Caleb Wilfinger

Deputy Editor
Caleb is a Deputy Editor at Pickswise who resides in Upper Manhattan and has spent time in Philadelphia and Washington, D.C. He has been handicapping various sports since 2018, including NFL, NCAAF, NBA, NCAAB, MLB and tennis. The futures market is his favorite to target and he has a passion for sharing his plays with the Pickswise community.
Live Picks 3
Live Parlays 1
Weekly News Articles 6
Location
New York
Favorite Sports
Favorite Teams
Kansas Jayhawks
Los Angeles Dodgers
New York Giants
New York Knicks
Greatest Betting Win
One of my favorite sports betting memories was certainly in October of 2022, when I successfully cashed a 5-team Round Robin parlay involving games I had already played as straight bets. It involved Penn State catching 16 at home against Ohio State, along with Notre Dame, UCF, Louisville and Baylor all on the money line as underdogs. The Irish and Cardinals took care of business early by crushing their opponents and Penn State hung tough to cover the inflated number against the Buckeyes. Meanwhile UCF pulled out a thriller against Cincinnati, leaving me only a Baylor victory away from a serious 50U profit. Thankfully, the Bears made quick work of Texas Tech in the second half and I was able to watch the 4th quarter with a smile on my face. This was one of three 5-leg Round Robin parlays I cashed during the 2022 college football campaign, as part of what was a terrific season on the gridiron.
Greatest Achievements
Finished with a win rate of 63% in weekly 2022 NCAAF best bets column, highlighted by an 8-0 run to close out championship week and bowl season 25-8 (76%) YRFI/NRFI run from June through August 2023.
Education
Caleb attended Penn State University, where he covered Penn State football and basketball for 3 years (along with many other sports), getting an up close and personal look at the grind of a full collegiate athletics regular season. His two bachelor's degrees were in Journalism & Political Science, with sports journalism as a primary focus. During his senior year, Caleb began moving away from betting casually and turning into a sharper bettor, including creating systems, compiling data for multiple sports, etc.
Experience
5+ years betting experience 3+ years as a sports handicapper 10+ years as a sports journalist Caleb has been betting legally since 2019 but his history with gambling predates that, as he regularly picked NFL games against the spread throughout his college tenure. In 2021, Caleb started handicapping college football games for Pickswise and turned a profit for the season. After moving into a full-time Deputy Editor role in 2022, Caleb has had plenty of success and winners for the site’s users, most notably in college football, NFL and the MLB YRFI/NRFI market.
Favorite betting market / type
Futures and Point Spreads.
Favorite bookmakers
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Caleb's Picks

Caleb's Parlays

Tuesday's MLB mega parlay
Yesterday
Los Angeles Dodgers
San Francisco Giants
LA Dodgers @ SF Giants · Run Line
LA Dodgers -1.5
Our Analysis

To start off our MLB parlay, I’m going with the Los Angeles Dodgers on the run line. It might have taken a little while to get to this point, but the Dodgers are right where most experts expected this season. Los Angeles is currently leading the NL West and looks every bit the part of a World Series favorite, particularly now that Shohei Ohtani is back in the lineup. Furthermore, Dave Roberts’ team is 5-2 this season when Gavin Stone takes the mound, which is what we’re getting on Tuesday. Los Angeles will also get the pleasure of taking on Keaton Winn, who has given up a ton of hard contact this season (bottom 2 percentile among all qualified pitchers) and holds an ERA of 5.63 on the campaign. Let’s back the Dodgers to win by at least 2 runs in this rivalry matchup.

Chicago Cubs
Atlanta Braves
CHI Cubs @ ATL Braves · Game Totals
Under 8.0
Our Analysis

For the second leg in our MLB parlay, I’m going with this National League matchup to stay under the total. Simply put, this game is all about the starting pitchers. Jameson Taillon has been a total surprise for the Cubs, posting an ERA of 1.13 on the season, to go along with an xWOBA, WOBACON (quality of contact by opposing hitters) and xERA all within the top 5 percentile of qualified pitchers this season. On the other side, Chris Sale has quietly been dealing with his new club, with an xERA of 2.85 and terrific marks in hard-hit rate and average exit velocity from opposing hitters. Given the prowess of these pitchers, it’s hard to imagine a high-scoring affair in Atlanta on Tuesday. With that in mind, let’s back the under in what should be a terrific game.

Toronto Blue Jays
Baltimore Orioles
TOR Blue Jays @ BAL Orioles · Run Line
BAL Orioles -1.5
Our Analysis

To close it out this MLB parlay, I’m going to be backing the Baltimore Orioles on the run line. Baltimore is one of the best teams in baseball and it all starts with its young offense, which ranks inside the top 10 in nearly every major batting category this season. However, what has been most encouraging for the Orioles chances at winning the AL East has been their tremendous starting pitching. Corbin Burnes has been every bit the ace that he was promised to be, but Kyle Bradish has arguably been even better to this point. Bradish (1.86 ERA) should continue to thrive on Tuesday against a Blue Jays lineup that is currently 23rd in OPS and 25th in slugging percentage for the season. On the other side, Chris Bassitt (5.06 ERA) has struggled mightily and I don’t expect that to change in this matchup. Let’s get to the window with the Orioles on Tuesday.

Caleb Wilfinger

Caleb's Analysis