Whenever Chris Roof reaches a milestone his first words to a question about it are: "Bill Howard."
Howard was Roof's head coach when Roof played his baseball at Governor Livingston before graduating in 1992.
Roof, 51, has said time and again that it was Howard who shaped the player he was on his way to excelling collegiately at Montclair State. Howard has also been a major influence on how Roof handles his coaching duties.
At the helm of the Highlanders since 2004 after three years as the head coach at Millburn, Roof became just the fifth baseball coach in Union County history to reach 500 victories on Thursday, May 29, when top-seeded GL scored the game's final six runs en route to a 12-6 victory over ninth-seeded South River in the Central Jersey, Group 2 quarterfinal played at Snyder Park in Berkeley Heights.
The top five winningest coaches in Union County are: Bob Brewster (655), Ray Korn (651), Gordon LeMatty (641), Dennis McCaffery (527, including 16 so far this year) and Chris Roof (500, including 24 so far this year).
After serving as the head coach at Cranford from 1999-2024, this is McCaffery's first season as the head coach at St. Joseph's, Metuchen.
McCaffery's squad edged Immaculata, 5-4, in a South Jersey, Group A quarterfinal on Friday (May 30).
This is Roof's 21st season at GL, with his Highlanders next playing on Tuesday, June 3, in a CJG2 semifinal at home against fifth-seeded Raritan which edged 13th-seeded Cinnaminson, 2-1, also on Friday.
The other June 3 semifinal is 14th-seeded Bordentown at second-seeded Robbinsville. The final at the higher seed is set for Thursday, June 5.
Howard guided GL to its first state championship, the Group 2 crown in 1999. Roof was also an assistant coach on Howard's staff in 1996 when GL reached its first Union County Tournament championship game.
"Bill Howard taught us how to be men," Roof said.
Roof has guided GL to Group 2 state championships in 2011, 2015 and 2024 and to a second-place finish in 2006. At the moment GL is attempting to repeat as CJG2 and Group 2 state champs for the first time. Earlier this month the Highlanders repeated as UCT champions for the first time.
"Getting to 500 wins is a culmination of everything," said Roof, who won his 300th game 10 years ago in 2015 when GL defeated Bernards 10-4 in the Group 2 state championship game at Toms River South. That was the first GL team to win 28 games (28-6). Last year's squad was the second (28-5).
"I'm so blessed to be a part of this program and I'm happy for both (Berkeley Heights and Mountainside) communities; it means the world to me," Roof said. "This is home for me. I love it.
"I have really good players who are also good kids. Many of the coaches on staff here have been with me for a long time."
GL is now 24-0 overall and finished 11-0 in capturing the Union County Conference's Watchung Division title. Then came a second straight and fifth overall UCT crown as the top-seeded Highlanders outscored four opponents 49-0 and did not allow a hit in the championship game.
"For me and my staff, at the end of the day it's all about how we've developed these young men, so that they will be ready for college and to move on," Roof said. "When these kids are on their own it's about them making the right decisions. Winning is great and as coaches we get into coaching to win, but the winning is gravy."
GL came back from a 5-1 deficit to oust 16th-seeded Point Pleasant Boro 7-6 in its first-round game played at home on Tuesday, May 27. GL's previous five wins were by shutout. The Highlanders entered state tournament play at 22-0, with 13 shutout victories and had given up only 31 runs.
GL is now 4-0 in one run games, its first three being 1-0 at Brearley on April 16, 8-7 at home vs. Westfield on Apri 21 and then 1-0 over Elizabeth in the May 17 UCT semifinals at Johnson.
"Our first two games say a lot about our section," Roof said. "Point Pleasant Boro is a really good team that plays in a tough Shore Conference. We could have folded when we were down 5-1, but our team never gives up. We needed a challenge like that. We didn't have too many of them during the season."
It doesn't matter that GL is undefeated. Nobody cares that the Highlanders, for the first time in program history, are ranked No. 1 in New Jersey this late in the season.
GL has now won a program-record 30 games in a row dating back to last season, but that will be of no concern to the opponent the Highlanders face on Tuesday.
"It's cool that we got to June undefeated," Roof said. "However, the section that we're in is very challenging to say the least."
Junior right-hander Keith Mann (8-0), who pitched in relief of senior righty Matty Diskin against PPB, will get the start on Tuesday, according to Roof.
Diskin is still a prominent batter in GL's starting lineup as the team's designated hitter, but after his injury against PPB he is no longer available to pitch for the rest of the season.
Roof started senior right-hander Anthony DeNora against South River. DeNora is Roof's No. 1 relief pitcher.
"If we're fortunate enough to make it past Tuesday then we'll have to piece it together for the final," Roof said.
UNION COUNTY'S TOP 5 WINNINGEST BASEBALL COACHES:
Bob Brewster: 655-342-3 (.657)
1983-2021 – 38 seasons at Westfield
Brewster has guided the Blue Devils to Group 4 state championship games in 2011 (Toms River South), 2013 (Toms River North) and 2018 (Veterans Park, Hamilton).
Brewster has led Westfield to all five of its North 2, Group 4 titles: 1988, 2011,
2013, 2018, 2019.
Brewster has also led Westfield to 11 UCT championships, tied for the most by any coach,
with his last coming in 2017.
Ray Korn: 651-308-1 (.679)
1974-1979 – 6 seasons at Roselle Catholic
1 state championship – Parochial A in 1978
1980-2009 – 29 seasons (he did not coach one of those years, 2002) at Elizabeth
3 state championships – Group 4 in 1983, 1986 and 1994
Korn also guided Elizabeth to Union County Tournament
championships in 1983, 1985, 1989, 1991 and 2008.
Korn was 110-91 in his six seasons at Roselle Catholic.
Gordon LeMatty: 641-272-4 (.702)
1959-1991 – 33 seasons at Union
2 state championships – Group 4 in 1972 and 1974
LeMatty also guided Union to Central, Group 4 state titles in 1966 and 1968
and the Farmers to the first seven of their eight UCT championships, the last one
coming in 1975. In addition, LeMatty led Union to the 1966 and 1970
Greater Newark Tournament crowns.
Dennis McCaffery: 527-160-1 (.767)
1999-2024: 25 seasons at Cranford (there was no season in 2020 because of COVID)
McCaffery's record at Cranford was 511-154-1 (.768)
2025: 1 season at St, Joseph's, Metuchen (16-6 as of May 30)
3 state championships – Group 3 in 2010 (won at Toms River North), 2012 (won at Toms River South) and 2013 (won at Toms River East)
8 state championship games – 0-1 at East Brunswick Tech, 3-3 in Toms River and 0-1 in Hamilton
McCaffery guided Cranford to all 11 of its Union County Tournament championships and closed with an 11-1 record in the UCT final. McCaffery and Bob Brewster of Westfield are tied at 11 for the most UCT championships won.
Cranford finished No. 1 in New Jersey in 2013 with a 25-1 record. At 17-0 Cranford lost at Westfield 2-1 for its lone setback. Cranford split with Westfield in division games that season and also beat the Blue Devils in the UCT final.
This season McCaffery guided St. Joseph's to the Greater Middlesex County (GMC) tournament championship.
Chris Roof: 500-184-1 (.731)
2004-2025: 21 seasons at Gov. Livingston
Roof's 21-season record at GL so far is 446-150-1 (.748)
Roof’s 3-season (2001-2003) record at Millburn was 54-34 (.614).
3 state championships - Group 2 in 2011 (won at Toms River North), 2-15 (won at Toms River South) and 2024 (first Union County team to win at Veterans Park in Hamilton).
4 state championship games - 1-1 at Toms River South, 1-0 at Toms River North and 1-0 at Veterans Park, Hamilton
Roof guided GL to all five of its Union County Tournament championships and has a 5-5 record in the title contest. Titles won: 2016, 2018, 2021, 2024 and 2025. Title-game losses: 2007, 2011, 2014, 2015, 2023.
Program record for wins in a season is 28: in 2015 (28-6) and in 2024 (28-5, four losses by one run).
GL repeated as UCT champs for the first time this season.