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 10
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

Friday's MLB mega parlay
Yesterday
Tampa Bay Rays
Boston Red Sox
TB Rays @ BOS Red Sox · Money Line
BOS Red Sox Win
Our Analysis

To start off our MLB parlay, let’s take the Red Sox on the money line. This is a massive series in the AL Wild Card picture, and it came down to the wire on Thursday, when Boston rallied late to steal the series opener. Winners of 9 of their last 10, the Red Sox should be in a solid position to keep the good times rolling on Friday, especially since their offense is averaging 7.7 runs per game with a .938 OPS over the past 2 weeks, and Alex Bregman is set to return on Friday. Neither starter is expected to go that deep into this game, but Red Sox starter Hunter Dobbins has been much better at home (3.22 ERA) and Drew Rasmussen is due for some regression (3.68 xERA compared to his 2.82 actual ERA) in his upcoming outings. Let’s take Boston to keep the train rolling at home.

Los Angeles Dodgers
San Francisco Giants
LA Dodgers @ SF Giants · First 5 Innings Line
SF Giants F5 -0.5
Our Analysis

For the 2nd leg of our MLB parlay, we’re off to San Francisco for a matchup between the Giants and the suddenly reeling Los Angeles Dodgers. Los Angeles’ offense has struggled mightily of late (5 runs over its last 4 games), and I don’t see the Dodgers succeeding much against the excellent Logan Webb (2.62 ERA, 27.2% strikeout rate, 90th percentile ground-ball rate) on the road. On the other side, Dustin May will get the ball for Los Angeles on Friday, and the lanky southpaw has been pretty unconvincing this season, posting a 4.52 ERA on the year, to go along with a 5.67 ERA in June. All things considered, the Giants should be able to get out to an early lead and hold the edge through 5 innings on Friday.

Seattle Mariners
Detroit Tigers
SEA Mariners @ DET Tigers · Run Line
DET Tigers -1.5
Our Analysis

To close out our MLB parlay, let’s back the Tigers on the run line. Detroit is taking on a Seattle Mariners team that suffered a heartbreaking loss on Thursday, and will now have the displeasure of facing off against Tarik Skubal (2.02 ERA, 0.81 WHIP, 33.9% strikeout rate), who is the AL Cy Young favorite for the 2nd straight season. As for the Seattle side of things, the Mariners are countering with Luis Castillo, whose underlying metrics are just not as good as his baseline statistics at this point in the campaign. That’s certainly concerning against a Tigers lineup that is ranked 6th in SLG and OPS on the year. With Detroit having the vastly superior starter and a pretty well-rested bullpen, I’ll gladly back the Tigers to win by margin on Friday.

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Caleb Wilfinger

Caleb's Analysis