Caleb Wilfinger

Deputy Editor
Google News
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 0
Live Parlays 3
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
Read More

Caleb's Parlays

Saturday's NBA Parlay
Today
Detroit Pistons
Minnesota Timberwolves
DET Pistons @ MIN Timberwolves · Point Spread
MIN Timberwolves -2.0
Our Analysis

Detroit improved to 9-3 SU in games without Cade Cunningham as they ran over the New Orleans Pelicans 129-108 in their last game. It was a much needed bounce back performance after a heartbreaking loss in OT vs Atlanta before that, Jalen Duren made sure his team would win with 30 points and 10 boards on Thursday. Now the Pistons face a tough Minnesota Timberwolves challenge and Duren is on the injury report along with Marcus Sasser, Tobias Harris and Ausar Thompson. Detroit’s depth will be put to the test here, it’s likely that at least a couple of those guys will be out for Saturday’s game. They’ve not had the best of times in games against the T’Wolves lately, winning just 3 of the last 11 meetings.

Minnesota is in a similar situation with their best player Anthony Edwards being out. They too have shown great resilience winning their last 2 games against the Celtics and Rockets without him, which is a massive confidence booster with less than 10 games remaining in the regular season. The 15-0 run to overturn a 13-point deficit in the OT against the Rockets was something else, it’ll be interesting to see how much energy they have left after that performance. Julius Randle, Jaden McDaniels, Donte DiVincenzo and Bones Hyland have all taken turns leading this team on the scoring front in Ant’s absence, if you are the Pistons it might be difficult to come up with a defensive scheme as you simply don’t know where the danger is coming from.

I was really impressed with what I saw from Minnesota in their last game, I think playing at home is what will give them the edge here. There’s a lot of fight in this team, especially with Ant Man out of the line-up. The same can be said about the Pistons with Cade not playing, but they have just too many players on the injury report for my liking here. I’ll side with the home team.

Detroit Pistons vs Minnesota Timberwolves Predictions: Timberwolves -2 is available at time of publishing. Playable at that number.

Philadelphia 76ers
Charlotte Hornets
PHI 76ers @ CHA Hornets · Game Totals
Under 233.0
Our Analysis

The Philadelphia 76ers travel to face the Charlotte Hornets in a matchup heavily influenced by injury uncertainty and overall game environment. Philadelphia has shown flashes of elite offense, including a 157 point outing, but consistency depends heavily on availability. Tyrese Maxey, who averages 29.0 points and 6.7 assists, is dealing with a finger injury and is a true game time decision, while Kelly Oubre Jr. is also questionable. If Maxey is ruled out, it significantly lowers Philadelphia’s offensive ceiling, as he is their primary creator and pace driver, creating a potential buy high spot on the total if the number does not adjust.

The Charlotte Hornets enter with a healthier roster and a more stable offensive structure, but they are not an explosive scoring team. They rely on balanced production and operate at a moderate pace, often settling into half court sets that limit possessions. Against a potentially shorthanded Philadelphia team, especially without Maxey, the pace could slow even further, reducing overall scoring opportunities. Even if Oubre plays, his usage could be limited, adding more uncertainty to the Sixers’ offense. With injury concerns, a possible slowdown in tempo, and fewer efficient scoring chances, this matchup projects as a lower scoring game than the total suggests.

 

76ers vs Hornets Prediction: Under 233 (-110) available at time of publishing. Playable to 232

Utah Jazz
Phoenix Suns
UTA Jazz @ PHX Suns · Point Spread
PHX Suns -14.5
Our Analysis

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This is shaping up as a brutal scheduling spot for Utah, and it’s difficult to see them keeping this one competitive deep into the game. The Jazz are coming off a taxing road back-to-back, having just faced a high-powered Denver team that can stretch defenses and force Utah into uncomfortable rotations. Now they turn around and face a Phoenix squad that brings a completely different—but equally problematic—challenge.

The Suns play with physicality, defensive discipline, and half-court control, which directly counters Utah’s preferred style. The Jazz thrive when they can push pace, create space, and operate freely on offense. Phoenix, however, is built to disrupt that rhythm. They slow games down, contest shots effectively, and force opponents into tougher possessions. Fatigue becomes a major factor here. Utah’s legs are unlikely to hold up after chasing Denver’s offense, and now they must deal with Phoenix’s defensive pressure. That combination often leads to scoring droughts and poor shot selection. This projects as a mismatch in both energy and execution. If the Suns impose their will early, this could get out of hand quickly. Laying the points is justified.

Jazz vs Suns prediction: Phoenix Suns -14.5 (-110) available at time of publishing. Playable to -15.

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Saturday's MLB parlay
Today
Pittsburgh Pirates
New York Mets
PIT Pirates @ NY Mets · Money Line
NY Mets Win
Our Analysis

As I will mention countless times this season, I am a fan of the Pittsburgh Pirates. This offseason was something Pittsburgh fans have been waiting for, and that was a sign that the team was at least trying to compete. Pittsburgh signed their first multi-year free agent since 2016 by inking Ryan O’Hearn to a 2-year deal. They acquired Brandon Lowe, Jake Mangum, and Mason Montgomery from Tampa Bay in a deal involving Mike Burrows. Marcell Ozuna was signed to fill the DH spot, and Gregory Soto was brought in to fill a large role in the bullpen. Konner Griffin will be on the roster eventually this season, as will top 100 prospect Jhostynxon Garcia. For the first time in years Pirate fans have reason for hope, and 2026 should be a more competitive season for the organization.

The New York Mets also had an eventful offseason, bringing in Bo Bichette, Marcus Semien, Jorge Polanco, and Luis Robert Jr for a new look lineup. Their pitching staff added Freddy Peralta, Tobias Myers, Luke Weaver and Devin Williams as well. They did say goodbye to longtime Mets in Pete Alonso, Jeff McNeil, and Brandon Nimmo, but the roster does seem to be in a better place on paper heading into 2026.

New York grabbed Game 1 of this opening series by an 11-7 final score. Mishaps by Oneil Cruz resulted in 4 early runs, and Paul Skenes was only able to register 2 outs in that start. While I have high hopes for Pittsburgh this season personally, I do have concerns for Saturday’s matchup. The Pirates traded defensive flexibility for offensive firepower this offseason, and many critics believe this could be a bottom 5 defensive unit in the sport this season as a result. This puts a ton of pressure on the pitching staff to perform, especially in the strikeout department. Mitch Keller is a steady arm, but he relies heavily on the defense behind him given his ground ball nature.

Another concern of the Pirates this season is their lineup when facing left-handed pitching. It will be interesting to see if they tend to roll with a bench-heavy right-handed lineup, or if they let their higher paid lefty bats take their lumps against southpaw pitching. David Peterson will be the first southpaw to test this Pirates unit, and I believe he will find some success in this spot. The pitching environment is also solid for this matchup with temperatures in the mid to low 40’s during game time. While this is a game I would rather watch than bet on, I do lean towards a Mets win on Saturday.

Pittsburgh Pirates vs New York Mets prediction: Mets ML (-168) available at time of publishing. Playable to -170 odds.

 

Chicago White Sox
Milwaukee Brewers
CHI White Sox @ MIL Brewers · Run Line
MIL Brewers -1.5
Our Analysis

The Chicago White Sox were bounced 14-2 in Thursday’s opener, which is not exactly what the team envisioned, as the team is expected to be slightly better than recent seasons. That’s a tough start. The White Sox won just 60 games in 2025, and they were just 21-27. RHP Sean Burke takes the ball trying to get things on track properly. He was 4-11 with a 4.29 ERA with a 1.45 WHIP last season, and was just 0-6 with a 4.74 ERA across 57 IP with 11 homers allowed and a .258 opponent batting average in eight road starts and four relief appearances.

For the Brewers, RHP Chad Patrick made his MLB debut with a 3-8 record, 3.53 ERA and 1.28 WHIP across 23 starts and four relief appearances, striking out 127 batters in just 119 2/3 IP. He was solid working at American Family Field, going 2-4 with a 2.94 ERA with a .235 opponent batting average with 7 homers allowed in 67 1/3 IP in 12 starts at home with 3 relief appearances. As such, let’s back the Brewers to get the job done at home, and we’ll lay the run and a half at plus-money rather than pay up on the money line.

White Sox vs Brewers prediction: Brewers -1.5 (+110) at time of publishing. Playable to -110.

Cleveland Guardians
Seattle Mariners
CLE Guardians @ SEA Mariners · Run Line
SEA Mariners -1.5
Our Analysis

The Cleveland Guardians and Seattle Mariners are set for the 3rd game of their 4 game series on Saturday night at T-Mobile Park. Cleveland took the season opener 6-4 on Thursday while Seattle responded with a 5-1 win on Friday. The starting pitching matchup in this one pits Cleveland’s Joey Cantillo against Seattle’s Bryan Woo, and the edge goes to Woo. The 26-year-old right-hander emerged into one of the most consistent starting pitchers in baseball last season as he posted a strong 2.94 ERA and racked up 198 strikeouts over the course of 186.2 innings of work. Woo has only faced the Guardians once in his career, which came back on June 19 of the 2024 season. He has improved vastly since then, and should be able to put together a strong outing in this one.

Aside from Jose Ramirez, this Guardians lineup is tough to predict on a night-in and night-out basis. Cleveland racked up 12 hits in the opener but had just 4 hits in Friday’s matchup. Offensive consistency may be hard to come by for the Guardians this season, and they have a tough matchup going up against such a reliable starter in Woo. Backing the Mariners on the run line is the play in this matchup.

Guardians vs Mariners prediction: Mariners -1.5 (+120) available at time of publishing. Playable at that number.

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Saturday's college basketball parlay
Today
Purdue Boilermakers
Arizona Wildcats - NCAAB
Purdue @ Arizona · Point Spread
Arizona -6.0
Our Analysis

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The West Regional in San Jose features the top 2 seeds on Saturday night as the Arizona Wildcats face the Purdue Boilermakers. We have a trip to the Final Four on the line, and both clubs are obviously playing their best basketball of the year. Arizona has looked every bit the part of a title contender each step of the way, while Purdue has had a couple of dogfights but continues to come out on top. On Saturday night, the Wildcats are favored by 6 points, and lots of money is flowing toward the underdog. I think Arizona is just that good, and I am going to keep riding with them.

Purdue does a lot of things well. The problem in this game is that Arizona does all those things better. Purdue is a dominant team on the glass; Arizona is better. Purdue shoots the 3-ball well; Arizona defends it well. Purdue scores well around the basket; Arizona protects the rim better than anyone. Neither team turns it over much, and the Purdue identity is built around being the #1 team in the country for offensive efficiency. But what happens when they run into a top-3 defense? If Purdue is stymied at all, they will be in trouble, because Arizona will not be slowed down. No one has slowed down their multi-level attack yet, and if you are going to beat them, you just have to outdo them at it. I don’t see it. Arizona wins, and I think they cover too.

Purdue vs Arizona Prediction: Arizona -6 (-110) available at the time of publishing. Playable to -7.

Iowa Hawkeyes
Illinois Fighting Illini
Iowa @ Illinois · Point Spread
Illinois Win -7.0
Our Analysis

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A pair of Big Ten teams are set to face off in the Elite Eight as the #2 seed Illinois Fighting Illini take on the #9 seed Iowa Hawkeyes. Illinois was terrific in its win over Houston, shooting 43.1% from the floor and dominating the glass, 43-34. This is a loaded Illini team with five players averaging double figures, but all eyes will be on Keaton Wagler and his ability to lead them to the Final Four. Wagler is averaging 17.7 points and 5.1 rebounds per game, while David Mirkovic provides a strong interior presence inside with 13.7 points and 8 rebounds per game – something Iowa will need to account for defensively.  

For Iowa, Bennett Stirtz is coming off his best performance of the tournament, scoring 20 points with four assists against Nebraska. However, he struggled in the earlier matchup against Illinois, finishing with just 12 points on 5-of-17 shooting. According to KenPom, Illinois ranks 21st in adjusted defensive efficiency (97.5) compared to Iowa who ranks 32nd (99.9). Offensively, Illinois ranks 2nd (131.4) and Iowa 20th (123.8). When these two teams met earlier in the season, Illinois walked away with a 75-69 victory. The Illini did a great job at controlling the boards but committed 12 turnovers, which led to easy transition points for Iowa. If Illinois can clean up those mistakes and limit turnovers, their size, depth, and offensive efficiency should give them the edge. After seeing how Illinois handled Houston’s physical defense, they appear well-positioned to handle Iowa’s pressure and control this game. Look for the Fighting Illini to take over down the stretch and punch their ticket to the Final Four. 

Iowa vs Illinois prediction: Illinois -7 (-115) available at time of publishing. Playable at that number.

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Caleb's Analysis