bringing Northwest Ohio its first federation ball college division national title.
In a 7-2 semifinal win over the Maryland (Balt.) Orioles, Winckowski made a crucial diving catch in left-center field later in the game to help the Monarchs advance.
In the championship game against the defending champion Long Island (N.Y.) Astros, Wincowski provided the ultimate clutch play in the most dramatic way possible.
The Monarchs trailed 3-0 after an inning and a half, but crawled back into the game with Jake Cappeletty tying the score 3-3 on a homerun in the bottom of the eighth.
In the last of the ninth, with men on first and second and two outs, Winckowski, hitting under .300 in the tournament at that point, came to the plate.
Winckowski worked his way to a 3-2 count, and then lined a shot over the fielder’s outreached glove in deep left to plate the World Series-winning run.
“It was just my time,” he said. “(The pitcher) left that pitch up and in and I was just able to turn on it, with my brother watching over me. It was probably one of the best at-bats I’ve ever had in my life.”
The Monarchs, fully aware of Winckowski’s situation, were pulling for him to do what he ended up doing, knowing it would mean something well beyond the confines of that legendary old home of the Toledo Mud Hens.
“It was a real important moment for him,” said teammate and former Genoa star Cory Hornyak. “I knew he was to hit the crap out of the ball.
“It was huge for us, but it was also huge for him. He showed what he’s got.”
Winckowski now has a brilliant remaining three seasons of college baseball awaiting him. With the Express having graduated a number of its starters in 2008, he is likely taking over the starting slot at third on a full-time basis.
“We’re going to have a lot of new faces,” Winckowski said. “We’ll be a very young team, so I want to step in and be a leader, show the new guys what the college game is all about. This summer made me a much better player.”